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The Best Chicago Date Ideas, According To Our Readers & Staff

By Staff in Arts & Entertainment on Mar 15, 2017 5:51PM

Earlier this year, we asked readers to tell us their dating secrets—specifically, what places around Chicago make for excellent date night (or date day) spots, whether it's your first date or your 1,000th. Readers and staffers at Chicagoist gave us over a dozen examples of favorite date spots and Chicago date ideas. Please have a look, and let us know if we missed one of your favorite date spots! We can say that for us, if it involves exploring Chicago, having fun and getting to know your date better in the process, then it's a win.

And if you're looking for more ideas, check out our list of some of the best first dates spots in town.

Photo credit: Dan Gaken

Adler After Dark

Adler After Dark makes date night both romantic and educational. Not only is the entire museum available for exploring to patrons after dark, but it also still plays its regular sky shows in its three theaters—along with the special bonuses of live music, drinks and hors d'oervres. If you get lucky and go on a day with clear skies, the Adler staff might also help you peek at whatever celestial bodies happen to be overhead via telescope. And for those who like to get fancy on their night out: Every month has a different theme with a suggested dress code—upcoming events include "Geek Chic" and "Planetary Prom"...interpret them as you will!
The Adler Planetarium is located at Museum Campus, 1300 S. Lake Shore Dr.

The Mary Pickford. Photo courtesy of Scofflaw.


Reader Jenna Kowalczyk had this to say about her favorite date spot, Scofflaw:

About two years ago my boyfriend and I planned to spend our first Valentine's Day together doing date-y things, even though we're not usually into the whole V-day thing. We ended up grabbing dinner at 90 Miles, which was great by itself, but we didn't exactly want the night to end. We decided to hit up Scofflaw, a gin cocktail bar in Logan Square, for a "couple" cocktails. We nabbed two comfy chairs around a small table in the side room and shared a couple...or few $8 gin cocktails. Then around midnight the waiter came out with some fresh baked cookies(!) and then at last call our waiter talked us into a PBR and a shot of Malort. Can't pass that up. Needless to say—we were feeling pretty fantastic when we left.

To this day I don't think I've had more fun on Valentine's day...or date. Scofflaw continues to be one of our favorite date spots.

Scofflaw is located at 3201 W. Armitage Ave.

Drawing Room (Photos by Clayton Hauck, courtesy Land & Sea Dept)

The Drawing Room at the Chicago Athletic Association Hotel

The Drawing Room at the Chicago Athletic Association is our first date secret weapon. Picture this: A moody sitting room with working fireplaces and cozy leather seats that serves coffee from Metropolis, and cocktails and food from the award-winning Land and Sea Dept. restaurant group. It's right in the Loop, it's open late, there's free wi-fi, should you need it, and no one will ever hassle you if you linger at your table or don't feel like ordering more than one item here and there, because it doubles as the Chicago Athletic Association's hotel lobby. We love the Drawing Room because it strikes the perfect balance between grabbing a casual drink (and ducking out, if the date blows) and starting an adventure; you can stay for a while, but there are so many directions you can take the date in once you've settled in—you can explore the historic building and admire its recent restoration; you can try your luck getting a seat outside at Cindy's rooftop bar, with its stunning views of Millennium Park and Lake Michigan; you can play a round of pool, shuffleboard or bocci in the nearby Game Room; or go the low-brow route and grab Shake Shack on the floor below. Seriously, there are at least five solid date night plans that begin with the CAA's Drawing Room. Check it out, and invite us.
The Chicago Athletic Association is located at 12 S. Michigan Ave.

The new donuts at Ipsento. Photo viaIpsento’s Facebook Page

Ipsento 606

As a date night spot, Ipsento 606 is as gorgeous as it is versatile. If you're just meeting for coffee, that's great, because Ipsento is known for its excellent brews—and even better if you're hoping your coffee date will lead to an afternoon bike ride, because Ipsento 606 opens out right onto one of The 606's ground-level parks. As the sun goes down, it also becomes a great spot to meet for drinks and light dinner fare—but you must promise us you'll order the sweet potato fries. Dinner and drinks could lead to dessert; Ipsento has fresh pastries behind the counter and hot chocolate. Or even, sweeter, it could lead to a romantic walk along The 606.
Ipsento is located at 1813 N. Milwaukee Ave.

