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27 Awesome Chicago Neighborhood Staycations

By Staff in Arts & Entertainment on May 23, 2017 3:00PM

Call us homebodies, but we see few reasons to shell out for pricey summer airfares and gas money when the promise of an affordable, relaxing staycation beckons. With summer on the way and at least 77 Chicago neighborhoods to explore (yes, some would argue there's a lot more), we've sketched out some of our ideal neighborhood staycation plans—and kept Chicago's more obvious go-to vacation destinations like the Art Institute and Millennium Park out of the running, so our staff could get creative.

Here's the premise we gave ourselves in 2015 and again in 2016: You have a day with no obligations, a vacation-worthy budget and utterly no desire to leave your neighborhood or run afoul of a downtown Segway tour. Where do you go? Some of us had trouble choosing (an evening at Thalia Hall, or Pilsen's Gallery Night?) but the good news is Chicago is a city of neighborhoods, and you can mix and match these picks to your heart's content. Or you can venture further and report back to us about your favorite neighborhood staycation activities. After two years of writing down our favorite ideas, we give you the complete (for now) list of 27 neighborhood staycations:

Stoney Island Arts Bank, via Jessica Mlinaric / Chicagoist

Greater Grand Crossing

Visit Stony Island Arts Bank

One of Chicago’s most renowned artists, Theaster Gates often works at the intersection of art and community development—community development not as code for gentrification, but something more progressive and self-governed. The best example, we think, is the Stony Island Arts Bank. Gates purchased the site, a former savings and loan building that had fallen into disrepair, in 2012 for the grand sum of $1. The center now houses four noteworthy libraries: a collection of books and periodicals from Jet and Ebony publisher Johnson Publishing; an archive of thousands of art-historical slides, dating back to prehistory; a collection of racist “negrobilia” objects; and, our favorite, the awe-inspiring vinyl collection of house-music pioneer Frankie Knuckles. Next time some local government functionary tells you electronic music isn’t art, you’ll know where to send ‘em.
Stony Island Arts Bank is located at 6760 S. Stony Island Ave.

Catch a movie at Black Cinema House
Also operated in conjunctions with Gates’ Rebuild Foundation, Black Cinema House holds screenings of films “by and about the people of the African diaspora;” and the organization’s programmers—which have included notables such as Michael W. Phillips and Amir George—strikes a rare balance of adventurousness and approachability. Focus ranges from neglected-but-vital early African-American film to experimental short programs to student works developed through BCH’s neighborhood youth outreach classes. Fresh critical perspectives on more pop-culturally prominent flicks are common, too: recent Diana Ross and Spike Lee retrospectives come to mind. They do frequent screenings at other venues in and around the neighborhood, too, so a quick Twitter or Facebook follow is highly recommended.
Black Cinema House is located at 7200 S Kimbark Ave.

Eat at Original Soul Vegetarian
Any diners operating under the assumption that “vegetarian soul food” is an oxymoron would be wise to visit this beloved vegan-focused outpost. The hands-down standout is the BBQ Twist—a perfect match of sweet sauce and savory riblet-style protein that we’ve waxed poetic about before. The full, meaty texture puts most meat substitutes to shame. And if there are any omnivores in the group, save stomach real estate for real-meat rib tips and hot links at one of the city’s longest-running barbecue spots, Lem’s Bar-B-Q, located just one block east. I know it sounds like a one-or-the-other proposition, but unless you’re a strict-observing vegetarian, it’s the way to go.
Original Soul Vegetarian is located at 203 E. 75th St.
—Stephen Gossett


Eat at Glenn's Diner
Instead of agonizing over the age-old dining question, "cereal or fish?" Glenn's Diner lets you have it all with generous portions in an unfussy atmosphere. For over ten years, the casual neighborhood staple has been serving breakfast all day as well as fresh fish and seafood for lunch and dinner. Eyeing the cereal bar is like taking a nostalgia trip (Golden Crisp! Kix!). Giant chalkboards display underwater options like Arctic char with shrimp diablo sauce and sea scallops dressed with a bacon, mushroom, and sherry cream. If you're not sure where to start, the knowledgeable staff will walk you through every fin on the menu. Don't miss the Cioppino, a San Francisco stew that packs four kinds of fish, shrimp, mussels, and veggies in a light, spicy broth.
Glenn's Diner is located at 1820 W. Montrose Ave.

Drink at Band of Bohemia
Bohemians live and create by their own rules, as do the owners of the namesake Ravenswood restaurant. Co-founders Michael Carroll and Craig Sindelar are Alinea veterans who melded their considerable experience to create a "culinary brewhouse" that's upscale but not stuffy. The small plates menu pairs meals with in-house beers, and not the other way around. Expect unique flavors on tap like a Thai-influenced saison or a Belgian brewed with lemongrass, cardamom, and lavender. The food is impeccable, but just lounging in the gorgeous bar with a seasonal brew or cocktail will wake your inner free spirit.
Band of Bohemia is located at 4710 N. Ravenswood Ave.

Shop at Architectural Artifacts
Architectural Artifacts is quite literally a treasure trove. The 80,000 square foot showroom houses eclectic antiques from around the world that owner Stuart Grannen has been collecting since 1987. Wander the century-old warehouse to explore exquisitely crafted and historically significant pieces like remnants of Buckingham Fountain and a Louis Sullivan column from the Chicago Stock Exchange. Where else can you buy your midcentury Czech light fixtures and vintage Japanese temple ornaments in one place? You might not need that 19th-century Bavarian moose horn hunting lodge chair, but why not treat yo self?
Architectural Artifacts is located at 4325 N. Ravenswood Ave.

