Being an awesome date isn't always easy.
Do you go for plans that are tried and true or try to impress with something more adventurous? There's so much to do in Chicago. How do you funnel it all down into one perfect evening? Take the pressure off yourself the next time it's your turn to plan by scanning our suggestions of the best date ideas in the city. We think there's a little something for everyone here. Just make sure we get an invite to the wedding!
Updated February 2025
Photo via Facebook/Steppenwolf Theatre Company
Chicago is home to amazing independent theaters and production companies all over the city producing accessible, enjoyable shows—even if you’re not the biggest theatre buff. Steppenwolf Theatre’s productions are always big wins with all audiences. Annoyance Theatre skirts the line between scripted and improvised plays, often with hilarious results. The historic Goodman Theatre has been a staple in Chicago’s not-for-profit theatre community for decades. Skip the screens the next time you’re in the mood for a movie night and reward yourselves with a live performance instead!
Photo via AIRE Ancient Baths
What says “I love you” more than a floating peacefully beside your special someone? The experiences at AIRE Ancient Baths are as diverse as they are extravagant. If you’re looking for the ultimate premium date idea, you might have just found it.
PHOTO: KATER JAYNE PHOTOGRAPHY
Not like that! Chicago is home to some of the weirdest, coolest spots you can imagine and you can plan an unforgettable (in a good way) date by visiting one of them. Spend your Friday night turtle racing, stroll through Chicago’s largest collection of leatherwear, and more!
Photo via Facebook/Garfield Park Conservatory
There’s so much more to do at the Garfield Park Conservatory and Chicago Botanic Garden than just walking around taking in the beautiful greenery–though that’s not a bad idea. Take a cooking class, brush up on your gardening skills or get into some couples yoga.
Photo via Facebook/WhirlyBall
Yes, it’s strange. Yes, it’s kind of silly. However, WhirlyBall (Chicago’s unique mix of bumper cars, basketball and lacrosse) has been a classic date activity amongst locals for years. Show off your competitive edge while still keeping things fun. How can they not be when you’re doing something this ridiculous? Pro tip: Whirly Ball is even better for group dates. The more players on the court, the better the matches will be.
Photo via Facebook/Firecakes
You can never go wrong with an old-fashioned date over some coffee and donuts, especially if your sweetheart has a sweet tooth. Just promise us you'll skip the gas station donuts, and take your date to one of the numerous high-quality bakeries around the city instead. We also recommend Do-Rite Donuts and Donut Vault. They’ll thank you, and so will your stomach.
Photo via Facebook/Eataly
It might seem odd to plan a date at a grocery store of sorts, but Eataly’s multiple restaurants (and regularly scheduled special events) will allow you to introduce delicious pizzas, pasta, cheese and more into your love life. Need a smooth way to keep your date committed to further hangs? Suggest buying a bottle of wine to share on the couch after dinner or buying the ingredients needed to make your own Italian feast at home for your next date.
Photo via Facebook/Headquarters Beercade
Save Up Your Quarters & Hit The Arcade
Quit playing games with your heart and just play them with your date instead! Chicago’s got lots of great arcade bars, like Headquarters and Emporium, that make for a unique and entertaining date beyond the usual drinks at a bar scenario.
Photo via Facebook/The Plant
Truly one of Chicago's coolest destinations, The Plant is a local business incubator that focuses on energy efficiency! Located in the Back Of The Yards neighborhood, you can spend a day touring the building or Whiner Beer Company's brewery and taproom. (Learn a little something about Whiner's hard kombucha process too.) Shop locally made goods at the The Turtle Stop. Visit on a Sunday for "Vegan Paradise"—a vegan farmers market thrown by Chicago Vegan Test Kitchen. Pick up delicious goods from businesses that call The Plant home—like Bungalow Bread, Great American Cheese Collection and more. Visit the Packingtown Museum to learn about the industrial history and cultural heritage of Chicago’s Union Stock Yard and surrounding neighborhoods.
There's seriously so much to do and see at this hidden gem!
Photo via Facebook/Davis Theater
The recently remodeled Davis Theater in Lincoln Square is a super cute alternative to the classic “dinner and a movie” date night. The Davis offers a neighborhood hangout atmosphere much preferable to the massive cineplexes downtown. And, if things are going well, you can spill over into the cool and casual adjacent Carbon Arc Bar for food and drinks after the flick.
Of course, we always champion any of Chicago’s independent movie theaters like The Music Box, Logan Theater and Harper Theater.
Photo via Facebook/Lincoln Park Zoo
There are two main reasons Lincoln Park Zoo should be at the top of your list of date ideas. 1. It’s free, so you can save your money and spoil your date later. 2. Who needs a wingman when you got cute animals to help woo your significant other?
