21 Incredible Date Ideas in Chicago

Last Updated on August 26, 2022 | 0 Comments
fun date ideas in chicago
Last Updated on August 26, 2022 | 0 Comments

Looking for incredible date ideas in Chicago? Whether you're about to embark on a first date with someone special or are planning something fun for your 10th anniversary, date ideas in Chicago abound!

Between the dramatic skyline, the sweeping views of the lake, the world-class restaurants and the glistening lights, the Windy City is an excellent backdrop for an incredible date night. Whether you’re looking for something relaxing and romantic or outdoorsy and adventurous, you can’t go wrong with any of these 21 date ideas in Chicago.


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Foodie Date Ideas in Chicago 

1. Cooking Classes

Cooking classes in Chicago are some of the best date experiences in all of the Windy City. Led by the city’s best chefs, classes not only help boost your confidence in the kitchen, but give you and your date an opportunity to explore new ingredients, techniques and types of cuisine. You can even choose from a wide variety of online cooking classes for an intimate date night in!

cooking classes are a fun date idea in chicago
via Cozymeal

2. Food Tours

Treat your date to a culinary and cultural stroll around vibrant and tasty neighborhoods with guided food tours in Chicago. By combining iconic Chicago food tastings with fascinating stories, local culture, history and architecture, you’ll have the perfect recipe for one of the best date ideas in Chicago.

woman holding a chicago style hot dog on a food tour
via Cozymeal

3. Private Chef Experiences

Why not hire a private chef for a romantic date night in Chicago? Private chef experiences feature multi-course menus prepared by local world-class chefs. You and your date can choose the cuisine, date and time, and a private chef in Chicago will source the finest ingredients and bring the necessary equipment to your place to prepare an incredible meal with cleanup provided at the end.

private chef experiences are a fun date idea in chicago
via Cozymeal

4. Winery Tours and Tastings

Embark on a winery tour or wine tasting in Chicago for a classic date night activity! There are many opportunities to taste a selection of amazing wines made locally as well as varieties hailing from the world’s top wine regions. Enjoy a wine flight together and be sure to take a bottle or two home to save for a later date!

couple toasting wine glasses at a vineyard
via Canva

5. Brewery Tours and Tastings

With so many amazing breweries situated throughout the city, brewery tours and tastings offer up everything from extra-hoppy IPAs to dark, decadent stouts. Walk among the fermentation tanks and learn more about the beer-making process on a Chicago brewery tour, where experts will explain how your favorite beverages are crafted. 

brewmaster pouring a pint of beer at a brewery
via Canva

6. Share a Meal at Sun Wah BBQ

Sun Wah BBQ is one of the best restaurants in Chicago and serves one of the most iconic Chicago foods: the off-menu Beijing duck dinner. Sharing this not-so-secret signature dish with your special someone is one of the best date ideas in Chicago. 

This multi-course feast starts with an entire duck, freshly roasted and carved tableside. You’ll also enjoy steamed bao with garnishes and house-blended hoisin sauce. Then, what remains of the duck is returned to the kitchen where lingering morsels are made into the second course: duck fried rice. Finally, the duck bones are simmered into a duck broth soup as the finishing course.

share a meal at sun wah bbq for a fun date idea in chicago
via Sun Wah BBQ

7. Wine and Dine at Geja's Café

Billed as one of the most romantic places in Chicago and one of the 50 best warm and cozy restaurants in the U.S., this charming nook has a long history of providing amorous moments for Chicagoans and visitors alike. You’ll swoon for the Flamenco music and candlelit tables as you enjoy a multi-course fondue experience that includes a cheese course and a meat course, plus lobster tail and fresh scallops for a truly romantic date idea in Chicago.

couple enjoying dinner at geja's cafe
via Geja's Café

Relaxing Date Ideas in Chicago

8. Sip Back and Relax With Virtual Date Ideas in Chicago

Enjoy a crowd-free night in and the opportunity to master the art of cocktail making from home under the guidance of a master mixologist during online mixology classes. You and your date will learn all about classic and contemporary cocktails while enjoying food pairings and taking your mixology skills to the next level. There are also virtual wine tastings that make excellent stay-at-home date ideas in Chicago.

online mixology classes and other experiences are fun date ideas in chicago
via Canva

9. Relax at AIRE Ancient Baths

AIRE is a luxurious modern bathhouse with only six locations worldwide. Visiting AIRE Ancient Baths is one of the most romantic things to do in Chicago and is one of the best anniversary date ideas. At AIRE Ancient Baths, you’ll get a unique, intimate aquatic experience. You and your date will strip down to your swimsuits and try out the various pools, each with different temperatures and salinities.

aire roman baths
via AIRE

Free Date Ideas in Chicago

10. Explore the Garfield Park Conservatory

Chicago’s Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the nation. It’s also free, open year-round and is an incredible date idea in Chicago. Date-goers can enjoy the lush flora and tropical temperatures indoors as well as more than 10 acres of outdoor gardens. 

visit garfield park conservatory for a fun date idea in chicago
via Garfield Park Conservatory

