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!
Photo via Facebook/Steppenwolf Theatre Company
Chicago is home to amazing independent theaters and productions 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. The Annoyance Theatre skirts the line between scripted and improvised plays. 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 via Facebook/Chicago Magic Lounge
Magic? Yes, it really can be romantic. Andersonville’s Chicago Magic Lounge does everything right to make itself an out-of-the-box date destination. A classy cocktail lounge with parlor and card trick performances nightly marks the start of your evening. If you decide you want to commit further, get tickets to a show on the theater’s beautiful mainstage.
Photo via WheelFunRentals.com
This one’s a timeless classic. You, a smoking hot date, a boat, various sea creatures singing “Kiss The Girl”...wait, we’re thinking of The Little Mermaid. Anyway, you can’t go wrong with a swan boat cruise on the pond in Humboldt Park. Kissing optional but recommended.
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, visit a museum dedicated to pizza, stroll through Chicago’s largest collection of leatherwear, watch pimps do improv 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. 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
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/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?
Photo via Facebook/The Aviary
Splurging at one of Chicago’s hottest cocktail bars is never a bad thing. Learn the true meaning of “mixology” at The Aviary. Watch live music and get cozy in a booth with a couple of classic cocktails at California Clipper. Pretend you're living your best beach life with Lost Lake’s tiki menu and massive rum selection. If you both just want some new booze in your life, try one of the best new bars in Chicago.
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 coolest new places to dine around town. Check out our guide of the best new restaurants in Chicago. Make sure you have plenty of conversation topics lined up though because the wait times for a table at these cool new spots can sometimes be lengthy.
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. If you and your S/O are feeling frugal, most museums offer free admission days throughout the year. Check out which museums stay open later if you need to plan around your day jobs.
Photo via Facebook/Spirit Of Chicago
It’s undeniable that Chicago's skyline is romantic, especially at night, so what better way to see it than while enjoying a nice dinner cruise? It’ll also give you a chance to dress up and really impress your date. Most dinner cruises depart from Navy Pier, so start there on your quest to find the right one for you and your first mate.
Photo via Facebook/Chicago Helicopter Experience
Yes, Chicago’s skyline is beautiful and romantic, but have you ever seen it from above? Chicago Helicopter Experience offers day and night tours of the downtown area. Soar high above the tallest skyscrapers with your sweetheart!
Photo via Facebook/Navy Pier
Find romance 200 feet above Navy Pier courtesy of the Cenntenial Wheel. The view is beautiful, and we’re sure you’ll find some way to pass the time on the way up (and down). It’s also open all year round!
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). 360 Chicago one floor down also provides beautiful panoramic views, its own bar and the chance to test your crush’s tolerance for thrills on Tilt! Across town, the Willis Tower’s Skydeck also provides thrills and cute photos opps.
Take a morning stroll on the lakefront 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.
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, iO Theater and Second City are our go-to's.
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!
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!