Play at Lillstreet Art Center
If Lillstreet were a work of art it would be a mosaic. Since 1975, the co-op has assembled artists of varied ages, skill levels, and disciplines to foster arts growth and education. The 40,000 square foot facility hosts classes in drawing, painting, photography, ceramics, jewelry, printmaking, textiles, and glass. After class, stop by First Slice Pie Café on the ground floor. The nonprofit restaurant's revenue provides meals to more than 600 needy Chicagoans each week. Check out the gallery to see work from the artist in residency program and other makers. When it comes to community building, Lillstreet has it down to a fine art.
Lillstreet Art Center is located at 4401 N Ravenswood Ave.
—Jessica Mlinaric

(from The Revel Room's Facebook)

Wicker Park

Eat at Pub Royale
A restaurant named one of America's 50 best by Bon Appetit hardly needs more accolades. Yet in a neighborhood that sees new openings rise and fall on what feels like a weekly basis, Pub Royale is the best thing that's happened in the past year. The British-Indian pub offers a modern interpretation of the cuisine and plenty of surprises. Eggplant curry and buttered paneer are musts on the dinner menu. Gobi Manchurian, a sweet and spicy helping of crispy cauliflower, is among my favorite dishes in the city. On a less traditional note, check out the India hot chicken served with naan and the royale with cheese, which must be one of Chicago's best burgers. The rotating draft list is eclectic and extensive and the cocktail menu includes refreshing seasonal "royale cups." Eat your heart out, and when you're done there's still brunch!
Pub Royale is located at 2049 W. Division St.

Drink at Revel Room
If the Violet Hour is Wicker Park's place to stand in line for haute cocktails in high back chairs, Revel Room is where you settle into a leather booth for a cocktail on tap. As the Old Style sign out front indicates, this is a casual neighborhood tavern. The library-themed lounge and faded mirrors convey a cozy, chic vibe while the beer list and tap cocktails satisfy discerning drinkers. As with all things at this intersection, opt for a weeknight visit perhaps complimented by live music in the lounge rather than battling the weekend bridge and tunnel crowd.
Revel Room is located at 1566 N. Milwaukee Ave.

Shop at Una Mae's

Una Mae's has been outfitting Wicker Park's hip kids since 1997. Shop the boutique's main floor for distinctive men's and women's clothing, shoes, and accessories. A winding staircase leads you to the sale section while the lower level houses vintage finds. Peruse the personal care products, including herbal steams, natural soaps, and beard oils. Before you hit Milwaukee Avenue, stock up on denim shirts, over-sized sweaters, and statement jewelry at Una Mae's to fit the part.
Una Mae's is located at 1528 N. Milwaukee Ave.

Face the Music
If you haven't visited a rock club or record shop in Wicker Park, you're missing the spirit of the neighborhood. Every night, the Milwaukee, North, and Damen intersection is abuzz with music fans—though somewhat less so now that iconic Double Door no longer anchors the corner. Check the signage outside Subterranean (2011 W. North Ave.) to see which shows patrons are lining up for then post up by the upstairs balcony for the best view in the room. If you're into crate digging, visit vinyl veteran Reckless Records (1379 N. Milwaukee Ave.) at their expanded new storefront. Just down the road, Shuga Records (1276 N. Milwaukee Ave.) specializes in rare and hard-to-find vinyl while Dusty Groove (1120 N. Ashland Ave.) serves up jazz, soul, funk, and hip-hop wax.
—Jessica Mlinaric

Grange Hall Burger Bar, image via Grange Hall's Facebook page

West Loop

Eat at Grange Hall Burger Bar
A few doors down, Au Cheval gets all the glory, but Grange Hall makes a mean, if not meaner, burger without the side of pretentiousness and four-hour wait times of its more-buzzed-about neighbor. The checkered tablecloths and farmhouse vibe in the intimate space feels laid-back but fresh, and a straight forward menu of comfy favorites with a twist—old fashioned waffle fries with blue cheese and Buffalo sauce, anyone?—is hard to resist.
Grange Hall Burger Bar is located at 844 W. Randolph St.

Shop at The Fig Tree
The Fig Tree is the kind of store you find a reason to wander by so you can duck in and explore, and, inevitably, leave armed with a bag of one-of-a-kind goodies from independent artists. There's a distinct sense of humor running through Fig Tree's inventory ("Trump's Small Hand Soap" and a Kanye-decked greeting card captioned "Loving You Is Yeezy," for instance), so just looking around can be a satisfying way to spend part of an afternoon. The largely Chicago-centric stationary, gift and accessories shop is stocked with the card that only your brother-in-law would appreciate, the city flag satchel you've been trying to find and the "West Loop"-scented candle that would make a perfect housewarming gift for your coworker.
The Fig Tree is located at 1037 W. Madison St.

Drink at Bar Siena
If you can handle the throngs of hip West Loopsters crowding into this relatively new space (it opened last year), the buzzy bar may very well be worth your time. Like its sister restaurant Siena Tavern in River North, Bar Siena dishes out some seriously tasty Italian fare, but here it's with a sportier, edgier energy. Bare-bulb light fixtures, rustic brick walls, antique mirrors and other choices establish an overall sense of chic, while suspended flatscreens dotting the walls, an olive tree sculpture and a bright red pizza oven named "Bella" keep things relaxed and interesting at the same time.
Bar Siena is located at 832 W. Randolph St.
—Gwen Purdom

Club Lago, image via Club Lago's Facebook page

River North

Eat at Club Lago
Of course out-of-town Chicago visitors need to try the requisite deep dish and a hot dog with all the classic fixings, but there's a good chance this cozy Italian spot at Orleans and Superior offers a more authentic taste of the city. It's an atmosphere the owners have been honing since 1952, and as the neighborhood has evolved from a warehouse district to an area dotted with art gallery lofts to the condo-dense residential district River North is today, three generations of the same family have kept Club Lago piled high with hearty dishes of red sauce-drenched pasta and simple retro charm. From the neon sign affixed to the side of the brick restaurant to the waitstaff that treat you like an actual old friend, the whole experience feels like burrowing under a warm blanket—topped with bubbly melted parm.
Club Lago is located at 331 W. Superior St.

Drink at The Berkshire Room
Watering holes with a schtick can be off-putting, but The Berkshire Room tucks its nifty novelty item right between the other finely crafted cocktails on its menu. "Dealer's Choice" lets patrons choose a favorite spirit, a preferred flavor profile (think "sweet" or "herbaceous"), and the glassware of their liking, then leaves it up to the bar staff to concoct a one-of-a-kind drink. The results don't disappoint, and neither does the striking, date-friendly space.
The Berkshire Room is located in the ACME Hotel at 15 E. Ohio St.

