Fun Date Night Ideas in Chicago

Happy hour or dinner and a movie – date night classics. You can’t go wrong with these activities, but after a while, they start to get stale. 

Whether you’re going on a first date or a fiftieth date, there are plenty of ways you can spice things up. But in an incredible city like Chicago, there’s almost too much fun stuff to do. Where do you even start?

Don’t worry; we’ve got you covered. Keep reading to discover some of the best fun date night ideas in Chicago.

Relax at the AIRE Ancient Baths

Treat your date to a luxurious experience at the AIRE Ancient Baths. Let your stress melt away in traditional Roman, Greek, and Ottoman baths. AIRE offers several experiences for couples, including full-body massages and wine tastings.

Go for a Swan Boat Ride in Humboldt Park

Head over to Humboldt Park and take your date for a romantic cruise in a  swan paddle boat on the park’s lagoon. Get cozy in these intimate boats and take in all the beautiful scenery. If you’re not a fan of water, rent bikes instead and go for a ride around the park. 

Laugh It Up at a Comedy Show

Chicago’s comedy scene is legendary, with many of today’s top comedians getting their start here. If you love a good laugh, take your date to one of Chicago’s best comedy clubs, Laugh Factory or Zanies. If improv is your thing, head over to Second City or iO Chicago.

Go on a Brewery Crawl

There’s no shortage of breweries in Chicago, so why not spend an afternoon sampling some delicious craft beers? Head over to Malt Row in Ravenswood, where you’ll find several of Chicago’s best breweries offering several different kinds of beer. 

Have a Picnic in the Park

No matter what part of the city you’re in, there’s sure to be a park nearby. Pack lunch and a cozy blanket, and head over to your neighborhood park for the perfect picnic with your date.

Go to a Museum

Chicago has several excellent museums, covering everything from art to natural history to science. Start your day in the Loop at the world-famous Art Institute of Chicago. From there, head down to the Museum Campus and take in the Field Museum, the Adler Planetarium, and the Shedd Aquarium.

Take a Walk Along the 16th Street Mural Wall

Chicago is a city of neighborhoods, and there’s plenty to explore off the beaten path. Head over to Pilsen and take a walk along the 16th street mural wall, stretching from Halsted Street to Western Avenue. Snap some pictures along the way and discuss your favorite murals over a drink in one of Pilsen’s many neighborhood bars.

Go to a Movie at the Drive-In

Take your typical movie date night to the next level and head over to ChiTown Movies. This drive-in theater, located in Pilsen, features a rotating lineup of new and classic movies. If you have a soft spot for nostalgia, this is the date spot for you.

Immerse Yourself in Nature

Chicago is an urban jungle, but there are still plenty of opportunities to connect with nature. Head over to Garfield Park Conservatory or the Chicago Botanic Garden and take in all the beautiful flowers and greenery. Or take a hike through one of the many forest preserves located throughout the metropolitan area.

Go to a Show at the Theater

If you’re sick of movies, take in a live show at one of Chicago’s many local theaters. The Steppenwolf Theather in Lincoln Park and the Goodman Theater in the Loop always put on incredible productions. If musicals are your thing, head to the Cadillac Palace Theater or the CIBC Theater to catch a Broadway show.

Take a Class Together

Learning a new skill together makes for a great date night. Head over to the Chopping Block for a cooking class. Or get creative at a sip-and-paint class at Bottle & Bottega.

Go to Lincoln Park Zoo

Lincoln Park Zoo is one of Chicago’s top attractions and is a great place to bring your date. Who doesn’t love watching monkeys swing through the trees or seals frolicking through the water? If you want to avoid herds of small children, check out one of their adult-only events.

Take in the Views From Above the City

Get your heart racing while taking in some gorgeous views of the city. Take your date for drinks at the Signature Room on the 95th floor of the former John Hancock Center. Or take in the views at the Skydeck at the Willis Tower.

Go on a Scavenger Hunt

Take sightseeing to the next level and go on a scavenger hunt. Solve puzzles with your date and learn about what makes Chicago so special. If local history is your thing, then this will be right up your alley.

Conquer an Escape Room

An escape room isn’t the most romantic date night in Chicago, but it’s a great way to get to know your special someone. If you can escape a prison or a haunted house together, then you can tackle any challenges together. The Escape Game, Fox in a Box, and PanIQ are some of the best escape rooms in Chicago.

Go to an Arcade Bar

Chicago arcade bars, like Emporium, make for a fun and unique date. These bars have all kinds of classic games, from Super Mario Bros to Mortal Kombat. If arcade games aren’t your thing, try pinball or air hockey instead.

More Fun Date Night Ideas

Chicago is an amazing city with no shortage of fun things to do. Whether you’re looking for romance or adventure, or something in between, you’re sure to find the perfect activity for your date night.

Looking for more fun date night ideas? Check out our upcoming events at all three of our Chicago locations!

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