35 Incredible Date Ideas in Chicago
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 wide array of restaurants (over 7,300, according to the City of Chicago) 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 35 date ideas in Chicago.
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- Foodie Date Ideas in Chicago
- Relaxing Date Ideas in Chicago
- Free Date Ideas in Chicago
- Outdoorsy Date Ideas in Chicago
- Adventurous Date Ideas in Chicago
- Artistic Date Ideas in Chicago
- First Date Ideas in Chicago
Foodie Date Ideas in Chicago
1. Take Cooking Classes
If you and your partner are culinary enthusiasts, you’ll want to book cooking classes in Chicago for some of the best date experiences in all of the Windy City. Led by the city’s top chefs, this fun date idea in Chicago not only helps boost your confidence in the kitchen but also gives you and your date an opportunity to explore new ingredients, techniques and types of cuisine.
If you’re open to making new friends who are equally as passionate about food, book couples cooking classes in Chicago.
Maybe you’d prefer to ignite the spark of romance from your humble abode? No problem! You can choose from a wide variety of online cooking classes for an intimate date night in, during which you’ll be able to cook from the comfort of your own home!
These virtual experiences allow you to connect with the best chefs from all over the world at the click of a button.
2. Go On a Food Tour
Treat your date to a culinary and cultural stroll around vibrant and tasty neighborhoods with guided food tours in Chicago. By combining iconic food tastings of the city’s best treats with fascinating stories, local culture, history and architecture, you’ll have the perfect recipe for one of the best date ideas in Chicago. For everything from the best Wicker Park restaurants to the most popular Lincoln Park restaurants, food tours have you covered.
3. Book a Private Chef Experience
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.
4. Sip Your Way Through Winery Tours and Tastings
Embark on a winery tour or wine tasting in the city 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 idea in Chicago!
5. Share a Meal at Sun Wah BBQ
This popular eatery 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 if you have a large appetite and appreciate perfectly cooked meat.
This multi-course feast at Sun Wah BBQ 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.
6. Experience the Intrigue of 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.
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 at Geja's Café 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 delightful date idea in Chicago.
8. Grab a Chicago Hot Dog
The best date ideas in Chicago aren't always fancy, as proven by a taste of the most popular hot dogs in Chicago. These popular eats aren't just food; they're an institution.
Whether you enjoy the best hot dogs at a food festival in Chicago, one of many food halls in Chicago or simply visit your local red hot stand, finding the city's top dogs makes for a cute and laid-back date in the Windy City.
There's no pressure to impress when you're eating a hot dog. It is just one of those foods that allows you to kick back and share your thoughts, especially when enjoyed in the comfortable and welcoming environment of a spot like Devil Dawgs.
Relaxing Date Ideas in Chicago
9. Hop Online for 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 drink-mixing skills to the next level. There are also virtual wine tastings that make excellent stay-at-home date ideas in Chicago if you’d rather do less creating and more sipping.
10. Relax at AIRE Ancient Baths
Chi-Town is lucky enough to be home to a lush AIRE spa. This luxurious modern bathhouse has only nine locations worldwide, making a date here highly exclusive. Visiting this transcendent place is one of the most romantic things to do in Chicago and is also 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. Follow this self-care activity up with another relaxing date idea in Chicago, such as a massage, and you’re sure to be stress-free for many days to come.
Free Date Ideas in Chicago
11. 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 (for the city’s residents) and open year-round from Wednesdays to Sundays, making a visit to it a convenient and 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. As you may have guessed, this makes for an excellent fall date idea because of the magnificent colors that will be on display.
12. 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. This buzzing tourist attraction is home to nearly 200 unique animal species from around the world, while its landscape is bursting with the colors, textures and scents of more than 850 plant species.
13. 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.
Whether you combine this with another date night idea in Chicago, such as a booking at a restaurant, or take food with you to the festival, it’s the perfect opportunity to expand your musical horizons.
14. Enjoy the 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 an 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 films start at 6:30 p.m., so there’s more than enough time to combine this date night idea in Chicago with an early or late dinner before or after the film.
Outdoorsy Date Ideas in Chicago
15. 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 tour with Kayak Chicago.
Tour options range from an architectural journey to a sunset and city light night expedition to a happy hour excursion 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.
16. 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 magnificent museums.
If you don’t have your own set of wheels, pick up a couple of bikes from Bobby’s Bike Hike for an affordable price. There are various options to choose from, including hybrid, electric and road bikes. There are even tandem bikes available for hire to turn this activity into more of a romantic date idea.