Shop at Rent the Runway
Yes, technically anyone with internet access can sift through the Rent the Runway racks, but the physical store—one of only five of the previously-online-only retailer's brick-and-mortar locations in the country&8212lets you see, touch and actually try-on a slickly curated array of designer items you really won't find elsewhere. In comparison to your average, or even high-end, department store, the superior quality of the inventory is clear from the moment you stand close enough to spot each embroidered hem or bejeweled detail. Which, of course, is why the goods here are for rent, not purchase (unless of course you want to drop $4,995 on a Kaufman Franco gala gown). The high-tech touches like dressing room mirrors that'll email you photos of the things you tried on, help too. Some finds are hard to justify (if you're spending $175 on a rented dress, why not actually buy one you could wear again?), but some occasions—or perfectly pleated Cedric Charlier jumpsuits&8212are worth the splurge.
Rent the Runway is located at 710 N. Wabash Ave.
—Gwen Purdom

2015_10_08_chicagoauthored.jpg The Chicago History Museum

Old Town

Eat at Kamehachi
They'll have you at spicy edamame. Tossed in garlic and chili oil, Kamehachi's heat-packed twist on the standard Japanese appetizer would be reason enough to visit this Old Town staple. But there are so many more: creative sushi rolls stuffed with out-of-the-ordinary ingredients like citrus wasabi or green beans, outdoor seating in the heart of the neighborhood's walkable epicenter and, if you want to really get into the staycation spirit, staffers that won't judge you for ordering take-out multiple times a week. Trust us.

Explore the Chicago History Museum

It's a little more low key than its flashier, generalist cousins—we're talking about the Field Museum and the Museum of Science and Industry—but that's part of the charm of this aptly named collection of exhibits devoted to none other than our city's history. In addition to covering the basics (Mrs. O'Leary's cow is mentioned somewhere, we're sure), the permanent and visiting displays are always thoughtfully curated, and often they examine Chicago in ways you wouldn't expect. Homages to Chicago artists and designers or creators who were inspired by the city, like photographer Vivian Maier or fashion designer Main Rousseau Bocher, are always a particular highlight and the setting, perched on the edge of Lincoln Park, can't be beat.
The Chicago History Museum is located at 1601 N. Clark St.

Drink at Old Town Ale House
When people describe this place as a dive, they're not kidding. It's dank, dark and more than a little dilapidated. That hasn't kept loyalists (and more than a few celebrity superfans) from packing it nightly, especially after Second City shows let out across the street. Yes, it's cash only and yes, the naked portraits of celebrities and politicians can be unsettling (or hilarious, depending on your mindset and beer count on that particular evening), but it's stuck around for decades for a reason. And we're pretty sure that reason is that Roger Ebert called it "the best bar in the world that I know about," and that guy knew what he was talking about.
Old Town Ale House is located at 219 W. North Ave.
—Gwen Purdom

Taqueria Antotolico, via Facebook

Little Village

Eat at Taquerias Atotonilco
Its hard to determine what the, say, five best dishes are at this long-running taqueria. Truth is, we rarely stray from their specialty: the tacos al pastor, among the best in the city for our money. They’re great any time of day, but are particularly restorative when capping a night out. The original location—a staple on 26th street for 40 years—is open 24 hours on the weekend and until 2 a.m. Monday through Thursday.
Taquerias Atotonilco is located at 3916 W. 26th St.

Drink at Moreno's Liquors
Another decades-rooted neighborhood institution, Moreno's covers all the usual liquor-store essentials, but it stands head and shoulders above the crowd when it comes to the agave market. Moreno's is the largest consumer supplier of tequila and mezcal in Chicago. (The store even sports a mural called “Remembering Mayahuel,” in tribute to the goddess of maguey, painted by students from the nearby Yollocalli Arts Reach.) And while it’s easy to snark on the celebu-branding of tequila and the hipster fad-ishization of mezcal, a walk through the aisles with the ever-knowledgeable staff will open any doubtful mind.
Moreno's Liquors is located at 3724 W. 26th St.

Shop at Numero Factory Outlet
Just when you think every last nugget of buried musical treasure has surely been excavated, local reissue titans Numero Group go and release a jaw-dropping survey of small-press hippie country, or some long out-of-print White Zombie vinyl, or an indispensable collection of regional power-pop or… well, you get the idea. This past July, the archival label added a record store to their warehouse property, where record buyers can peruse all of the label’s countless great offerings. Its crate-digging with a leg up: the best in the business have already done the digging for you.
Numero Factory Outlet is located at 2533 S. Troy St.
—Stephen Gossett

Paul McGee behind the bar at Milk Room. Photo by Clayton Hauck.

The Loop

Visit the Chicago Cultural Center

In a city of world-class museums, the Chicago Cultural Center is no slouch, but it's sometimes overlooked by Loop visitors in favor of the Art Institute and Field Museum. The 120-year-old Chicago landmark has stunning architecture, including intricate stained-glass domes, and a rotating collection of art exhibitions from local and visiting artists. You can plan on catching an afternoon architectural tour of the center, or explore for yourself.
The Cultural Center is located at 78 E. Washington St.

Eat at Revival Food Hall
The Loop has more fast-casual dining options than we can count, but the recently opened Revival Food Hall rivals all of them. The food hall features fast food takes on favorite local restaurants from around the city, including Antique Taco, Smoque BBQ and Black Dog Gelato. Right now we're craving Danke's Secret Sandwich and Black Dog's refreshing cucumber sorbet.
Revival is located at 125 S. Clark St.

Play at Maggie Daley Park
Venture east over Millennium Park's Frank Gehry pedestrian bridge and you'll behold Maggie Daley Park. The whimsical playground is great for staycationers with kids in tow, but even adults can enjoy trampling through the castle-like, all-ages playground (seriously, we've tried this and it's a blast). In the winter, head to the north end of the park for ice skating around Maggie Daley's ice ribbon.

