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Image: Time Out
Image: Time Out

The 34 best unique date ideas in Chicago

Surprise and delight your special someone with these fabulous date ideas in Chicago.

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Sometimes, the trickiest part of getting a date to be absolutely perfect isn’t just finding that special someone to share it with—it’s figuring out what on earth you’re going to do. Sure, you could go the classic route and get dinner at a romantic restaurant or see the latest blockbuster at a bougie movie theater, but why not mix it up with a truly unique date idea?

Learn more about each other while simultaneously getting the hang of a new skill at classes for every interest, or spend the day exploring each other’s musical tastes at a concert to see if you’re compatible. You also can’t go wrong just getting a drink at one of the city’s riverfront breweries or distilleries. So here are some of our favorite date ideas in Chicago to help ignite your love life.

RECOMMENDED: Check out the most romantic things to do in Chicago
RECOMMENDED: The best places to meet singles in Chicago

Time Out Market Chicago

Unique date ideas in Chicago

  • Things to do
  • Humboldt Park

Did you know that swans mate for life? You may not be trying to get hitched, but the elegant birds nonetheless make for pretty symbols of romance, especially in boat form. From May until September, you can take a swan boat for a cruise on the Humboldt Park Lagoon for $30 an hour. Paddle around for a while, then take a leisurely stroll to soak in the Prairie-style architecture of the park's historic boathouse.

  • Things to do
  • Uptown

Who needs the Westminster Dog Show when you can peep an untold number of dogs running around the beach for free? The fenced-off portion of Montrose Beach is dedicated to dogs and their owners, but we bet you and your date could pet a friendly pup or two with permission from their owners (and if all else fails, there's no harm in dog watching for a while).

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  • Things to do
  • Hyde Park

Located within the Hyde Park stretch of Burnham Park, Promontory Point—aka The Point—is a man-made peninsula that’s perfect for a multi-hour date. Arrive in the afternoon and paddle around in the lake for a while (the calmer south end is much better for swimming, FYI); as the sun begins to set, cross over to the north end and grab a seat atop the rocky seawall to gaze at one of Chicago’s best skyline views.

  • Art
  • Public art
  • Lower West Side

Stretching from the Chicago River to Western Avenue in Pilsen, the walls of an old railroad embankment host a vibrant and evolving outdoor gallery of murals by prominent and emerging artists. Impress your date by pointing out some of your favorite artworks as you move across 16th street, whether you prefer colorful creations by revered local artists like JC Rivera and Hebru Brantley or the contributions from international street artists such as ROA and Sheryo.

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  • Attractions
  • Parks and gardens
  • East Garfield Park

Looking for a cheap date idea? The Garfield Park Conservatory is free and open 365 days of the year (though you'll need to make an advance reservation and donations are welcome). You and your date can explore indoor rooms that are filled to the brim with different plant species—including palm trees, massive succulents and prehistoric ferns—or opt for a sunny for a walk among the conservatory’s 10 acres of outdoor gardens.

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  • Art
  • Galleries
  • River West/West Town

The stretch of Chicago Avenue bounded by Ashland Avenue and Wood Street is home to some of the city's best, most innovative galleries, providing the opportunity for a very manageable (and not to mention free) walking art tour. Some gallery standouts include DOCUMENT, Rhona Hoffman Gallery and Volume. When you’re done, head a bit further south off of Chicago Avenue to visit Matthew Rachman Gallery, which showcases sleek mid-century furniture and contemporary art.

  • Movie theaters
  • Independent
  • Wrigleyville

Sure, you and your date could see the latest blockbuster at the multiplex, but we think it's a little more romantic to cozy up in the Music Box's historic 750-seat theater, where you can see everything from foreign films to indie documentaries on the big screen. And if you really want to show how much you care, ask for some extra (real) butter on your bag of popcorn.

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  • Breweries
  • River West/West Town

Want to get drinks with a view? No need to shell out for pricey cocktails at a rooftop bar (unless you really want to). Instead, head to Goose Island's new brewpub at the Salt Shed, where you'll find reasonably priced ales, lagers and stouts with stunning views of the Chicago River and the sounds of live tunes from the music venue.

  • Interactive
  • Uptown
  • price 1 of 4

Plays can be overlong and stuffy and comedy shows occasionally fall flat—instead of taking your chances, strike a happy balance between the two at The Neo-Futurist Theater in Andersonville, where the Neo-Futurists have been redefining the parameters of live theater for more than 30 years. The troupe's signature show, The Infinite Wrench, packs 30 miniature plays into one 60-minute performance, to absurd, hilarious and oftentimes touching effect.

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  • Shopping
  • Music and entertainment
  • Lower West Side
  • price 2 of 4

You don't have to enjoy the same music as the person you're dating, but it helps to have a few genres or bands in common. Stock up on some tunes that you can listen to together at 606 Records, where you'll find classic rock and soul LPs alongside releases from adventurous local and international labels. Perhaps a Numero Group compilation or a Mr Bongo reissue could be the perfect soundtrack for your next dinner?

