20 Best Chicago Date Ideas for an Unbelievably Fun Date


8 min read
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View of the Chicago skyline with water, skyscrapers, and blue sky
Chicago offers many things for couples to do, whether you live there or are visiting

Chicago, in Illinois, United States, is a vibrant urban city filled with unique attractions. From high-end restaurants and eclectic bars to famous landmarks and outdoor activities, there's so much to do in this popular city.

You’ll also discover an incredible range of romantic things to do in Chicago, IL. Whether you live in the Windy City or are visiting with your partner, these 20 best Chicago date ideas are sure to please everyone!

  • 20 date ideas

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Chicago Date Ideas Map

Using the map of Chicago, you can explore all the date ideas.

Explore the Chicago History Museum

If you and your date want to learn more about Chicago, then a trip to the Chicago History Museum is a must. There will definitely be a lot to discuss with your date as you discover various exhibits covering Chicago history.

Chicago History Museum additionally hosts events such as walking tours. They occasionally have happy hour socials, too; you can grab a drink and explore the museum at this adult-only event.

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The inside of a botanical conservatory with glass ceiling and green and purple plants
Visiting Garfield Park Conservatory is one of the best Chicago date ideas

Visit Garfield Park Conservatory

A visit to Garfield Park Conservatory is an awesome free date idea in Chicago. This stunning indoor botanical garden features an array of stunning plant species, from palms and cacti to ferns and lily pads.

Once you’ve explored the indoor gardens, head outside to wander around the beautiful outdoor gardens.

Not only is this date free, but walking around the gardens together is a great shared experience. You can also take lots of cute photos with stunning tropical plant backdrops!

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Be amazed at the Chicago Magic Lounge

If looking for unique date ideas in Chicago, then a trip to the Chicago Magic Lounge is a must! The bar has three rooms to check out with a range of magic shows in each.

The magic bar shows performances in a close-up setting and allows you to interact with the magician. Alternatively, you can watch a more relaxed show in the music and magic bar.

Of course, tasty food and drinks are on offer to enjoy as you watch the spectacle.

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Relax at AIRE Ancient Baths

What better date idea than relaxing with your partner in an urban spa, like AIRE? Found on River West, this Chicago location is just one of six AIRE spas worldwide.

You can simply pay admission to enjoy the baths or choose from a range of experiences. These include massages and salt rubs. They even have experiences for two - an incredible way to spoil and connect with your date.

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Watching the fireworks at the Navy Pier is one of the best Chicago date ideas to do
Watching the Navy Pier fireworks is a fun thing for couples to do in Chicago

Watch the fireworks at Navy Pier

You'll discover many things to do at Navy Pier, from checking out the restaurants to riding the centennial wheel. One of the best Chicago date ideas is to watch the fireworks at Navy Pier.

The fireworks show happens twice weekly on Wednesdays and Saturdays. The show lasts 10 minutes, during which time you and your date can enjoy the colorful illuminated display. Checking out the Navy Pier fireworks will surely make your date pop!

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Spend the day at the Lincoln Park Zoo

Having a day date with your partner and some cute animals is always a good idea! A trip to the Lincoln Park Zoo will allow you to get up close with a range of creatures. From camels and zebras to snow leopards and even polar bears, you won’t get bored as you move between enclosures.

The zoo also hosts some fun events, including a cocktail mixing class and an adults-only night. Check the calendar to see what’s on when you and your date visit.

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Bond over a cooking class

Going on a dinner date is a failsafe idea, but learning to cook incredible dishes together is much more fun! There are many cooking classes in Chicago, most of which are also BYOB.

Cook au Vin is a classy choice for a date. You’ll learn how to cook French classics such as Tarte Tatin, souffle, and Coq au Vin. They also have pastry and bread-making classes. If your date loves desserts, also check out Give Me Some Sugar’s classes.

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An aerial view of Chicago with water, sand, a park, and skyscrapers
To wow your date, take them on a helicopter tour to see Chicago from above

See Chicago from above on a helicopter tour

Why stay on the ground for your Chicago date?! Taking a helicopter tour over the city is a fun, unique, and memorable idea sure to wow your partner!

Chicago Skyline Helicopter Tour offers private helicopter tours of the city that provide incredible bird's-eye views. The 45-minute tour takes you over a range of well-known spots, including Navy Pier and Millennium Park.

This highly exciting date idea is sure to create long-lasting memories for you and your partner!

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Check out the best happy hours in the city

Instead of settling on one bar, try a happy hour bar crawl. This fun idea for date night in Chicago allows you to visit multiple spots without breaking the bank.

Virtue is a cool bar to check out first. They have happy hour deals on mixed drinks, wine, beer, and snacks. Next, head to Stella Barra with discounted pizzas, meatballs, and beverages.

Other places with great happy hours include Chef’s Special Bar, Bernie’s, and Nico Osteria.

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Meet furry friends at a cat cafe

Is your date an animal lover? Then visiting one of Chicago’s cat cafes is a must. Windy Kitty is a downtown Chicago cat cafe that allows you to enjoy a snack and drink while playing with cute kitties.

If you haven’t got your fill of furry friends, head to Catcade, another central cat cafe. Tree House Humane Society Cat Cafe, just outside of downtown, is also an excellent spot.