Drink at The Chicago Athletic Association Hotel
When the historic Chicago Athletic Association underwent a massive renovation last year and opened as a boutique hotel stacked with elegant lounges and cozy leather chairs, we knew it was something special. First of all, the place is a gorgeous, modern take on the historic gentleman's club it once was, minus the No Girls Allowed rule it maintained until the 1970s. We recommend drinking at Cindy's, the rooftop bar with sweeping views of Millennium Park, if you can get up there—lines for the elevator ride to the roof often snake through the lobby—or, if you can swing it, Milk Room, which we believe is the best bar in Chicago. Walk-ins are welcome in the lobby's Drawing Room, which also has coffee, snacks and free wifi.
The Chicago Athletic Association is located at 12 S. Michigan Ave.
—Rachel Cromidas

Rogers Park

Play at Loyola Beach
Grab a blanket and a book and head out to Loyola Beach in East Rogers Park. You can lay in the sun or jog or hike along its three-mile trail. And you didn't hear it from us, but the beach became such a popular haunt for Pokemon Go gamers thanks to its proliferation of virtual pokemon, it's earned the nickname Pokemon Beach.
Loyola Beach is located at 1230 W. Greenleaf Ave.

Visit the Leather Archives & Museum
The Leather Archives & Museum is one of Rogers Park's most surprising and obscure open secrets. The museum, historical archive and community space devoted to all things related to the gay leather scene and its influence on Chicago is located in an unassuming, unmarked building on Greenview Avenue. Come for the murals of muscular men that line the walls, stay for the extensive library of the history of the GLBTQ leather community.
the Leather Archives & Museum is located at 6418 N. Greenview Ave.

Drink at Rogers Park Social
The popular neighborhood bar has a seasonal cocktail menu and a retro-style lounge. It's conveniently located near the Morse Red Line station and known for its quality and affordability.
Rogers Park Social is located at 6920 N. Glenwood Ave.
—Rachel Cromidas

Ping Tom Memorial Park, photo via Yelp


Eat at Chi Cafe
Chinatown is an embarrassment of restaurant riches. But instead of spotlighting hyped newcomers like dim-sum house Dolo Restaurant and Bar or famous staples like Lao Sze Chuan, we’re recommending a favorite that, despite less renown, holds our highest enthusiasm. The contemporary-but-cozy atmosphere is perhaps the corridor’s most authentically Shanghai-like environs. It’s open super late (until 2 am during the week and 5am on Friday and Saturday). The food is inexpensive and savory, especially with a dollop of spice seafood sauce XO. All together, they make it among the most “neighborhood” of the neighborhood’s dining options.
Chi Cafe is located at 2160 S Archer Ave.

Drink at Joy Yee Noodles
Yes, savvy reader, this is indeed a “drink” recommendation at a noodle shop. While delicious chow mein and Korean japchae dishes are cheap and liberally portioned (hence the college crowd), the specialties here are the bubble teas and icy-good smoothies. Owner Jennifer Au’s juice-bar drinks—a fruit-smoothie spin on old-style Taiwanese tapioca tea—were among the first of their kind in the city; and the fresh fruit, chewy tapioca and gobsmacking array of menu options still place them ahead of most imitators who followed in her wake.
Joy Yee Noodles is located at 2139 S China Pl.

Visit Tom Ping Memorial Park
This lovely park hideaway, tucked between 18th Street and Wentworth Avenue and nestled along the South Branch Chicago River, has a lot of Park District amenities: gymnasium, indoor pool, playground, fitness center, baseball diamond. It’s also a preferred ship-out point for urban kayakers, with greener scenery and none of the tour-boat/water-taxi obstacle found further north. (Dabblers or rookies can also rent, from on-premises Urban Kayaks.) But we like it best as a place to lazily stroll and sightsee. The converted rail yard is ideal for a riverwalk stroll or a picturesque timeout—either at the Chinese-style pavilion or the hidden-gem Skyline Patio.
Tom Ping Memorial Park is located at 1700 S Wentworth Ave.
Stephen Gossett

Garfield Park Conservatory/By Kristine Sherred

Garfield Park

Eat at Inspiration Kitchens: The well-executed comfort dishes churning out of this nonprofit restaurant would stand out in any neighborhood, and Garfield Park is worth it. They're known for brunch, but don’t miss their renditions of fried chicken, po boys and shrimp and grits, all available at lunch and dinner. For all three meals, you’d be hard pressed to find better food at better prices. The service is top notch, but gratuities benefit the company’s mission to train and secure employment for Chicagoans stricken by homelessness and poverty. Go anytime for a truly memorable meal. Inspiration Kitchens is located at 3504 W. Lake St.
Play at Garfield Park Conservatory: Opened in 1908, Garfield Park Conservatory remains an oasis of flowers, ferns, succulents and so much more on the city’s West Side. Beautiful in summer, fall and spring, the space transports shivering folk to a faraway land through our oft grueling winters. Thanks in great part to the Park District’s extensive renovations in the '90s, interest in and attendance (free) of the conservatory has grown, as it now plays host to dozens of touted events throughout the year.
Garfield Park Conservatory is located at 300 N. Central Park Ave.
Shop at City Escape: Looking for a pretty pot to house the new succulent you were inspired to purchase post-conservatory? Count on City Escape for unusual garden accessories to accentuate the blossoms, herbs and other vegetal delights you’ll find at this spacious nursery that you likely won’t find at your neighborhood Home Depot. City Escape is located at 3022 W. Lake St.Kristine Sherred

