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:
Drinks:
– 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
– Hopleaf
Coffee:
– Asado Coffee Pickwick Lane
– The Allis Cafe at Soho House
– Floriole
– Heritage General Store
– Stumptown in the West Loop
– Purple Llama
– Dark Matter
– Ipsento in Wicker Park
– CC Ferns
Night out:
– Coalfire Pizza on Southport (see a movie at Music Box, after)
– Tango Sur, also on Southport, plus Jeni’s for dessert
– Avec
– Giant
– Kitsune
– 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
– Daebak
– Dinner at Dusek’s, drinks at Punch House then a show at Thalia Hall
When you’re feeling fancy:
– Nico Osteria
– The Publican
– Monteverde
– Steak 48
– Gibson’s Italia
– La Sirena Clandestina
– Bellemore
– Entente
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!)
Winter-specific:
– 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)
– ZooLights
– Christkindlmarket
– 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
Summer-specific:
– 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
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!