17. 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 p.m. on Wednesdays and 10 p.m. on Saturdays, so there’s no reason not to treat your significant other to a Chicago date night taking in the magnificent colors during this show.
Adventurous Date Ideas in Chicago
18. Take a Helicopter Tour
If you’re looking to elevate your romance to the next level, a helicopter tour makes for the ultimate date night in Chicago. While daytime helicopter tours over the city will give you and your date unforgettable panoramic views of Lake Michigan, Millennium Park, Lincoln Park and Grant Park, nighttime tours give you the opportunity to soak up incredible sunsets and watch as millions of gleaming lights on hundreds of skyscrapers turn on for the night.
If you’re thinking of proposing, there are others before you who can vouch for this romantic date idea in Chicago being one of the most unforgettable ways to do it. Organize for family members and friends to meet you at your landing destination and you have the recipe for the perfect proposal.
19. 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 the city are at Dylan’s Tavern and Grill, Alhambra and The Cubby Bear.
Most salsa nights even start off with an introductory lesson, so if you’re a beginner or have two left feet, there’s no need to worry about this couples activity in Chicago, IL, not being for you.
20. Take a Dance Class
If salsa nights piqued your interest, this date idea in Chicago will more than scratch the itch. Killing three birds with one stone, this activity is a great way to burn some calories, get close to one another and let your mind work through having to learn a new routine.
There are many places to let your feet do the talking, but one of the best to go to for this Chicago date idea is Duet Dance Studio. Whether you’re looking to learn ballroom, swing or tango, amongst other dances, the teachers at this award-winning studio are eager to help you learn.
Artistic Date Ideas in Chicago
21. Tour Chicago Avenue’s Best Art Galleries
Searching for things to do in Chicago for couples that feed the mind and inspire other artistic endeavors? If you find yourself strolling between Ashland Avenue and Wood Street, you'll find some of Chicago's best galleries, providing the opportunity for a DIY art crawl. Start your tour at Western Exhibitions, then head to other local staples like DOCUMENT, Volume and the Rhona Hoffman Gallery for an artistic date idea in Chicago.
22. Take a Glass-Blowing Class
Turn up the heat and learn a new (or refine an old) skill by taking an introductory glass-blowing class in the city. This is one of the most fun and unique things for couples to do in Chicago, and you’ll end up with memorabilia that you can gift one another.
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!
23. Take a Comedy Class at The Second City
If you feel like basking in uncontrollable laughter, head to The Second City, 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 significant other to a Second City performance is a great date idea in Chicago, but if you’d like to really immerse yourself in the experience, why not sign up for a class? The Second City offers many cool workshops, ranging from improv for actors to classes that help with anxiety.
24. Take a Pottery Class
When it comes to things to do in Chicago for couples who are artistic, this one is not as easy as it looks. The good news is that Penguin Foot Pottery offers workshops for people of all skill levels. Who knows, you could be the next John Glick and you don’t even know it. If this turns out to be a fun date idea in Chicago that you’d like to make a hobby, this popular spot also offers regular classes for you and your partner to refine your skills.
First Date Ideas in Chicago
25. Browse a Bookstore
A number of Chicago bookstores still thrive in the city and offer a quiet atmosphere for conversations and browsing. If you are avid readers looking for a fun first date idea in Chicago, consider browsing the shelves of one of these gems. What a person gravitates to on the shelves is a key indicator of compatibility and can tell you a lot about your date.
Even if you’re in a longstanding relationship and you’d like to find a new book with your partner, throw in a couple of hot chocolates, and this makes for an excellent winter date idea. Check out Chicago favorites like Quimby’s Bookstore and Myopic Books in the Wicker Park neighborhood, or head to The Pile Bookstore in nearby Forest Park.
26. See a Play
With some of the best live theaters in the country, an excellent idea for a first date in Chicago is checking out a show. Theaters, both large and small, often feature discounted tickets through apps like Hot Tix and SeatGeek. Musicals, dramas and comedies are happening all year round, making them perfect Chicago first date ideas.
Check out the Lookingglass Theatre and Steppenwolf Theater, both with a long Chicago legacy and famous alumni. A quintessential Chi-Town experience, the theatre scene offers a great idea for first dates in Chicago if you’re looking to break the ice before shifting the spotlight to conversation over a meal.
27. Throw an Axe
Another adventurous first date idea if you’re in Chicago is a visit to Bad Axe Throwing in the West Loop neighborhood. Trained coaches will help guide you in your endeavors to make the perfect throw in the safest possible way. This makes for a fun Chicago date idea in winter as it takes place indoors, but this popular spot is open seven days a week during all seasons.