Graceland Cemetery/By Kristine Sherred


Eat at Ba Le: Dozens of excellent restaurants, from Southern to Belgian, Vietnamese to progressive American, call Uptown home. But for the purposes of this visit, Ba Le takes the cake with their easy to eat and easier to enjoy bahn mi in almost two dozen varieties. Their new location opened up space for French pastries to complement their bread program, meaning hungry customers can relish a divine three-course meal for under $20.Ba Le is located at 5014 N. Broadway St.
Shop at Broadway Supermarket: While on this Northside Asian expedition, stop at one of the area’s specialty markets, equipped with everything from fish, dried meat, fresh rice noodles and cans of coconut milk that will hurt your wallet significantly less than other grocery stores. Stock up on bundles of soba noodles for quick weeknight pasta dishes spiked with fish sauce, rice vinegar, lime and cilantro—making pad thai is easier than you think. Broadway Supermarket is located at 4879 N. Broadway St.
Visit Graceland Cemetery: Of course Montrose Beach might win Chicago’s finest in summer months, but when the breeze hits just a little too hard, head slightly southwest to experience true Chicago history. Established in 1860 by a prominent lawyer, Thomas Bryan, and supported by wealthy locals including our first mayor, William Ogden, the cemetery was and still is an oasis of architectural and landscape beauty. Our most beloved architects lay to rest here too: Louis Sullivan, John Root, Daniel Burnham, and Mies van der Rohe, among others, in addition to dozens of Chicagoans whose names one might recognize from street names galore. Graceland Cemetery is located at 4001 N. Clark St.
Drink at The Green Mill: No visit to Uptown would be complete without a session at the venerable jazz lounge. From the iconic sign to the unchanged decor, history and tradition live inside these walls (and in its underground tunnels), modeled after the '40s-era Uptown House in Harlem. Lesser known fact: The bar is open at noon every day and doesn’t charge a cover unless there’s music. But let there be music! The Green Mill is located at 4802 N. Broadway St.
Kristine Sherred

By Jessica Mlinaric

Humboldt Park
Eat at Nellie’s: No one should pass through Humboldt Park without sampling Nellie’s coconut oatmeal. Diners line up on Paseo Boricua to enjoy the cinnamon-sprinkled, velvety avena de coco, hearty breakfast buffet, and other authentic Puerto Rican breakfast and lunch fare. While trendy options continue to pop-up nearby, Nellie’s offers an unfussy setting where the omelets contain maduros and your coffee is always full. Nellie’s is located at 2458 W. Division St.
Play at the National Museum of Puerto Rican Arts and Culture: There are plenty of opportunities for play in Humboldt Park including fishing in the lagoon, lounging by the inland beach, or hitting the bag in the field house's indoor boxing gym. The park even includes a free art museum, America's only museum dedicated to Puerto Rican arts and history. Exhibits explore topics of Puerto Rican culture and community, ranging from faith to Chicago artists examining what it means to say "That's Puerto Rican." The small collection is housed in a Chicago landmark, a former stables that used to include landscape architect Jens Jensen's office and Humboldt Park's oldest surviving structure. The National Museum of Puerto Rican Arts and Culture is located at 3015 W. Division St.
Shop at Humboldt House: If you're on the hunt for vintage finds to adorn your modern pad pay a visit to Claire Tibbs and company. The store is home to stylish retro furniture and eclectic accessories that range from Turkish-sourced rugs to jewelry and soaps from Chicago artisans. Humboldt House even sells cleansing sage bundles for those who really want to revamp their space. Humboldt House is located at e1045 N. California Ave.
Drink at California Clipper: Longtime patrons of this Humboldt dive, which has been operating as a bar since 1937, wrung their hands when Brendan Sodikoff announced his intention to reboot the space. Thankfully, a blood-red glow of lights still fills the room, country western artists continue to take the stage, and most cocktails on the Clipper's extensive list remain $10 and under. Cheers to a Chicago classic. California Clipper is located at 1045 N. California Ave.
Jessica Mlinaric

At Nellie's. By Jessica Mlinaric

South Loop

Eat at Mercat a la planxa:There are tapas restaurants, and then there’s Mercat, whose authentic Catalan-inspired cocktails and shared cuisine will make you not only feel like you’re on a staycation but a real Barcelona vacation. Many come here for the whole roasted suckling pig (call 72 hours in advance) but for the squeamish like me, there’s a whole menu of cured meats, cheeses and fresh seafood including my favorite pulpo con patatas (Spanish octopus with potato and smoked paprika). A good bet is the multi-course brunch and bloody mary bar. Mercat a la planxa is located at 638 S. Michigan Ave.
Shop at Sandmeyer's Bookstore: The new Roosevelt Collection has brought a monolithic presence of big box stores like H&M, lululemon and The Container Store for residents in the post-downtown zone, but you’ll actually be doing more good for the community shopping at local places like Sandmeyer's Bookstore. The mom-and-pop bookseller is nestled in a beautiful historical building in the South Loop on Printer's Row. They appreciate loyalty—for just $10, you can get a member card for 10 percent off your purchases.
Sandmeyer's Bookstore is located at 714 S. Dearborn St.
Play at Blues Heaven Foundation: As we await a complete revitalized entertainment district in the old Motor Row, there’s a special place you can visit now that was once the home of Chess Records, where the magic happened for blues artists like Willie Dixon, Chuck Berry and Bo Diddley. Even the Rolling Stones once famously recorded here. The landmark building now houses nostalgic memorabilia and offers tours from Dixon’s grandson. Cap it off with a trip over to nearby Buddy Guy’s Legends for the full blues effect. Blues Heaven Foundation is located at 2120 S. Michigan Ave.Selena Fragassi and Rachel Cromidas

Maria's Packaged Goods and Community Bar (Image Credit: Eric Allix Rogers)


Eat at Pleasant House Bakery: (Updated May 2017: Pleasant House has moved a few blocks north since we wrote this list, but we think it's still well worth the trek during your Bridgeport staycation.) This adorable café specializes in Royal Pies. Handmade with savory fillings like kale and mushroom, steak and ale or chicken balti, these pies are always made with fresh ingredients and despite their moderate size, are always fillings. Pair one with a scotch egg and a side of mint peas to round out your distinctly British meal. Pleasant House Bakery is located at 2119 S. Halsted St. #1
Frolic at Palmisano Park: Pick a sunny day and head over to Palmisano Park, climb up the hill and get an amazing view of the city skyline. Other than a great vantage point, this park offers environmentally-sustainable designs, from recycled timber boardwalks overlooking a quarry pond to a crushed limestone running path. Take a walk on one of the trails, fish in the stocked logon or stop and take a photo with one of the many Buddha Head Sculptures on the top of the hill. Formerly known as the Strean’s Quarry, this park, which opened in 2009, is a nice green oasis and a quiet escape from nearby Halsted Street. Palmisano Park is located at 2700 S. Halsted St.
Play at The Co-Prosperity Sphere: While The Cell for a Sox game might seem like the obvious choice of where to hang out in Bridgeport, instead take a walk over to Morgan Street for an event at The Co-Prosperity Sphere. The Sphere hosts numerous gallery and cultural events throughout the year highlighting the neighborhood as a growing artist community. A peak at their latest events calendar shows live lit, underground comedy and contemporary art discussions taking place in their newly designed 5,000 square foot space. The venue also now serves as the home of Lumpen Radio, a new low-power FM radio station providing music and commentary on local Chicago issues, solidifying the space as a hotbed for homegrown culture on the South Side. The Co-Prosperity Sphere is located at 3219-21 S. Morgan St.Gina Provenzano