Cats at all locations are adoptable, too, so you may end up going home with an additional friend!

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A planetarium with a dome roof next to a glass building with a sculpture in front
Chicago's Alder Planetarium is a fun date spot with adult-only evenings

Enjoy drinks at Adler Planetarium After Dark

A trip to the Planetarium isn’t just for kids! Visiting this astronomical location is a fun date idea any time of the week. However, taking your date to Adler Planetarium during their After Darks event is a great way to keep the date sophisticated.

The event is held on the third Thursday of most months (subject to change) and allows adults-only to explore the Planetarium between 6.30 pm and 10 pm.

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Tackle a rock climb

If looking for fun date ideas in Chicago and you enjoy adventure activities, then be sure to go to Brooklyn Boulders. This indoor rock climbing venue has two Chicago locations, one near Lincoln Park and one in the West Loop.

Brooklyn Boulders offers a range of walls to climb for all levels, and you have the option to climb with or without a harness. You and your date can also take a class or have a private climbing lesson.

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Challenge your date to a bowling game

Get competitive by challenging your date to a bowling game. Chicago has a range of fun bowling lanes that also offer food and alcoholic drinks.

10pin, for example, offers nightclub-style music and lighting along with a drink menu, martini list, and small plates. Other cool bowling spots to check out include Pinstripes and Waveland Bowl. Many of the lanes have billiards, air hockey, and the like too.

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A building with a glass roof with grass, trees and plants, and a lamp in front
The Lincoln Park Conservatory features beautiful flora and even dinosaurs!

Explore the Lincoln Park Conservatory

The Lincoln Park Conservatory is another beautiful indoor botanical garden in Chicago. You’ll discover a range of tropical plants such as palm trees and orchids.

There’s also a Show Room that hosts an annual flower show and houses beautiful vibrant flowers the rest of the year.

A unique feature here is that you may see a dinosaur! There are dinosaurs hidden all around the conservatory, and you and your date can compete to find the most.

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Go on a brewery tour

Going on a brewery tour is one of many super fun things for couples to do in Chicago. You and your date can plan a tour yourselves, hitting all your favorite spots or places you want to try.

Alternatively, you can go on an organized brewery tour. Chicago Beer Experience is a great choice that offers a selection of different brewery tours.

Options to choose from include a Bacon and Brews tour and a Sins and Suds tour that looks at “beer's influence on Chicago’s criminal past.”

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Go Kayaking on the Chicago River

If you and your date love outdoor activities, then kayaking on the Chicago River is the perfect date idea. The Chicago River Kayak Tour offers kayaking tours that will take you past some of Chicago's main attractions.

Things to see include Wrigley Field, the Lyric Opera building, and many more. While on this two-and-a-half-hour tour, you'll also learn more about Chicago's history, culture, and architecture.

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Fans watching a baseball game at a baseball field with a city skyline in the back
If your date is a sports-lover, take them to watch one of Chicago's sports teams

Watch Chicago’s sports teams in action

Chicago is one of the few cities to have a team in all four major US sports leagues: the Bears in the NFL, Blackhawks in the NHL, Bulls in the NBA, and Cubs in MLB.

Heading to one of these teams’ games is a super fun date idea. Even if your partner isn’t a major sports fan, grabbing some drinks and cheering for the home team never disappoints.

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Play arcade games at Headquarters Beercade

Located in Chicago’s River North neighborhood, HQ Beercade is a super cool date spot. The bar has a fun selection of over 50 arcade games, including Pac-Man and Asteroids. You can also play pinball or challenge yourself and your date to winning their trivia night.

While you explore the arcade, you can enjoy snacks, craft beers, and specialty cocktails. Beercade also has sharing cocktails, perfect for enjoying with your date.

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Dare to go on the Gangsters and Ghosts tour

Chicago has a rich but criminal history. Due to this, historical and ghost tours are popular in the city. If you’re after some fun couple activities in Chicago, then going on the Gangsters and Ghosts walking tour is a must.

You’ll visit a range of haunted buildings and gangster hangouts. Tales involve the city’s notorious gangsters, like Al Capone, and the culture of speakeasies during prohibition.

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A building with glass windows by the water with a city skyline in the background
You can check out amazing marine creatures with your date at Shedd Aquarium

Discover marine life at Shedd Aquarium

Taking your date to Shedd Aquarium is a fun and laid-back idea. Exciting creatures to see include giant octopi, beluga whales, and sharks. You’ll also spot otters, penguins, and a colorful array of fish and corals, among many other marine animals.

Once you’ve seen all the exhibits, check out the pretty gardens or head to the terrace for drinks and views of the pier.

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In Conclusion

Chicago is a fantastic city, featuring a range of incredible date spots. No matter what you and your partner enjoy doing, you're sure to have a blast when trying any of these best Chicago date ideas!

This article was edited by Loredana Elena.

For some great articles about date ideas, check out:


Written by Alli Sewell

allisewell WRITER Currently based in Canada, I've also lived and worked in the UK and Brazil and travelled in North and South America, Europe, Australia, and Asia. I love finding the best photo-ops and food and drink locations wherever I go!


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