  • Things to do
  • Sport events
  • West Loop

Axe throwing has surged in popularity over the past couple years, but don't discount it as a novel (if slightly intense) date option. Bring some snacks and non-alcoholic beverages along to lighten the mood as you test who has the better arm, and be sure to visit the Bad Axe Throwing's website to check for walk-in availability.

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  • Seafood
  • South Deering
  • price 1 of 4

What's more romantic than traveling to the edge of Illinois to enjoy some smoked fish from this beloved shack? Calumet Fisheries has been serving catfish, shrimp and salmon for more than 70 years. It's a takeout-only business, so you'll need to grab your brown paper sack of grub and find a spot to share it, whether in your car or on the 95th Street bridge that famously appeared in The Blues Brothers.

  • Cocktail bars
  • Lake View

When grabbing cocktails starts to feel passé, consider getting a little more creative with your date night imbibing. The groovy, '70s-inspired digs of Koval Distillery's Ravenswood tasting room offers a perfect venue for sampling the distillery's small-batch spirits, which you can order in flights to maximize tasting potential. Settle into one of the bar's overstuffed leather couches and choose from a selection of whiskey, gin or interestingly-flavored liqueurs (including rosehip, coffee, chrysanthemum and honey).

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  • Attractions
  • Sightseeing
  • Lincoln Square

You could sit around and idly chat with your date or you could get some exercise and see some beautiful scenery along the way. The North Shore Channel Trail follows the Chicago River north to Evanston, with plenty of worthwhile stops along the way. Depending on how far you're willing to go (you'll probably make it farther on a bike), you could swing by Lincolnwood Town Center, admire the art at Skokie Northshore Sculpture Park or end up at the Bahá'í House of Worship in Wilmette.

  • Shopping
  • Thrift stores
  • Avondale

Find a new outfit or browse used books together at this beloved Avondale thrift store, where proceeds benefit addiction recovery, and those experiencing homelessness. Show up ready to find some deals on all sorts of gently-used items, or if you’re really passionate, get involved by volunteering at the store and sorting and organizing donations.

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  • Attractions
  • Arcades and amusements
  • Avondale

Though walk-ins are technically available, you're much better off making a reservation for you and your date to play a few rounds at this retro-looking bowling alley in Avondale, which fills up pretty fast on nights and weekends. You'll need to do some basic math when you bowl—there isn't a computerized scorecard in sight here—but the vintage vibes (and the well-stocked bar in back) are well worth the trouble.

  • Shopping
  • Bookstores
  • Hyde Park
  • price 2 of 4

If you're way past the introductory questions (Where are you from? What do you do? What's your family like?), enjoy each other's silence at 57th Street Books in Hyde Park. The sprawling but cozy shop is lauded for its noteworthy selection of local authors, so go page through some tomes together and try not to silently judge what you each decide to purchase.

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  • Things to do

Did you know that you can take in masterpieces at the Art Institute of Chicago and gaze at tropical fish while strolling through Shedd Aquarium without spending a dime? With a little planning and some research, Illinois residents can enjoy free museum days at some of the city's top institutions. Browse upcoming free days or visit an always-gratis museum or zoo whenever you please.

  • New City

Trying to impress an eco-friendly date? On select Sundays, the folks at The Plant—a former meat-packing facility in Back of the Yards that's now home to a coterie of sustainability-focused food businesses—offer a tour of the building's facilities, providing a behind-the-scenes perspective on its model for reducing waste. Reserve your tour spot online and stick around afterwards for a free tour of Whiner Beer Company.

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  • Nightlife
  • Uptown
  • price 2 of 4

Pay homage to Chicago's magic-steeped history at this Ravenswood lounge that boasts three performance spaces including the performance bar, the Blackstone Cabaret mainstage and the intimate 654 Club. The interactive performers will have you and your date laughing in no time, easing those early-date jitters.

  • Health and beauty
  • Massage and body treatments
  • Streeterville

It’s fun to be on-the-go during a date, but sometimes it’s even more fun to just relax. There are few places better to fully treat yourself than a spa, and the Four Seasons Hotel is an ideal place for you and your date to unwind with a couples massage or get pampered separately and bond over how great you feel afterwards. The Four Seasons Hotel spa offers six different massage options, as well as facial treatments like the Black Diamond Facial, which, as its name suggests, literally uses diamond particles. When you’re done, take a dip in the spa’s 44-foot-long waterfall-edge indoor pool.

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  • Things to do
  • Lake View

Even if your date seems perfect on every level, if they aren’t into your pet cat, it’s never going to work out. Test out your kitty compatibility at The Catcade. Make a reservation at the Logan Square arcade-themed cat rescue, and have fun playing with the felines. Who knows, maybe you’ll even fall in love there? If it’s not with your date, it could be a new kitten that will never leave your side instead.

  • Shopping
  • Wicker Park

There are few things that are as romance-inducing as candles. So why not learn to make one while trying to find love? Bring your date to a candle-making class at Wicker Park’s Black Luxe Candle Co. Classes last for an hour, and they need another hour afterwards to set before they’re ready to take home, leaving you and your date more time to get to know one another.

