12 Creative Date Night Ideas In Chicago (2024)

Looking for unique date night ideas in Chicago? Then we have some good news for you! “The Windy City” has so much to offer people looking to break the mold from the usual bar or coffee date.

As the largest online marketplace for hourly venue rentals, Peerspace makes it easy to book unique spaces in Chicago and beyond that provide you and your date with new, fun experiences. There’s something for every kind of budget or occasion if you know where to look, so check out our Peerspace venue suggestions along with this list of 12 of the best date ideas Chicago has to offer!

1. Go on a classic drive-in movie date

In most parts of the country, a drive-in movie date is something that you’re only going to see on a movie or television show. Daters in Chicago are lucky enough to have the option to see a movie from their car at ChiTown movies! Showings include both classics and new releases, along with themed showings for different holidays.

Looking for a little more privacy? Then you need to check out Peerspace, where you can rent private movie theater rentals just about anywhere. For example, check out the home theater at this local gray stone home in South Shore. Along with the amazing screening room, you and your date also have access to the home’s jacuzzi, game room, and private backyard! It will be like a mini vacay without leaving Chi town.

2. Skip the screen and explore Chicago’s theater scene

If the whole reason you’re going on a date is to get away from the screens, Chicago has a thriving local theater scene for you to explore. The Steppenwolf has been a fixture in the scene for over 40 years and shows up to 16 different plays a year. Take a date and see why they hold such high regard in the theater scene!

3. Relive history at a speakeasy bar

For better or for worse, Chicago has a reputation in history for being home to some of the most infamous prohibition-era gangsters. Take a trip back to the past with your date at your own private speakeasy! For some extra fun, immerse yourself in the experience by putting on period-appropriate outfits or costumes.

As you can see, Peerspace has access to some of the best private party spaces, including truly amazing locations around the city like this. The platform opens up a whole new world of options for daters looking to enjoy a private, intimate experience.

Check out some of our favorite Chicago photoshoot rooms to uplevel your content!

4. See the animals at the Lincoln Park Zoo

It’s always a safe bet to have a first date somewhere that generates easy conversation. Looking at the wide variety of wildlife at the Lincoln Park Zoo is an easy way to break the ice in a safe, public environment. They are always hosting events, so check out one of the adults-only nights for one of the most reliable date ideas in Chicago!

5. Paddle a swan boat at Humboldt Park

The swan paddle boat ride is an iconic image of romance that has been enjoyed by couples for decades in Humboldt Park. Get to know your date as you take in the sights with Wheel Fun Rentals, the only place in the park to get your hands on one of their swan boats. If dry land is more your thing, they also offer four-wheel bikes that you can explore the park on.

6. Snap some pics in a curated creative space

If you know where to look, there are dozens of spaces curated for the perfect couples’ photoshoot. Peerspace is the best place to find hidden gems, like this amazing video and photo studio in Garfield Park!

They have brightly lit neon walls and 10 distinct that will give you plenty of opportunities for ‘grammable pics. We love the grass wall set with a lit-up LOVE sign. Perfect for date night, especially if you two are an established couple! Through Peerspace you can find some truly great spaces all around the city that are available to rent by the hour, so you don’t have to worry about booking something for the entire night.

“A very cool place,” shares a Peerspace reviewer who took snaps here. “Larry has a lot of fascinating stuff here and you could use this for many different projects. He was very helpful and he’s a very cool dude!”

7. Escape to a hidden oasis at Garfield Park Conservatory

Some days, living in the city will make you ache to see some greenery. Chicagoans are lucky to have Garfield Park Conservatory as a date option to get all the plant life you need. One of the largest in the country, this is one of the most spectacular date ideas in Chicago that will impress your date without costing an arm and a leg.

8. Get your blood pumping with an exercise date on the North Shore Channel Trail

Stretch your legs by taking your date on a stroll along the Chicago River at the North Shore Channel Trail. Or, if you’d like to see more, take your bikes down the long and scenic bike path. The trail extends for only about seven miles, so it wouldn’t be too hard to see the whole thing in one day on a bike.

9. Play some Pac-Man alongside a cat at the Catcade

By now, you’ve probably heard of the concept or been to a cat cafe. In a unique twist, the geekier daters and cat lovers can play some arcade classics at the Catcade on Belmont Avenue. Be careful, you might just end up falling in love with one of the furry residents and want to take them home. Reservations are required, so be sure to plan this one in advance.

Our great places to find photoshoot inspiration in Chicago may also provide some date spot inspo. Check them out!

10. Soak in the Chicago skyline with a drink in hand

Chicago’s city skyline is a sight to behold but can feel inaccessible at times. That’s where Peerspace comes in handy. You can use them to get a backstage pass to one of the best skyline views in the city! This contemporary two-story penthouse in Lake View is a classy location to get an intimate and private view of the city on its spacious roof deck that will be all yours for as long as you book it.

The fact that there’s a chef’s kitchen and sound system means you can also cook dinner together and share a romantic dance after. Just another example of the unique date ideas in Chicago that Peerspace can serve up.

11. Spend the day at one The Plant

For an all-encompassing date, take a few hours to see everything that The Plant has to offer. A Chicago institution based all around sustainability, they are the home to local farmer’s markets and businesses. They also have plenty of classes or events that they put on for the community, so take on with your date, and learn something new about keeping the city clean and sustainable.

12. Have dinner aboard a boat on Lake Michigan

Dinner cruises are a tried and true romantic date. In Chicago, you can enjoy a world-class meal while you tour around Lake Michigan. Check out Navy Pier and see what kind of delicious seasonal plates they’re serving up for their guests! When you’re back on dry land you can enjoy a view of the lake from their classic ferris wheel.

Date night ideas in Chicago: conclusion

As you can see, Chicago is a city filled with fun things for couples to enjoy. But when you prefer a private, bespoke experience, rely on Peerspace to connect you to stylish, well-equipped event venues in Chicago that turn your typical date night into something special.

Find unique date night venues in Chicago on Peerspace