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17 Awesome Chicago Neighborhood Staycations

By Staff in Arts & Entertainment on Sep 3, 2015 8:00PM

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's last hurrah nigh 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 go-to vacation destinations like the Art Institute and Millennium Park out of the running.

Here's the premise we gave our staff: 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.

Garfield Park Conservatory/By Kristine Sherred

Garfield Park

Eat at Inspiration Kitchen: 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 urban re-mix: 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 places like urban re-mix, an upscale home furnishings consignment shop owned by a mom-and-son team. The store offers everything from elegant chandeliers and mirrors to tribal masks and unique antiques that you won’t find at the Z Gallerie down the street. Instead, the store aims to be a sustainable resource by recycling goods to new homes and has won awards from the Alliance for a Greener South Loop. urban re-mix is located at 1468 S. Michigan Ave.
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

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


Eat at Pleasant House Bakery: This adorable café right off of 31st Street 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. Other than pies, Pleasant House serves up a special every night of the week. Go Wednesday nights for house made banger sausages or Friday night for a traditional Fish and Chips entrée. This is a BYOB establishment which means you can place your order and head next door to Maria’s Packaged Goods for a beer or cocktail and have your food delivered right to your table. Pleasant House Bakery is located at 964 W. 31st St.
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 NeoFuturists: Cap off a stellar day in Andersonville with a late-night showing of The Neofuturists’ Too Much Light Makes The Baby Go Blind. This 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 exotic 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. They have booked everyone from Henry Rollins spoken word tours and blues great Johnny Winter in the past, while upcoming acts include Wanda Jackson (September 25), Geen Ween (October 1) and Bob Mould (October 11). 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.
Eat at Nuevo Leon: Nuevo Leon is a Pilsen classic and one of the most popular Mexican restaurants in Chicago for a reason. The food is reliably good and fresh. (handmade tortillas!) The portions are huge but the prices are very low. What you need to know if you go: they only accept cash and you might have to wait in line for a table. Nuevo Leon is located at 1515 W. 18th St.
Play at 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.
Play at 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 Original Soul Vegetarian: There’s a reason this vegan restaurant has been in business for 33 years. They’re well known for their wonderful veggie gyros, BBQ twist sandwiches and weekend breakfasts. Whole Foods even carries some of their classic foods. Grab a drink at the juice bar while you’re there. Original Soul Vegetarian is located at 203 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