35 Best Chicago Date Ideas for an Unbelievably Fun Date


16 min read
Aerial of the Chicago skyline with water, skyscrapers, and a sunset 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 35 best Chicago date ideas are sure to please everyone!

  • 35 Chicago date ideas

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35 Best Date Ideas in Chicago

Chicago Date Ideas Map

A map of Chicago. Use the map to 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 and Illinois 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 at this famous Chicago landmark, 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 night 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 date night in Chicago idea allows you to visit multiple spots without breaking the bank.

Stella Barrais a cool bar and restaurant to check out first. They have happy hour deals on pizzas, meatballs, and beverages. Other places with great happy hours include The Press Room, Bernie’s, and the The Franklin Room, which has a daily whiskey happy hour.

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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. Catcade is a downtown Chicago cat cafe that allows you to hang out and play with cute kitties. The cafe also has retro arcade games that you can play and there's free wifi if you and your date want to get some work or studying done together.

The cats that live at Catcade 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. As you kayak down the river, you'll pass some of Chicago's main attractions.

Places to see include Wrigley Field and the Lyric Opera building. If you're looking for a date night idea, consider kayaking on the river during the Navy Pier fireworks.

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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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Work together to tackle an escape game

A great way to bond is by working together to solve an escape game. The Escape Game Chicago has a selection of themed escape rooms to choose from.

Themes include “Special Ops,” “Prison Break,” and “The Heist.” You and your date will have an hour to solve puzzles in order to break free from the escape room. Even if you don’t manage to solve the puzzles in time, you’re sure to have fun trying!

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A skyline with water in front of it at sunset
Watch the sunset over Chicago on a Lake Michigan dinner cruise

Luxuriate on a Lake Michigan dinner cruise

If you and your partner want to treat yourselves, going on a luxury dinner cruise on Lake Michigan is a must. You’ll get to enjoy a three-course meal and drinks, including beer, wine, and cocktails. As you wine and dine, you can admire the views of Lake Michigan and the Chicago skyline.

There’s also a DJ aboard so that you can dance to live music, and there’s a rooftop deck to hang out on. A Lake Michigan dinner cruise has to be on your Chicago itinerary when visiting with your loved one.

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Taste the best dishes in Chicago on a food tour

One of the fun things to do in Chicago for couples that like trying new dishes is going on a food tour. Your guide will take you to a selection of the best eateries in the Windy City. Snacks to try include brownies, hot dogs, deep-dish pizza, and much more. You’ll also get to try some local craft beer.

Along the route, you also get to pass a few of the famous landmarks in Illinois. Places to see include Millennium Park and Cloud Gate, the Wrigley Building, and the Magnificent Mile.

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A lion statue outside of a stone museum building
You can see works by famous artists at the Art Institute of Chicago

See artworks at the Art Institute of Chicago

One of Chicago’s best cultural attractions is the Art Institute of Chicago. The museum is one of the oldest and largest art galleries in the world and houses some famous artworks.

Exhibitions at the gallery cover a range of art mediums and feature art from Europe, Asia, the Americas, and more. Some of the renowned artists with pieces on display include Georges Seurat, Claude Monet, and Henri Matisse.

To make admission and exploring the museum a breeze, purchase Art Institute of Chicago skip-the-line and guided tour tickets in advance.

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Listen to classical music at the Chicago Symphony Orchestra

Another of the great cultural activities to enjoy with your date is going to see the Chicago Symphony Orchestra. The orchestra was founded in 1891 and generally plays in Orchestra Hall.

You can see a range of classical concerts at the venue and may occasionally be able to see other genres of music. The Chicago Symphony Orchestra is the main act to see here, although other artists and groups do perform too.

Spending an evening at the Chicago Symphony Orchestra is definitely one of the best things to do at night in Chicago.

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Get crafty at a graffiti art workshop

One of the most fun Chicago date ideas is going to a graffiti art workshop. During the art class, you’ll learn how to create street art murals. Your instructor will teach you different styles and techniques so that you can create your own urban art masterpiece.

This workshop is also BYOB, so you can sip on some drinks while you get creative. The classes are for artists of all abilities, so they're perfect for anyone that enjoys artistic activities. Best of all, you and your date will have a one-of-a-kind art piece to take home.

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A park with grass that has a metal structure above it and a skyline in the background
Millennium Park hosts outdoor movies in the summer months

Hang out and watch a movie at Millennium Park

Millennium Park is an ideal place to hang out with your date and take a romantic walk. In the summer, you can also head to the park to watch an outdoor movie. The movies generally run from July through August.

You can see a different fan-favorite movie at each showing and enjoy the film in the fresh air. Be sure to take a comfy blanket, snacks, and drinks as well so you can relax in style in front of the big screen.

