Unusual Date Ideas to Try in Chicago, IL

The Date Night Throw Down pottery workshop is a fun, unique date idea in Chicago.
The Date Night Throw Down pottery workshop is a fun, unique date idea in Chicago. | © Kate Bek Photography / Courtesy of Lillstreet Arts Center
Sarah Ashley

In a Tinder and Bumble landscape, courtship can get repetitive. For anyone interested in mixing things up or testing what a potential mate is really made of, we invite you to try out these unusual date ideas in Chicago. Only one result is guaranteed: It won’t be boring.

Did you know – Culture Trip now does bookable, small-group trips? Pick from authentic, immersive Epic Trips, compact and action-packed Mini Trips and sparkling, expansive Sailing Trips.

Toyota Park

Chicago is well-known for its sports teams. But instead of hitting up a Bears or Bulls game, we recommend heading out to Toyota Park to watch the Chicago Fire, the Windy City’s Major League Soccer team. The Fire, named after the infamous blaze that burned through Chicago in 1871, won U.S. Open Cups in 1998, 2000, 2003 and 2006. They also won the MLS Cup in 1998, their debut season. Toyota Park is located in the historic Bridgeview neighborhood on Chicago’s South Side and has 20,000 seats. The Chicago Red Stars (National Women’s Soccer League) also play here, as do the Chicago Bliss (Legends Football League).

The iFly experience gets your blood pumping and adrenaline kicking. With locations all over the world, this organization makes skydiving possible without an airplane. The company has developed a method of simulating a realistic skydiving experience inside a compact chamber. Using wind tunnel technology, you and your date can have a safe flight without worrying about parachutes, altitude or the inconvenience of having to jump out of an airplane. This is a perfect date option for couples looking for a physical rush and a hilarious photo opportunity that involves body suits, helmets and goggles. (Flyers must be 13 years old and weigh under 260 lbs.)

Chicago Magic Lounge

An ode to Chicago-style magic, the Chicago Magic Lounge in Andersonville hosts some of the city’s best and brightest magicians. Practicing bar and restaurant magic has been a tradition in Chicago since 1915. Couples can sit back and relax with cocktails and snacks in the luxurious Blackstone Cabaret as magicians perform sleight-of-hand tricks right at their tables before the main event begins. There are four additional areas to visit inside the Chicago Magic Lounge, including a magician’s library. Romantic red velvet curtains, dim lighting and secret doors add an air of mystery.

The Chopping Block

Engaging in any activity that requires hand-eye coordination is an entertaining way to get to know someone new, or discover an unexpected skill in a longtime love. The Chopping Block, a cooking school and shop for all things culinary, offers classes and workshops in everything from sushi to bread baking. The company hosts date night, couples cooking and happy hour classes, plus a Bloody Mary brunch workshop on Saturdays for sweethearts looking for weekend activities. With locations in both River North (at the Merchandise Mart) and Lincoln Square, The Chopping Block is a solid option for beginner and intermediate cooks looking to up their game and try something fun.

Free Tours by Foot

Anish Kapoor’s Cloud Gate, popularly known as the Bean, is one of the iconic attractions in Chicago

Free Tours by Foot is the go-to site for anyone itching to get outside, take photos and learn something new. Packed with options for foodies, architecture buffs, ghost enthusiasts and more, there’s a tour for everyone. If you know your new partner is obsessed with Hollywood, we suggest embarking on the “On Location: Movies and Filming in Chicago” tour, which takes groups to famous sites from Ferris Bueller’s Day Off, The Fugitive and Blues Brothers, just to name a few. Most tours are pay-what-you-can, so this is a terrific option for couples looking to save some cash for a deep-dish pizza after a long day of walking.

SPiN Ping Pong

Do you and your sweetie enjoy getting competitive, either with each other or against other couples? Then you’ve got to visit SPiN Ping Pong in River North. This dual late-night bar and ping pong playground offers club membership for serious players and casual walk-ins every night of the week. They serve up great eats and host weekly tournaments and live music. During the summer months, SPiN has a patio area complete with ping pong tables. The venue hosts events like charity fundraisers, happy hour festivities, Cinco de Mayo taco-eating contests and more.

Half Acre Beer Company

With one location in Chicago’s North Center neighborhood and another in West Edgewater, Half Acre Beer Company is on a roll. Taking a tour of their taproom is definitely our idea of a fun and unique date. Every Saturday at 11 a.m., for only $10, you and your partner can get behind the scenes at Half Acre’s breweries. That entry fee gets you on a tour, three samples of craft beer and a branded pint glass to take home. Can’t make it on a Saturday? It’s still worth a trip to try your own flight of beers any other day of the week. Half Acre is the brainchild of founder Gabriel Magliaro, who set up the company in 2006. Initially contract brewed out of a brewery in Wisconsin, Half Acre established its current brew house in 2009. The venue offers four year-round beers, complemented by a number of seasonal and one-off brews.

Ballroom Dance Chicago

Is there a better icebreaker than dancing? Ballroom Dance Chicago is a fun, energizing date idea for new couples and seasoned partners alike. At this top-rated Chicago studio, couples can sign up for lessons leading up to their wedding day, and pairs/singles just looking to mingle and move can sign up for BYOB classes. The BYOB classes in Salsa, Swing and Ballroom are held during weekday evenings and on Saturday afternoons. Swapping partners during these classes is encouraged to create a friendlier atmosphere, but you’re not obliged to do this. The studio has a roster of professional dance instructors and full-time wedding prep pros. Grab a bottle of wine and head over to their main studio in Ravenswood, or the smaller studio location in the West Loop.

The Dinner Detective – Chicago

Unlike most murder mystery dinner theater, The Dinner Detective hides its actors in the dining room posing as real people alongside the guests. So, if you and your date are interested in participating in a goofy yet macabre event, you’d best sign up for a night out at this dinner theater. Throughout the evening, guests eat dinner as a mystery unfolds. A detective in full costume leads the audience (and hidden players) through uncovered clues, hijinks and hilarious interviews to figure out who the ‘killer’ is. If a guest guesses the murderer correctly before the night is done, they take home a prize. The Dinner Detective is the perfect night out for couples who fancy intrigue, problem-solving and good old-fashioned mystery.

Underground Donut Tour

Forget lunch dates. Spend a weekend morning with your sweetheart tasting samples of the best donuts in Chicago! For a flat fee of $30, Underground Donut Tour offers a two-hour excursion through Chicago’s Loop to four different delicious donut shops. Donuts are included in the ticket price, though of course patrons are invited to bring extra cash in case something tastes so good, they want more. This is a prime opportunity to find out if you and your partner both enjoy savory-sweet maple bacon donuts, or if one of you can’t get enough of Do-Rite Donut’s lemon pistachio. It’s also a great way to see Chicago’s exquisite architecture when the sidewalks downtown aren’t crowded with weekday foot traffic. Tours are held all year, weather permitting.

Lillstreet Art Center

Located in Ravenswood, the Lillstreet Art Center offers classes and workshops for people of all ages. With 20 classrooms, state-of-the-art equipment and a full roster of professional instructors, it’s hard to go wrong when choosing a workshop. We recommend starting with a bite at First Slice, a café on the center’s first floor, before crafting. Then, head up to Date Night Throw Down, a pottery workshop designed for couples or pairs. After you and your date create magnificent artwork, visit the gift shop across from First Slice to check out the gorgeous items made by students and professional artists.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

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