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  • Music

You don’t have to have everything in common with the person you’re dating—in fact, that would be kind of weird. But you should be compatible on some fronts, like music for example. Test that compatibility at any of the city’s dozens of music venues, or if you’re looking for an exciting date night on a budget this summer, you’re in luck. All summer long, the Millennium Park Summer Music Series is hosting free concerts, with performances from GZA, Corrine Bailey Rae and more.

  • Ice cream parlors
  • Logan Square
  • price 1 of 4

Many great dates end with dessert, so end yours with some of the city’s best at Margie’s Candies. The retro ice cream parlor and diner has been delighting sweet lovers on Western Avenue for more than a century. Don’t hesitate in trying one of the parlor’s massive ice cream sundaes, but maybe hold off on the 25-scoop one until you’re on a double, or quadruple, date.

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  • Art
  • Sheffield & DePaul

Maybe you’re not skilled enough at pottery—yet—to be as romantic as Patrick Swayze and Demi Moore in Ghost, but that doesn’t mean you can’t still have a fun time learning the ropes of the art form together. Park West Ceramics in Lincoln Park offers beginner and advanced-intermediate classes, as well as handbuilding classes and one-day workshops on most Fridays and Saturdays.

  • Things to do

If you’re hoping to cling to your date a little tighter, maybe a scary story could help make that happen. Head out on a ghost tour together, and learn about some of Chicago’s most frightening tales—from the Lincoln Park alley where notorious bank robber John Dillinger was gunned down to the ghosts that supposedly haunt the halls of the Congress Hotel. There are numerous ghost tours throughout the city, including a monthly ghost tour pub crawl, so you and your date can grab a drink during and afterwards. Even if you don’t get spooked, you’ll spend the tour learning interesting stories about the city’s history.

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  • Things to do
  • Literary events
  • Woodlawn

You might not be able to fly your date all the way to Tokyo (yet), so do the next best thing and spend some time walking through the city’s Japanese Garden together. The gardens are located on the southwest side of Jackson Park, and were first established for the World’s Columbian Exposition in 1893. Every spring, the garden is filled with beautiful cherry blossom trees—but it’s wonderful to visit through all the other seasons as well.

A bit of friendly competition can bring out the best in you and your date, if done correctly. Should you be competing over things like jobs or money? No. But should you compete to see who is the best at arcade games? Absolutely. See if your date is up to the challenge at one of Chicago’s many arcade bars, like Logan Arcade and Emporium Arcade Bar, which has three locations across the city. With dozens of iconic ’80s and ’90s games and pinball machines, like Street Fighter, NBA Jam and Frogger, there’s plenty of fun, nostalgia and competitive spirit to go around.

 

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  • Things to do
  • Festivals

Chicago is home to a vast amount of festivals throughout the summer, but some of them can cost a small fortune. Thankfully, there’s plenty more that cost nothing at all, taking the financial stress out of a date. Bring a romantic partner to one of the city’s many free summer festivals, like the 57th Street Art Fair, where you can peruse work made by hundreds of artists, or Chicago Summerdance, where you and your date can pick up a few moves at the months-long series that offers free dance lessons. There’s plenty of free music festivals as well, like the Chicago Jazz Festival, which brings in legends of the genre. Cap off your free festival experience with a bite to eat at the Taste of Chicago, the world’s largest food festival, which has been running for more than 40 years.

  • Sports and fitness
  • Baseball & softball
  • Wrigleyville
  • price 1 of 4

In Chicago, a lot of people’s first love is their favorite sports team—whether that’s the Cubs, Blackhawks, White Sox, Bears, Bulls, Fire or Red Stars. Of course, they also can make room in their hearts for another special person. But why not combine the two loves by planning a date at one of the city’s stadiums, arenas and fields, like Wrigley Field or the United Center? Conveniently, there’s something to see all year long, and tickets at all price points (especially if the team isn’t doing so well). Win or lose, it’s bound to be a fun time.

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  • Pubs
  • Wrigleyville
  • price 1 of 4

It’s not a unique date idea to go grab a drink at a bar, but a night at Guthrie’s Tavern certainly could be. The Lakeview watering hole has a full bar with a lengthy beer list, and also something that makes it distinctive: An endless supply of board games. The selection includes classics like Monopoly, Connect Four and Clue, and there's even board game leagues for serious competitors. If games aren’t your thing, stop by for one of Guthrie’s Tavern’s other events with your date, like Tuesday night trivia, or free donuts on the weekends.

34. Hit the (miniature) links at Big Mini Putt Club

Unless you and your date are passionate about the sport, playing a full round of golf can be pretty draining as it take a long time to complete. Instead, play a round of mini golf at Big Mini Putt Club, a nine-hole mini golf venue that has locations in Lakeview and Lincoln Park. The course is indoors and has locally-themed holes, like the Wrigley Field hole, where players have to navigate past three different bases to make their putt. Big Mini Putt Club also features a full bar featuring cocktails, beer, wine and non-alcoholic drinks.

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