Want to safari outside of the city? Brookfield Zoo is also an absolute gem.
Photo via Facebook/The Aviary
Be A Cocktail Connoisseur For The Night
Splurging at one of Chicago’s hottest cocktail bars is never a bad thing. Learn the true meaning of “mixology” at The Aviary. Indulge in the romantic atmosphere of Sweethearts Bar, catch the speakeasy vibe at Broken Shaker at Freehand Chicago. The Violet Hour also has "date night" written all over it.
Photo via Facebook/Uncommon Ground
Enjoy Dinner & A Show
...at the same damn time. Seated dinner shows at venues like Uncommon Ground and City Winery can satisfy both the foodie and music-loving sides of your personalities.
Photo via Facebook/Chicago Park District
Chicago’s certainly isn't short on parks. No matter what neighborhood or part of town you live in, you're bound to find a cute park, big or small, within walking distance—the perfect setting for an afternoon or evening picnic with bae.
Impress your special someone with insider knowledge of the best places to dine around town. Check out which restaurants made this year's list. Make sure you put your planning skills to use and book a reservation in advance.
Photo via Facebook/Sushi Suite
Book A Tasting Experience For Two
Speaking of fantastic dining experiences in Chicago, a tasting menu is a great way to explore new culinary boundaries with your partner. Sushi Suite (also known as Suite 202) is a speakeasy-style omakase restaurant located inside of one of Hotel Lincoln's second-floor rooms! Work your way through 17 courses of palate-pleasing sushi in the cozy space that seats just six diners at a time.
If you're looking for more delicious tasting menus around town, Jeong will open your eyes to Korean cuisine. Schwa's easy-to-miss exterior and irreverent selctions of hip hop or heavy metal music in the dining room make this one of the hippest dining experiences you can have in town. Oriole, Smyth and Next all have Michelin stars to complement their ever-evolving menus, too.
Photo via Facebook/Lagunitas Chicago TapRoom
For those with exquisite taste buds, why not plan out your own brewery or distillery tour? There’s no shortage of them in Chicago. Not only will you be creating a unique experience for you and your date, but you’ll also support local Chicago businesses in the process! Sounds like a win for everyone.
Photo via Facebook/Field Museum
From art to zoology to natural history to science to local history, Chicago is home to dozens of world-class museums. Add some cultural conversation to your next date night by visiting one of them.
Photo via Facebook/360 Chicago
The best views of Chicago are from up top. Take your date for dinner or drinks at The Signature Room on the 95th floor of 875 N. Michigan (formerly the Hancock Center). Across town, the Willis Tower’s Skydeck also provides thrills and cute photos opps.
Take a morning stroll on the lakefront on one of Chicago's best beaches and welcome the early rays with the sunshine of your life. Not only will your date be impressed by the views, but they’ll be blown away by the fact that you got out of bed before 6 a.m. just for them. That’s real love.
(Promontory Point also offers one of our favorite views of the city for our South Side lakefront lovers.)
Photo via Facebook/The Pleasure Chest
If you’re looking to spice things up with your boo, then Pleasure Chest is your go-to spot. Not only do they have a wide selection of goodies that are sure to spark some flames, but they also hold many workshops for those looking to learn a new trick or two. Not near by Pleasure Chest? Check out Chicago's other Independent Sex Shops.
Photo via Facebook/iO Chicago
Laughter is the world’s best ice breaker and Chicago’s legendary comedy scene is the cause for much of it over the years. See local and out-of-town comedians at Chicago’s best comedy clubs like Laugh Factory and Zanies. If you think the mood calls for improv instead, Second City is our go-to.
Chicago's River Walk in a hidden gem in plain view. The warm months coax dozens of riverside bars, restaurants and events out of winter hibernation. Start at one end and walk through the heart of the Loop until you come across food, drinks or activities that spark your interest. It's a Chicago-style choose-your-own-adventure date!
photo via facebook.com/foxinaboxchicago
A couple that typically works together, stays together. This is the perfect opportunity to actually test that theory. Fox In a Box, The Paniq Room, and The Quandary are some of Chicago's best escape rooms. Be stuck in a prison room, a lab room, a haunted room etc. for an hour, only given puzzles and riddles to solve. You and your special person will have to work together to escape before the time runs out! Fun and accelerating, if you ask us.
Photo via Facebook/United Center
If you're into sports, professional games are always fun to attend. Whether it's Chicago Bulls, Chicago Sky, The Cubs, The White Sox, The Blackhawks or the Bears, there are always games to watch. Sip on a soda, eat some popcorn and root on the team you both love best.
Whatever you decide on, we're confident you'll knock this date out of the park. You've already got the best wingman in the world on your side: the city of Chicago. Good luck, lovebirds! Did we miss your favorite date night idea?? Let us know at [email protected]
