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Photograph: John Khuu

The 21 most interesting date ideas in Chicago

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

Written by Erin Yarnall in association with Vizzy Hard Seltzer
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Summer in Chicago has arrived, and we hope your love life is heating up just as fast as the balmy weather! Still, whether you’re navigating a flirty new fling or hoping to ignite sparks in a long-term relationship, planning a date isn’t easy—and while there are plenty of romantic restaurants in Chicago for wining and dining your SO, sometimes it’s nice to break the dating mold with something a little more out of the box. Need romantic inspiration? Allow us to be of service. From quiet afternoons at the best art galleries in Chicago to rollicking rounds of axe-throwing, here are some of our favorite ideas for creative dates throughout Chicago for relationships, situationships and everything in between.

RECOMMENDED: Check out the most romantic places in Chicago


Time Out Market Chicago
  • Restaurants
  • West Loop

It's hard to agree on a place to eat at any stage in a relationship, so why not make date night as simple as possible? If you want sushi and your partner wants pizza, that's something that Time Out Market Chicago can provide. With some of the best chefs in the city serving food out of 18 kitchens, there's something for nearly every taste, whether you're in the mood for tacos, ramen, fried chicken or ice cream. Order a meal, grab some drinks and let the conversation flow.

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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  • Things to do
  • Lincoln Park

You won't find many better venues for a first date than Lincoln Park Zoo, which is A.) Free to enter and B.) Full to the brim with things to talk about when conversation starts to falter. Point out pygmy hippos and polar bears in between exchanging getting-to-know-you niceties—and if things progress smoothly, you can always keep the night going at a nearby bar. 

  • 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. Start at Matthew Rachman Gallery, which showcases sleek mid-century furniture and contemporary art, then head due west. You'll find other gallery standouts like DOCUMENT, Rhona Hoffman Gallery, Volume and more along the way. Just keep in mind that many galleries are requiring reservations in advance of your visit.

  • 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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  • Bars
  • Breweries
  • Avondale

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 Metropolitan Brewing, where you'll find reasonably priced German-style beers with stunning views of the Chicago River just outside of its Avondale taproom. 

  • Theater
  • 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 company's website to check for walk-in availability at either of two Chicago locations.

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  • Restaurants
  • 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.

  • Bars
  • 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 new 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.

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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 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.

  • Restaurants
  • New City

Trying to impress an eco-friendly date? Every Sunday, the folks at The Plant—a former meatpacking 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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