Saturday Series over 6 years ago by Liz Adams

The Best Chicago Date Ideas

making our marriage a priority after having a baby with express

Today we’re responding to a reader request from our Facebook group for the best Chicago date ideas! Because let’s be honest, we could all use a little inspiration every now and then—there’s a time and a place for everything, but you don’t always want to end up at another sports bar or find yourself ordering Piece pizza and watching movies on the couch for the third Friday that month. I crowdsourced ideas from my most trusted girlfriends, who all offered up fabulous ideas for everything from a first date to a five-year anniversary—I couldn’t agree with their suggestions more! As for when I asked my own boyfriend what he likes to do together in Chicago, he said, “going out and then coming home to eat ice cream.” There’s a reason we get along. But I digress…without further ado, here’s the giant list of Truly Great Chicago Date Ideas:

City Winery along the river
The Signature Room to watch the sunset
The Aviary for the adventurous at heart
The Whistler 
The Robey 
ACE Hotel
The Drawing Room at the Chicago Athletic Association 
EZ Inn for some hip vibes 
Guthrie’s (plenty of board games to ease first-date tension!)
Half Acre Taproom 
Revolution Brewing 

City Winery: one of Liz Adam's favorite date night spots in Chicago!

Asado Coffee Pickwick Lane 
The Allis Cafe at Soho House 
Heritage General Store 
Stumptown in the West Loop 
Purple Llama 
Dark Matter 
Ipsento in Wicker Park 
CC Ferns 

Asado Coffee: one of Liz Adam's favorite places for a coffee date in Chicago

Night out:
Coalfire Pizza on Southport (see a movie at Music Box, after) 
Tango Sur, also on Southport, plus Jeni’s for dessert 
Mott St. (one of my favorites) 
Cho Sun Ok for Korean bbq (good for double dates!) 
Longman & Eagle 
Lula Cafe (I love their brunch, too!) 
– Byob at JJ Thai in Ukranian Village followed by drinks at Forbidden Root
Nha Hang Viet Nam on Argyle for authentic Vietnamese food 
– Dinner at Dusek’s, drinks at Punch House then a show at Thalia Hall

Dusek's: a great Chicago date night spot!

When you’re feeling fancy:
Nico Osteria 
The Publican 
Steak 48 
Gibson’s Italia
La Sirena Clandestina 

Gibson's Italia in Chicago...a great date location for when you're feeling a little fancy!

Just for fun:
– Catch a comedy show at The Second City (the Improvised Shakespeare Company at iO is always fun, too) 
Paper Machete at the Green Mill (a weekly, free live magazine every Saturday at 3 pm)
– Cooking classes at The Chopping Block 
Chicago Symphony Orchestra
Restoration Hardware (lite bites + dream home shopping downstairs, closing out with a drink on the roof)  
– Salsa dancing at Latin Rhythms (an awesome loft space in the West Loop, check out their social nights every Saturday)
Adler After Dark 
Jazzin’ at the Shed 
Aire Ancient Baths (from everything I’ve heard this is an amazing experience!) 

3 Arts Cafe at Restoration Hardware in Chicago...a surprisingly good first date spot!

– Ice-skating at Wrigley or Millenium Park 
– Curling and drinks at Kaiser Tiger 
Scofflaw for the fireplace and free cookies at midnight 
Lost Lake (because there’s nothing like tiki drinks and banana dolphins in February…check out posters at Galerie F while you’re in the area) 
– Explore the Art Institute (free on Thursdays for Chicago residents, free on the first Saturday of every month for Bank of America cardholders), then get drinks at Cindy’s 
– Soak up the warmth at Garfield Park Conservatory then take a quick uber over to Spinning J, an old-school soda fountain, and spend the afternoon exploring all the cool antique stores in Humboldt Park 

Ice Skating in Millenium Park is a romantic winter date night for Chicago couples!

– Bring a picnic to an outdoor movie (free!) in Millenium Park
– Breakfast/snacks at Bang Bang Pie and then walk the 606
Kayaking on the river (I’ve done this; it’s fun and gives you great views, but you’ll want to take a shower immediately after, haha) 
– If you’d prefer to avoid getting wet, rent a pontoon boat and charter your own romantic evening with friends
– Stroll through Lincoln Park zoo and take in the Chicago skyline views from the Nature Boardwalk 
Diversey Driving Range
– Take an Architectural Boat tour (I’m always surprised by how many people haven’t done this!) or tour the Rookery Building
Green City Farmer’s Market in Lincoln Park 
– Brunch outside at The Winchester 
– Spend a summer evening on the Sportsman’s Club patio 
– Pack an epic picnic and experience a concert at Ravinia

Green City Farmer's Market is one of Liz Adams' favorite summer activities in Chicago!

In the Western suburbs:
– Hinsdale: Cocktails and appetizers (we love the mussels and crispy kale!) at the bar at Vistro, sushi and lychee martinis at Nabuki
– Western Springs: Dinner and fancy cocktails at Vie, pasta and red wine at Davanti Enoteca
– LaGrange: Pasta and yummy pizzas at Lucca’s

What are some of your favorite dates in Chicago? Let us know and I’ll add them to the list! 

xo, Carolyn 
Images: 1 // 2 // 3 // 4 // 5 // 6 // 7 

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  1. For the Western burbs, I HAVE to add Antico Posto in Oakbrook and Blackberry Market in Glen Ellyn. So lovely!

    I love this list because it’s not loop-centric! Tango Sur is amazing, so going to second that. The list has given me SO many new ideas, for both dates with my love and my buddies!

  2. I too LOVE that this list is not loop specific. Would love to bookmadk all these ideas on a google map to save too… would be so convenient!

  3. My fiance and I met in Chicago and had our first date/he proposed at Longman and Eagle!! (Not the same date, to be clear–haha!) So many of these places carry so many beautiful memories, even though we don’t live in Chicago anymore. Spot on list.

  4. Always love the Chicago recs! If my husband and I ever make a trip up, I’ll definitely reference this list. If I’m coming to the city solo for a conference next month, where would you recommend? I’d love to hit some great spots, but don’t want to feel out of place if I’m by myself. I’ll be eating dinner on my own a couple times and will also have some time to kill during the day around my flight schedule. I’m not super savvy on the different areas of town, but I’ll be staying near River North based on a google map.

    1. So fun! I really like Beatrix, Goddess & the Baker and Left Coast Food and Juice in River North for a solo lunch (Beatrix is good for dinner, too). 3 Greens Market, Centennial, and Bernie’s Lunch and Supper Club are great/low-key, too! You’re pretty close to downtown, so I would definitely recommend checking out the river walk or the Art Institute/Cindy’s at the Chicago Athletic Association if you have some free time!