Eat at Wilde Bar & Restaurant: Anything that has to do with Oscar Wilde, we are game, especially this neighborhood Irish bar and restaurant. Not only is the food pretty great—fish & chips, lobster mac & cheese, chicken curry, shepherd’s pie and baked French onion soup being just some of the standouts—there’s also a pretty hefty drink list that includes of course whiskey and scotch, wine and beer flights and beer cocktails (with several local purveyors on draft). The ambiance is top notch too with cozy leather booths, old-school Brunswick bars and a library with fireplace for your wintertime staycation needs because that’s happening soon. Wilde Bar & Restaurant is located at 3130 N. Broadway
Shop at Belmont Army: “Army Strong” could also be the motto of this long-beloved indie fashion outpost that carries vintage military treasures (bomber jackets, combat boots) alongside designer shoes and skateboard gear. Several years back, the urban ‘department’ store got a complete overhaul and is now housed in a fancy glass structure with five floors of goods also including vintage and thrift shop apparel and men’s and women’s modern-day fashion. Not only is the selection good here, but so are the price points. Belmont Army is located at 855 W. Belmont Ave.
Play at Brew & View: When The Vic Theatre isn’t hosting concerts, it has a second face as a movie theatre with the long-running ‘Brew & View’ nights. Featured films run the gamut from second and third run hits to underground flicks and cult classics and are just $5 to get in. The best part is the venue’s bars are all open (the brew part of this series) so you can get toasted and not care that dinosaurs are taking over in “Jurassic World,” coming later this month. Get the full schedule at The Vic is located at 3145 N. Sheffield Ave.Selena Fragassi

Photo credit: Patrick Goff


Eat at Big Jones: Oh, the places you’ll brunch if you take your staycation in Andersonville. My top pick for brunch in this far North Side neighborhood is none other than Big Jones, a delightful spot that features coastal Southern cuisine. You could make a (very sugary) meal out of their griddlecakes and popovers alone. Big Jones is located at 5347. N Clark St.
Shop at Women and Children First: Andersonville’s Clark Street is home to a handful of my favorite speciality shops and antique furniture stores, including Gethsemane Garden Center and the greeting card and framing shop Foursided. But the number one place to get lost in on lazy afternoon stacyation is Women and Children First Bookstore. Browse their carefully curated selection of bestsellers, local authors and staff picks. Women and Children First is located at 5233 N. Clark St.
Watch The Neo-Futurists: Cap off a stellar day in Andersonville with a late-night showing of The Neo-Futurists’ Infinite Wrench. This new iteration of their long-running experimental theater show is not to be missed, and no two shows are exactly alike. The Neo-Futurarium also plays host to a number of well-received theater runs throughout the year. The Neo-Futurarium is located at 5153 N. Ashland Ave.Rachel Cromidas


Eat at The Lucky Platter: While everyone has been flocking to the lakefront community to test drive a swarm of trendy epicurean entrants—among them Boltwood (from ex-Publican chef Brian Huston) and Amy Morton’s Found Kitchen + Social House—we still find the best dishes at The Lucky Platter, serving “funkalicious post-Hippy eclectic world cuisine.” Each meal starts with fresh cornbread and a distracting look at the dizzying amount of weird paintings and tin art fixtures before devouring comfort dishes like Yankee Pot Roast, Tandoori Chicken Sandwich and a side of fried green tomatoes. It’s college town dining at its finest. The Lucky Platter is located at 514 Main St.
Shop at The Mexican Shop: There’s nothing particularly from Mexico at this boutique shop but the name hints at the owners’ predilection for traveling the world to bring back funky fare to sell to us boring stay-at-homers. Everything from jewelry to bohemian fashion and eclectic accessories is sold here, though it mostly caters to women. Just be sure to check to make sure the store is open and ‘in season’ as the owners do close up from time to time to go to market. The Mexican Shop is located at 801 Dempster St.
Play at SPACE: One of the area’s best listening rooms, the intimate concert venue caters to folk, rock, blues and alt country fans. SPACE is located at 1245 Chicago Ave.Selena Fragassi
(Editors note: We know Evanston is no Chicago neighborhood, technically, but it's still a great place to explore on your staycation.)

Logan Square

Eat at Lula Café: There’s no shortage of acclaimed places to grab a bite in Logan Square, but this quintessential neighborhood spot has been a staple in the neighborhood long before the cocktail lounges and coffee shops called Milwaukee Avenue and Kedzie Boulevard home. Lula Café is located just off the square and specializes in simple and delicious farm to table fare. In addition to brunch and dinner, an affordable café menu is always offered with classic Lula dishes like their Beet Bruschetta and Ham and Raclette Panino­. Brunch regularly draws a crowd with their delicious house pastries, rotating Royale breakfast sandwich and Lox Plate. For an extra special evening, visit on Monday nights for their special Lula’s Farm Dinner with a multi-course menu and wine pairings. Lula Café is located at 2537 N Kedzie Ave.
Shop at Wolfbait & B-Girls: This small shop right off Logan is packed with fun, offbeat and unique items all crafted by local designers and artists. Owned and curated by native designers, Shirley Kienitz and Jenny Stadler, Wolfbait has fashion, home goods and beauty products you won’t find at your everyday corner shop. It’s a great spot for keepsakes, especially for those who want to show off a little local pride. CTA stop wall art, sweaters proudly proclaiming “Midwest is Best” and a wall of locally made jewelry greets you as you walk in the door. Need a quick card or present on your way to a party? Free wrapping is available so you’re gift ready as soon as you walk out the door. Wolfbait & B-Girls is located at 3131 W. Logan Blvd.
Play at The Fireside Bowl: While the Fireside used to be known more as a music venue for budding local and national artists in the late '90s and early 2000s, is now mostly back to its bowling roots. This is not a squeaky clean, modern bowling alley, but it has all the charm (or lack there of) and nostalgia of a good local dive. Other than plenty of lanes to chose from, there’s a fully stocked bar perfect for drowning the sorrows of that sub-100 game you just threw. Located a little east of the square on Fullerton Avenue, it’s a great location to start or end your night with perfecting your throw and upping your average.
The Fireside Bowl is located at 2648 W. Fullerton Ave.Gina Provenzano