Photo via Beermiscuous


Reader Krishna Patel explains to us why every date night has to be special:

I do not get to have the luxury of date night every weekend. And no, it is not because I am single. My date nights have to be planned through plane tickets and PTO days. My lovely boyfriend and I have been doing long distance for 2 1/2 years. While he is getting his Ph.D. in New York, I am working on graduate classes here in Chicago while sustaining a full-time job. Let me tell you, long distance is hard, but worth it. So when he ventures out to Chicago, we try and hit up the best hot spots for us. Whether it is relaxing on the rooftop at JParker or a night out at Public House, Chicago has got us covered. ... If you just want to play some cards, connect four and sit by a fire, Beermiscuous is the place for you, all while enjoying flights of different beers.

Beermiscuous is located at 2812 N. Lincoln Ave.

Rosehill Cemetery via Wikimedia Commons

Rosehill Cemetery Mausoleum

Reader Charlie Cohen tells us why you might want to consider taking your date to a cemetery:

One of the best dates I've ever been on was to the Rosehill Cemetery Mausoleum. I'm not a spooky, halloween-y, Say Cheese and Die type by any stretch. I found out about the mausoleum when a major bathroom emergency forced me to pull off of Western Avene into the cemetery, praying there was a public toilet somewhere on the premises. While searching for the bathroom I walked through the first floor of the mausoleum. I was absolutely blown away by the marble, the light, the design of the building itself. I had to come back.

Freeness was the most attractive quality of this date idea (This was a time in my life where dining al fresco meant Chipotle in my concrete backyard next to the train tracks) followed by the privacy and unbelievable quiet of the place. We strolled and talked and gazed for two hours without seeing a single other person.

The top floor are the marble and granite shelf internments with windows at the end each aisle that look onto the lush grounds of the cemetery. The lower floors are these private cells each with their own custom stained glass windows and designs. This is where you find the big Chicago names: Shedd, Florsheim, Mayer, Schwinn and a bunch of other guys with streets named after them.

Even though you are just a few feet away from dead bodies, the feeling of being there is ethereal and serene rather than macabre. The combination between the history, the beauty and the feeling of intimacy in an unfamiliar place really brought out a shared interest between us that neither knew was there. It also broke us out of our routine of smoking weed and watching Gossip Girl in bed and started our quest exploring unfamiliar parts of Chicago which almost 4 years later we are still on.

Rosehill Cemetery Mausoleum is located at 5800 N. Ravenswood Ave.

Water Taxi, via Chicagoist Flickr Pool User Stephanie Barto

From London House to Chinatown
Reader Joe Koecher walks us through his favorite, day-long date that takes you from late-afternoon Cocktails at the London House rooftop downtown to the Water Taxi down to Chinatown:

I share this all the time with friends and its quite unique and a winner every time.

START: Late afternoon cocktail on the top of London House.
Skip the crowds and head up there early to grab a seat at the bar for a pre-evening cocktail while enjoying the view.

NEXT: head below to Michigan Avenue and grab a Chicago Water Taxi to Chinatown. Its the best $6 bucks you'll ever spend on a date. Most people are not even aware that you can hop on the river taxi and it drops you off in Chinatown.

From there it's a five minute walk to the center of Chinatown and any number of Chinese restaurants. Take your pick! I enjoy the lovely Chi Cafe.

FINALLY: take the river taxi back into the city and get off at one of the new areas of the Riverwalk for an evening stroll with a night cap at Tiny Hat.

London House is located at 85 E. Upper Wacker Dr. and Chi Cafe is at 2160 S. Archer Ave.

Photo courtesy of 3 Arts Club Cafe

3 Arts Club Café at Restoration Hardware

If your idea of an awesome date involves sharing a cheese plate besides sparkling chandeliers and an indoor garden fountain, then browsing five-plus floors of fancy furniture with a cocktail or coffee in hand, then you must visit the 3 Arts Club Café. For the uninitiated: this charming sit down lunch and drinks spot is located inside a historic Gold Coast building that is now a flagship Restoration Hardware store. And if that sounds like it really is not your cup of tea, bear with us: If you time your visit right, you can bypass the café and head up to a gorgeous, little-known rooftop seating area to watch the sun set over River North. It's technically part of the Restoration Hardware and not a dining area, so you can expect to take in some excellent city views without the long lines and pricey dining bills of other rooftop spots.

The 3 Arts Club Cafe is located at 1300 N. Dearborn St.

At the Promontory (Photos by Clayton Hauck courtesy of The Promontory)

The Promontory

The Promontory is a popular bar, restaurant and concert venue to put on your destination list, whether you can walk there from Hyde Park or are coming from out of town. Look up who's performing before you go or be surprised; sip on craft cocktails and enjoy a small plates menu with locally-sourced ingredients. And if you're date is going well, we recommend you make a pact to come back soon for brunch.