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Try delicious sweet treats on a donut tour

For couples who love desserts, a Chicago donut tour can’t be missed! This tasty tour will take you and your other half to four of the city’s best donut shops, all of which are located around The Loop. Bakeries to stop by are Doughnut Vault, Firecakes Donuts, Stan’s Donuts & Coffee, Do-Rite Donuts & Chicken.

At each stop, you’ll get to taste some signature donuts. As you walk to each shop, you’ll get to see some landmarks and learn some Chicago history and fun facts from your guide. The stores often also have vegan, gluten-free, and nut-free options.

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High rise buildings illuminated at night
Enjoy views of Chicago while at a rooftop bar with your date

Sip drinks and enjoy the views at a rooftop bar

One of the most fun ways for you and your date to take in the views of Chicago is from a rooftop bar. A popular rooftop bar in the city is found at The Robey Hotel. This stylish drinking spot has both an indoor “rooftop” lounge with views across the city and an outdoor poolside bar.

Drinks on offer include unique cocktails, champagne and sparkling wine, and beer. You can also enjoy bar snacks, like jalapeno wontons or Nashville fried chicken sandwiches.

Raised Bar Chicago is another spot to check out that offers food and delicious drinks.

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Share a romantic dinner at Alinea

If you and your partner are looking to splurge on a night out, dining at Alinea is highly recommended. The food at Alinea is so renowned, that the restaurant is often named one of, if not the, best restaurants in North America.

When dining at this three Michelin star restaurant, you can enjoy a multi-course tasting menu complete with novel and decadent dishes. The exact dishes you’ll be served vary, with seasonal produce often being used.

Along with tasting incredible, each plate looks stunning! No matter what is on the menu when you visit, you’re guaranteed to try combinations you’ve never had before.

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Find some unique pieces at Chicago’s thrift shops

A great daytime date idea is going thrift shopping. Chicago has a host of thrift stores to choose from in and around downtown. Crossroads Trading is a local favorite. This store has lightly worn name-brand clothes at affordable prices.

Another spot to check out is Green Element Resale. While exploring this thrift shop, you’ll discover a host of items, from housewares and books to clothing and accessories. There’s also a large Buffalo Exchange close to downtown Chicago, which sells an array of second-hand clothing, including chain store brands and designer and vintage pieces.

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A Greek-style museum building with a banner with a dinosaur skeleton on it
There are many exhibits to see at the Field Museum of Natural History

Learn something new at the Field Museum of Natural History

Chicago’s Field Museum of Natural History is one of the largest natural history museums in the world. The museum was established in 1894 and is one of the most renowned cultural attractions in the city.

During a visit, you and your date can learn about a range of fascinating topics. Exhibitions to see include those on dinosaurs and fossils, cultures of the world, and wildlife and conservation.

You’ll also be able to see Sue, the museum’s dinosaur skeleton! This skeleton is the biggest and most complete Tyrannosaurus Rex skeleton in the world.

The Field Museum of Natural History is generally open from 9 AM to 5 PM, making it another great spot for a daytime date.

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Have brunch together

Another of the most romantic things to do in Chicago for couples is going to brunch together. Chicago residents love going to weekend brunch, so you can find many options across the city.

If you can't decide where to go, consider visiting Another Bite. They serve a great selection of pancakes, waffles, and French toast. Unique dishes include Fruity Pebble French toast and Oreo pancakes.

Alternatively, a great plant-based choice for brunch is Bloom Plant Based Kitchen. You can order brunch on Sundays from 11 AM to 3 PM. Delicious dishes include churro waffles, chickpea frittata, and pancakes with maple syrup and vegan whipped cream.

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Try the best deep dish pizza in the city

The Windy City is known for its deep-dish pizza. If you’re looking for the best pizzerias in the city to try this local treat, one of the cute date ideas in Chicago to try is going on a pizza tour!

This experience allows you and your date to visit six top deep-dish pizza restaurants. At each stop, you can sample the freshly made pies and may even find a new favorite pizza date spot. The route also takes you past some famous attractions, including Grant Park, Lincoln Park, and the United Center.

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A museum building with steps leading up to it and yellow "MCA" signs on it
The Museum of Contemporary Art is a fun date spot for art lovers

Visit the Chicago Museum of Contemporary Art

Another of the best date spots in Chicago for art lovers is the Chicago Museum of Contemporary Art. Located downtown, the museum was opened in 1967. It’s one of the largest contemporary art galleries in the world and features works by many famous artists.

Renowned artists with pieces on display include Andy Warhol and Edward Krasinski. You can also see a range of mediums at the gallery, including paintings, drawings, and photographs.

Along with the permanent collection, the Chicago Museum of Contemporary Art has temporary exhibits and hosts voracious events.

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In Summary

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 Chicago date activities!

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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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