Ukrainian Village

Eat at Briciola: It’s hard to believe one of the best Italian spots in the city is located unassumingly on Damen Avenue, but it’s true. Those who live in UKV have long known Briciola is the spot to grab a lovely outdoor patio seat and enjoy complimentary bruschetta, house-made mozzarella and fresh pasta dishes. Inside you’ll find a romantic, cozy and warm space with great service. Best of all, this place is BYO, so grab a bottle of wine on your way and save money on drinks so you have some extra cash to order a tiramisu and espresso to end your evening happy and full. Briciola is located at 937 N. Damen Ave.
Shop at Alcala’s Western Boots: Whether you need boots to ride, line dance or just look fashionable in Alcala’s Western Boots on Chicago Avenue is the place for quality leather footwear in the city. There’s huge variety of boots to choose from ranging in styles and price that the exceedingly patient and helpful staff will help you find the right boot for you. Alcala’s has been around since 1972 and has had the neighborhood completely evolve around it. In that time it’s become known far and wide as the most authentic place in Chicagoland for cowboy boots and accessories. So while you’re there, why not grab authentic western wear like belt buckles, hats and wrangler jeans to complete your look and feel like you’re in the West, instead of just west of Ashland. Alcala’s Western Boots is located at 1733 W. Chicago Ave.
Play at Happy Village: You might be in Ukrainian Village, but don’t expect to find a cocktail menu or wine list at this hidden gem. Cheap drinks, ample outdoor seating and a ping-pong table room where things can get completive make this bar a fun place to play while you’re in the hood. Tucked away from the hustle of Division Street on Wollcott Avenue, this low-lit but inviting dive is a great spot to spend a few hours day drinking on the patio catching up with friends or grabbing a beer and a shot at the bar. Happy Village is located at 1059 N. Wolcott Ave.Gina Provenzano

The interior of Gather.

Lincoln Square

Eat at Gather: There is no better place for a slightly fancy (after all, you're on a staycation!) but also not pretentious (you're on a damn staycation, not a trip to Venice) dinner in the square than Gather. The adorable space, the perfect patio and the to-die-for hamburger is enough to make this spot a must visit, and if you're in the market for brunch, get there right at 10 on Sunday because it fills up fast. Gather is located at 4539 N. Lincoln Avenue
Shop at Merz/Q Brothers: For years, Merz Apothecary, one of the best soap/bath products stores in the whole city, has been bringing visitors to the Square. Now, they've opened an adjunct—Q Brothers, a store just for men. The shaving section at Merz got so popular, they gave it (along with fragrances, soaps, and other manly products) its own store, and it's a gorgeous white-tiled replica of an old drugstore. One warning: they aren't open on Sunday.Merz Apothecary is located at 4716 N. Lincoln Avenue.
Play at Fountainhead: If you're looking for night-time fun, there's no better spot then Fountainhead. It's got the best whiskey list in the city, a beer list that's out of this world, great food by Cleetus Friedman, and a rooftop that can't be beat. Get some smoked hummus and a manhattan and sit out under the stars and then head next door to Fountainhead Market to buy some fancy single barrel bourbon to bring home. Fountainhead is located at 1970 W. Montrose Avenue. Anthony Todd

Lincoln Park

Eat at Athenian Room: Perhaps Lincoln Park isn't the first neighborhood a foodie thinks about, even if Alinea calls it home. But there are diverse offerings to suit all budgets and tastes. Neighborhood stalwart Athenian Room got a shot of publicity when mentioned by Tina Fey a couple years back, and for good reason. Try their lemony Chicken Kalamata with Greek fries (drenched in the same lemon and herbs as the chicken). If ethnic mash-ups are more your thing, Del Seoul offers Korean tacos and their kimchi topped take on poutine. If you're looking for higher end dining, head to the Belden-Stratford. This Parisian-inspired apartment building houses two notable dining options on its ground floor. French bistro Mon Ami Gabi offers staples like mussels in white wine, French onion soup, and steak frites. Across the lobby, Lettuce Entertain You's ambitious Intro brings in a new up-and-coming chef every couple months, with an entirely unique menu for each residency.
Window shop on Armitage Avenue: Armitage Avenue is known for its high-end boutiques, from trendy women's fashions to home decor to precious outfits for the moneyed class's toddlers. If you're looking for more mainstream shopping without the dreaded trip to a suburban mall, North Avenue continues to expand its offerings with the New City development soon joining the likes of Crate & Barrel, West Elm, REI and the Apple Store.
Drink at Barrelhouse Flat: Despite its Trixie & Chad reputation, one can find some more interesting paces to grab a drink in Lincoln Park. Barrelhouse Flat offers swanky cocktails and a well-curated beer list, while the J. Parker offers breathtaking skyline views from its rootop above Lincoln Park. The recently re-opened Red Lion Pub is perhaps Chicago's most authentic British pub with a menu of kidney pie and fish & chips to go along with pints of the Isles' best brews.
Frolic in Lincoln Park: Lincoln Park's lakefront is an oasis in the city, with outdoor activities for all ages. North Avenue beach is the city's most popular stretch of sand and an awesome place for some beach volleyball. Lincoln Park boasts a free zoo. The Green City Market brings farmers from across the Midwest to Lincoln Park every Wednesday and Saturday. Caldwell Lily Pond offers a tranquil sanctuary that feels miles away from the bustle of Chicago. And he Notebaert Nature Museum‎ provides a connection to nature that one too often overlooks in a big city. —Benjy Lipsman