The Promontory is located at 5311 South Lake Park Ave West.

via Brooklyn Boulders

Brooklyn Boulders

The couple that belays together stays together, we always say. A day pass to Brooklyn Boulders in the West Loop, or any of the city's growing numbers of climbing gyms, for that matter, could make for a creative and fun afternoon date, whether it's date number two or date 200. Brooklyn Boulders has all the gear you need, and multiple bouldering courses tailored to complete beginners, so don't worry if you can't do a pull-up. Even the easiest routes are challenging enough to encourage teamwork, meaning you and your date can stick together and help each other figure out the best routes for making it up the wall. If you want a slightly more involved day of rock climbing, or you're dying to climb higher, plan on taking an introductory lesson so that you can belay each other on a climbing rope up some of Brooklyn Boulder's 50-foot walls.

Brookyln Boulders is located at 100 S. Morgan St.

2017-honkytonkribs.jpg Via Honky Tonk BBQ

Honky Tonk BBQ

If your date loves BBQ as much as we do, take them to Pilsen's award-winning Honky Tonk BBQ. This Western-style bar features delicious, authentic BBQ fare, live bluegrass or western music almost every night, lots of unique art, and house-made cocktails like The Lonely Presbyterian. We recommend ordering the pulled pork, brisket, corn muffins, "bacon candy" and seriously amazing banana pudding—and if that sounds like a lot of food, maybe you should grab a couple of friends and make it a double date?

Honky Tonk BBQ is located at 1800 S. Racine Ave.

Green City Market/Brunch at Cafe Brauer

One of the best ways to spend a Saturday morning, especially when the weather gets nicer, is this one-two punch of Chicago icons. First, head to Green City Market, the amazing farmer's market in Lincoln Park, and buy all the gorgeous local produce and meat that you can carry. Don't buy any prepared foods, though, because you've got brunch plans. Walk through the Farm in the Zoo (and maybe get a glimpse of some adorable baby goats and rabbits). Then, head across the South Pond to Cafe Brauer. After the renovation of the South Pond space, Cafe Brauer started serving a full service outdoor brunch menu, complete with cocktails. The food is solid, the prices are reasonable and the view literally cannot be beat, with a clear shot across the pond all the way to the skyline downtown. Our suggestion? Go around 9 a.m. to the Market and around 10 a.m. to brunch. —Anthony Todd
Cafe Brauer is located at 2021 N. Stockton Dr.

Winnemac Park, photo via Yelp

Wander the Prairies of Winnemac Park

Winnemac Park is, hands down, one of the nicest green spaces in the city, and lots of people have visited once or twice. What they might not know is that Winnemac Park also boasts one of the best prairie restoration projects in the city limits. Big chunks of the park have been restored to some version of native Illinois prairie, and paths allow visitors to become totally enveloped in the grasses, which by mid-summer are taller than the tallest visitor. It's especially fun at night, when you can listen to grasshoppers and crickets and, maybe, canoodle a little in private (shh). Afterwards, head to The Sixth or Bang Bang Pie and Biscuits—both an easy walk from the park. —Anthony Todd

Winnemac Park is located at 5100 N. Leavitt St.

Original Rainbow Cone / Facebook

Original Rainbow Cone

If your date doesn’t have room in his or her heart for this Beverly staple, you might want to rethink having room in your heart for them. A South Side institution for nearly a century, sure it’s a sucker cut, but sometimes there’s a reason the choice is obvious. If you're looking for the sweetest during the warmer months, there’s no better than the deliriously multi-hued and delicious Original Rainbow Cone combo—or as we like to call it, the Amazing Technicolor Dream Cone. The layers of chocolate, strawberry, Palmer House, pistachio and orange sherbet are true love.
Original Rainbow Cone is located at 9233 S. Western Avenue


Stay in and watch Easy on Netflix

Sure, we promised you date ideas to get you out there, exploring your city and its cultural and culinary offerings. But sometimes there's several inches of snow on the ground and you just want to stay in. We know how it goes. Which is why our final favorite date night suggestion requires nothing but a wifi connection and a Netflix login. Easy is a lighthearted but thoughtful show, set entirely in Chicago, that explores big themes—monogamy, trust, art, authorship, how to start a brewery with your buddies out of a garage... The show will have you laughing and cringing along with the characters as they navigate their Chicago love lives with and without success, and it also offers some steamier scenes, too (Spoiler: Orlando Bloom is a fitness instructor, and he hooks up with Kate Micucci and Malin Akerman. Skip ahead to this episode, if you must).