The company also offers regular classes to improve your skills, which makes it perfect for a scheduled date — committing to learning something new together can get sparks flying. Also, a bit of competition never hurts to amp up the chemistry. This is a fun thing for couples to do before heading to a restaurant, as you will have built up an appetite; however, Bad Axe Throwing does allow you to bring your own food if you’d prefer to do that.
28. Get Spooked
For a totally different kind of adventure, a fun first date idea in Chicago may include taking in the sights and sounds of one of the city’s great ghost and paranormal tours. These occur in a number of formats, including bus tours, walking tours and single-location haunts.
Make sure to visit Chicago spots known for spooky activity, like Downtown’s renowned Congress Plaza Hotel or Bachelor’s Grove Cemetery in nearby Midlothian, known to be one of the country’s most haunted locations.
29. Learn Archery
For more adventurous types, the city offers a number of physically engaging activities that make a perfect first date night idea in Chicago, including archery classes at the North Side Archery Club. Situated along the lake near Belmont Harbor and on Halsted Street, both clubs offer classes for all ages and various skill levels.
Classes are held outdoors along Lake Michigan during the warmer months, but indoor sessions are held at both locations during the winter months, making this a perfect Chicago first date idea year-round.
30. Browse Antiques
If you love old and beautiful things, a perfect first date idea in Chicago may include a visit to the Randolph Street Market. This buzzing attraction that runs over weekends during April and May, as well as the months of September to December, features a variety of vendors hawking old and beautiful finds in fashion, accessories, furniture and décor.
Outdoors in the summer and indoors during colder months, spend an afternoon wandering the large location and enjoying a glimpse into the past. The market is perfect for conversation as you peruse the offerings, making it a relaxed first date idea for those in Chicago.
31. Bowl a Few Rounds
If you are searching for a more laid-back idea for a good first date in Chicago, look no further than the city’s most notable bowling alley, Avondale Bowl. Different from most other bowling alleys, this is one of Chicago’s best first date spots because it has an extensive menu of drinks, including cocktails, beers and wine.
Eight lanes and a competitive spirit meet with the old-school charm of the 1950s for what promises to be a memorable Chicago date idea. Whether you are a seasoned bowler or a newbie, Avondale offers a particularly great spot for double dates and meet-ups with friends for a more casual, relaxed time.
32. Play With Dogs
If you are an animal lover, you might consider a laid-back first date visit to one of the city’s fun dog beaches. With the sand between your toes, the waves crashing ahead and your crush by your side, the coastline is one of the best places for a date in Chicago.
The largest, located at Montrose Beach on the north side, is the premier destination for local pooches and their owners to run and play in the sand. Whether you have a dog or not, the beach is perfect for getting to know each other and is a fun Chicago first date idea. Just watch where you step!
33. Walk Among Butterflies
Chicago is home to some of the best nature-focused museums in the country, including the Peggy Notebaert Nature Museum located in Lincoln Park. This picturesque locale makes an excellent idea for a first date in Chicago, offering a quiet and engaging spot to get to know your potential future partner while also learning about our natural environment.
The museum features a butterfly haven you can walk in, as well as surrounding ponds and flower gardens that make it a perfect spot to organize summer date ideas.
34. Go On a Dessert Date
A perfect way to experience the city’s eats at a lower price point is to go on a dessert date instead of a dinner one. This great first date idea in Chicago is excellent for the budget-conscious and those with a sweet tooth.
The city boasts a number of amazing ice cream spots in every neighborhood, including Lickety Split in Edgewater, Margie’s Candies in Logan Square and The Original Rainbow Cone in Beverly. For a sweet Chicago first date idea, grab a sundae or a cone and peruse the surrounding area or relax on the outdoor seating provided by dessert spots and people-watch for hours.
35. Be Amazed at Chicago Magic Lounge
With a romantic interest by your side and a talented magician in front of you, the stage is indeed set for a magical night. Head to Chicago Magic Lounge for one of the city's most popular hidden gems — literally: this retro-inspired “speakeasy” has a secret entrance.
While the allure of brilliantly crafted magic tricks will leave you absolutely bewildered, there’s more to this fun date idea in Chicago than deception. When sipping on the handcrafted cocktails and small plates of flavorful foods, you’ll realize that trickery doesn’t come only in the form of colorful balls and slight of hand deception but also in brilliant culinary craftsmanship.
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, your options are endless — be it for an initial meet-up or a 20-year anniversary celebration. 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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