11. Visit the Lincoln Park Zoo

Chicago’s Lincoln Park Zoo is one of the most popular cultural destinations in Illinois and the only privately managed, free zoo in the country. The zoo is home to nearly 200 unique animal species from around the world while the zoo’s landscape is bursting with the colors, textures and scents of more than 1,200 plant species.

chimp at lincoln park zoon in chicago
via Lincoln Park Zoo

12. Listen to Classical Music at the Grant Park Music Festival

For classical music lovers, the annual Grant Park Music Festival is a summertime favorite and a great date idea in Chicago. These outdoor concerts have a laid-back feel, so you can bounce between conversation, listening to the entertainment and people watching. 

grant park music festival
via Grant Park Music Festival

13. Millennium Park Summer Film Series

Pack your own popcorn, bring a blanket and enjoy a free outdoor movie screening during the Millennium Park Summer Film Series for an incredible date idea in Chicago. The Pavilion features a state-of-the-art sound system and outdoor screen that you can see and hear from the front row to the back of the Great Lawn, so there isn't a bad seat in the park!

the millennium park summer film festival is a fun date idea in chicago
via City of Chicago

Outdoorsy Date Ideas in Chicago

14. Kayak the Chicago River

Kayaking between skyscrapers is one of the best outdoorsy date ideas in Chicago! Rent a kayak and paddle at your own pace through steel and concrete canyons or book a kayak tour. Tour options range from an architectural tour to a sunset and city light night tour to a happy hour tour that ends at a tiki party. No matter what you choose, you’ll have the opportunity to see the city from an entirely new perspective.

young couple kayaking on a date
via Canva

15. Bike Along the Lakefront

Chicago’s scenic Lakefront Trail is an 18-mile path that follows the Lake Michigan shoreline on the city’s eastern edge. Biking along this fully-paved trail can be one of the most fun date ideas in Chicago and the perfect car-free way to check out some of the city's most popular beaches, cultural institutions and more!

biking along the lake is a fun date idea in chicago
via Canva

16. Watch the Fireworks at Navy Pier

Enjoy Chicago’s favorite sky spectacle show from Memorial Day weekend through Labor Day weekend for a romantic date idea in Chicago. Find a spot anywhere on Navy Pier or along the nearby lakefront to take in the dazzling display. Fireworks light up the sky twice a week starting at 9:30 p.m. on Wednesdays and 10:15 p.m. on Saturdays. 

fireworks over navy pier in chicago
via Navy Pier

Adventurous Date Ideas in Chicago

17. Take a Helicopter Tour

If you’re looking to elevate your date to the next level, a helicopter tour is the ultimate date night in Chicago. While daytime helicopter tours over Chicago will give you and your date unforgettable panoramic views of Lake Michigan, Millennium Park, Lincoln Park and Grant Park, nighttime helicopter tours over Chicago give you the opportunity to see the sunset over Lake Michigan and watch as millions of gleaming lights on hundreds of skyscrapers turn on for the night.

a helicopter ride is a fun date idea in chicago
via Canva

18. Enjoy a Salsa Night

Chicago has a vivacious Latin dance scene and many hotels and bars downtown (and in the suburbs) host regular salsa nights, which make for great date ideas in Chicago. Some of the most well-known and popular salsa nights in Chicago are at Dylan’s Tavern and Grill, Nacional 27, Alhambra and Palm Court at the Drake Hotel. Most salsa nights even start off with an introductory lesson.

couple salsa dancing in a ballroom
via Canva

Artistic Date Ideas in Chicago

19. Tour Chicago Avenue’s Best Art Galleries

If you find yourself strolling between Ashland Avenue and Wood Street, you'll find some of Chicago's best art galleries, providing the opportunity for a DIY art crawl. Start your tour at Matthew Rachman Gallery, then head west. You'll come across other local staples like DOCUMENT, Volume, the Rhona Hoffman Gallery and more for an artistic date idea in Chicago.

visit the art galleries for a fun date idea in chicago
via Document

20. Take a Comedy Class at Second City

Second City is one of the premier comedy venues in Chicago and one of the most influential comedy theaters in the world. Many famous actors started out at Second City, including Tina Fey, Amy Poehler and Stephen Colbert. Taking your date to a Second City performance is one date idea in Chicago. Another is signing up for a comedy class! Second City offers many cool improv and sketch classes during weekends or evenings. 

comedy classes at second city chicago
via Second City

21. Take a Glass Blowing Class

Turn up the heat by taking an introductory glass blowing class in Chicago. A glass blowing class is one of the most fun and unique things for couples to do in Chicago. You and your date will work with a professional glass artist to create a finished product, which is sure to be a great conversation starter and memento of an epic date idea in Chicago!

artist blowing glass
via Canva

Now that you have a collection of date ideas in Chicago, you’re all ready to start planning your next adventure! Whether it’s finding your favorite slice on a Chicago pizza tour, exploring a new part of the city or taking a class together, it’s time to turn one or more of these date ideas in Chicago into reality! 

For even more fun ways to explore Chicago and beyond, check out other experiences happening on Cozymeal.

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