Shop and Play at The National Museum of Mexican Art: The museum and its fantastic store are one of the city’s hidden gems. The shop is full of art, jewelry and other unique, handmade items selected by staff during regular shopping trips to Mexico. Not only is museum admission free, there are always a multitude of events including concerts and special exhibits going on here. The museum has more than 7,000 works of art in its permanent collection, making it one of the U.S.’s largest Mexican art collections. The National Museum of Mexican Art is located at 1858 W. 19th St.
Thalia Hall: Thalia Hall is one of the newest venues on the Chicago music scene and, at the same time, it's one of the oldest. The building was built in 1892 and modeled after an opera house in Prague. It was closed for many years until owners Bruce Finkelman and Craig Golden brought it back to life in 2013. A wide variety of acts play at Thalia Hall including upcoming shows by Destroyer, the Maccabees, the Drive-By Truckers, Houndmouth and Deerhunter. Thalia Hall is located at 1807 S. Allport St.
Second Fridays Gallery Night: On the second Friday evening of each month, more than 30 art galleries and studios in Pilsen open their doors for Second Fridays Gallery Night. Visitors can poke around galleries for free, see some intriguing art, meet some of the artists and buy works of art. Stop by the information center to start your walk. The Chicago Arts District and Second Fridays Gallery Night information center is located at 1821 S. Halsted St. Kate Shepherd


Play at the Beverly Arts Center: This neighborhood staple is a movie theater, art gallery, concert venue and fine arts school. It offers classes for all ages ranging from ballet to sculpture to improv comedy to guitar. There are always art exhibits going on in the gallery and a lot of special events including author afternoons with visiting local authors.
The Beverly Art Center is located at 2407 W. 1111th St.
Eat at the Beverly Bakery and Cafe: Coffee lovers unite, the friendly neighborhood joint features more than 20 coffees from around the world roasted in the café in small batches. If you love the coffee, you can take it home or even order more on their website. If you go, don’t skip the fresh-made pastries and full breakfast menu which has a big following. The Beverly Bakery and Cafe is located at 10528 S. Western Ave.
Shop at Beverly Records: This is the spot for vinyl buffs. If you can’t find a rare record anywhere else, you might be able to get it here. The store specializes in rare vinyl records including some signed records. There’s a wide selection and helpful staff. Beverly Records is located at 11612 S. Western Ave. Kate Shepherd


Shop at Gallery Guichard: Treat yourself to some original art from this contemporary gallery specializing in works by artists from the African Diaspora. With a wide selection of paintings, sculptures and ceramics, there is something for everyone and all price ranges. Co-owners Andre and Frances Guichard are happy to help buyers find the right art and to answer any questions. Gallery Guichard Gallery Guichard is located at 436 E. 47th St.
Eat at Ain’t She Sweet Café: This neighborhood favorite is known for its fantastic, flavorful sandwiches (jerk chicken wrap is a cult favorite), soups, salads and smoothies. It’s a very welcoming place with local art covering the walls and great service. Make sure you grab some of the free cucumber water. Ain’t She Sweet Café is located at 526 E. 43rd St.
Play at Jokes and Notes: Owner Mary Lindsey was named one of Crain’s top entrepreneurs for the success of this 150-seat comedy club. A mix of nationally-known comedians (Oscar winner Mo’Nique has performed here) and great local acts take the stage on a regular basis. Grab a drink at the full bar and enjoy a fun and relaxing night full of laughs. Jokes and Notes is located at 4641 South King Dr. Kate Shepherd


Play at Red Pepper’s Lounge: A sports bar in front and a music venue in back, Red Peppers is a must-see for jazz enthusiasts. They’re best known for jazz but also host regular comedy shows. Cajun food is the specialty, so make sure you order some after you enjoy a drink. Red Pepper’s is located at 428 E. 87th St.
Eat at Lem's Bar-B-Q: Lem's is the place for true barbecue fans and those who want to take a bite out of Chicago's barbecue history. As we wrote in 2015 when "Lem," a.k.a James Lemons, passed away, the rib joint has been an icon of the South Side since it opened in 1954, with its aquarium smoker and "revolving bulletproof plexiglass Lazy Susan for handing over money and dispensing ribs", according to the Sun-Times.Lem's is located at 311 E. 75th St.
Shop at Fragrance Island: Perfume junkies and bargain hunters will go nuts at the storefront for online wholesaler Fragrance Island. They have hundreds of body oils, lotions, soap and incense in stock. With such a wide selection, you’ll never get tired of trying new scents. Fragrance Island is located at 641 E. 79th St.
Play at Rainbow Beach Park: Although the beach is located a few blocks east of Chatham, it’s definitely worth checking out while in the area. Rainbow Beach is an exceptionally beautiful, nearly 61-acre beach and park with an incredible view of the downtown skyline. Stop by the playground with kids or play a game on the handball courts. Rainbow Beach Park is located at 2873 E. 75th St. Kate Shepherd

Photo courtesy of A10

Hyde Park

By Day: By day in Hyde Park, we recommend taking a Divvy out to Promontory Point and taking in the beauty of Chicago’s lakefront and skyline from this go-to South Side picnic spot. Hit up local favorites such as grocery store Open Produce and the Medici Bakery and make a picnic feast of it. And for a more active staycation, ride that bike south along the lakefront to the historic South Shore Cultural Center for an even more scenic excursion. Promontory Point is located at 5491 S. South Shore Dr.
Eat at A10: A focal point in Hyde Park’s growing restaurant scene is A10 a project from Chef Matthias Merges of Billy Sunday and Yusho fame. A10 features French and Italian fare. A10 is located at 1462 E. 53rd St.
A Night At Court Theatre: Hyde Park’s Court Theatre may fly a bit under the tourist radar, but it’s world-renowned in theater circles for good reason. Playwright August Wilson’s Gem of the Oceanstarts next week. Court Theatre is located at 5535 S. Ellis Ave.Rachel Cromidas