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Guide to Dating in Chicago – Top 10 Chicago Date Ideas

Looking for a fantastic date in Chicago? Look no further.

It’s been called “New York done right,” but most locals would argue Chicago, the third largest city in the United States, can stand on its own as a distinct metropolis. The Windy City is packed with big-city culture, gorgeous waterfront and friendly strangers, making Chicago a great place to date.

Here are a few date ideas as you navigate the Chicago dating scene.

Guide to Dating in Chicago: Laugh It Up

Chicago is the home of improvisational theater. Make your date guffaw and check out world-famous The Second City or iO Chicago Theater. Smaller comedy clubs and amateur improv troupes will make sure every night is a hilarious one.

(Tip: The Playground, Chicago’s only co-op non-profit improv group, is by-donation-only on Sundays. And it’s always BYOB.)

If Chicago’s improv scene is good enough for Tina Fey, it’s good enough for date night.

Guide to Dating in Chicago: Sweet Music

Prefer tunes to a laugh?

Live music is a great date idea in any city, but Chicago seems to have this category perfected. Chicago’s blues, soul and jazz are legendary, but it’s also the birthplace of house music and has a booming indie scene.

The Green Mill Cocktail Lounge is a favorite of trendsetters and old-school jazz aficionados. Swing music fans should stop in on Tuesday or Thursday nights. Al Capone and Charlie Chaplin used to hang out at this character-filled ex-speakeasy — not together, mind you.

Blues lovers need to visit Kingston Mines in Chicago’s North Side.

The Old Town School of Folk Music has an open house on the first Friday of every month. Bring your date and an instrument (or dancing shoes) or just sip drinks while taking in the sounds of the community.

And if you’re just looking for a little background music, head to Millennium Park for some free performances from a variety of genres this summer.

Guide to Dating in Chicago: Slam Poetry

After comedy and music, what’s next? Take your date to a poetry slam.

Check out The Encyclopedia Show at the Vittum Theatre where writers and poets create often-hilarious works on-the-spot, In-One-Ear poetry night at Heartland Cafe where local poet Pete Wolf hosts five-minute spoken-word and music performances — Hipster alert: Pabst Blue Ribbon is just $2.50 here — or the Green Mill’s famous Uptown Poetry Slam where “slam” was born.

Finger-snapping optional.

Guide to Dating in Chicago: Eat

Feed your date if you’re hoping to get a second one. Embrace your inner Chicagoan and offer to split what’s been called the city’s sauciest, doughiest, cheesiest deep-dish pizza at Giordano’s. Or pledge your allegiance to Pizzeria Uno, the inventors of the deep dish.

Not into pizza? Impress your date by reserving spots at one of Chicago’s two 3-star restaurants, Alinea or L2O.

Other date-worthy spots: Dine on Italian tapas at Quartino Ristorante and Wine Bar, share farm-to-table plates on Prasino’s great patio, or keep it casual with sandwiches at the cozy and charming Bourgeois Pig Cafe.

Foodies can walk hand-in-hand through Grant Park’s Taste of Chicago each July.

Guide to Dating in Chicago: Drink

If you’re looking for a place to go post-dinner (or instead of dinner), there are plenty of Chicago wine bars and drinking holes perfecting for getting to know someone special.

The intimate Flight 1551 is private enough to have a real conversation, and even has an outdoor patio perfect for warm summer nights. Webster’s Wine Bar, one of the city’s first wine bars, is a cozy, classic option. Or click glasses in Public Chicago’s library, which turns into a sexy lounge at night.

Become wine snobs together and sign up for a wine tasting (or winemaking) class at City Winery Chicago.

If you’re not into wine, Maude’s Liquor Bar serves great cocktails in an intimate setting.

Guide to Dating in Chicago: Get Artsy

Learning is sexy. Picnic at the 57-acre Museum Campus in Grant Park, then wander through one of the three museums on the property: the Adler Planetarium, the Shedd Aquarium or the Field Museum of Natural History.

The Museum of Contemporary Art, located downtown, boasts one of the world’s largest collections of contemporary art with almost 3,000 objects to chat about.

If your date is on a Friday, you’re in luck! On the second Friday of every month, more than 30 art spaces in the Chicago Arts District are open to the public.

Or make your own art. Unleash your inner Picasso and sip wine — yes, at the same time — at Bottle & Bottega. Or check out Unicoi art studio’s Paint the Town Bar Tour where you can enjoy a two-hour painting class at a local pub.

Guide to Dating in Chicago: Go Outside

If love is in the air, keep breathing it. Chicago’s great outdoors is, well, great. Over 552 parks comprise the Chicago Park District, 33 sand beaches welcome loungers and picnickers, and 10 bird and wildlife gardens are great for exploring with a significant other.

Visit the conservatory and lagoon at Garfield Park, enjoy a two-hour Cinderella-approved Chicago Horse & Carriage ride through Grant Park, or spend the day in Chicago’s 1,200-acre Lincoln Park. The Lincoln Park Zoo will bring out the wide-eyed kids in every love-struck couple.

Explore Old Town on foot. Check out Millennium Park at night. Or grab dessert at Anthony’s Homemade Italian Ice as you stroll through Chicago’s Lakeview neighborhood.

Dine on unique local eats and explore the city — on bike! Fork and the Road organizes culinary bike tours that make for great first dates.

Or roller-skate — hand-in-hand, of course — at The Rink.

Add a little romance and athleticism to a wintery date by lacing up your ice skates on the ice outside Wrigley Field. If you like heights, “skate in the sky” at the John Hancock Observatory, where you’ll overlook the city on the world’s highest rink.

Guide to Dating in Chicago: By Water & Sky

Explore the 156-mile Chicago River in a kayak for two. Fish from one of the city’s many park lagoons. Or head to North Avenue Beach in August for the annual Air & Water Show.

Admire the city’s great architecture from a Wednesday night boat cruise that concludes with some “oohing” and “ahhing,” thanks to front-row seats for Navy Pier’s fireworks display.

Really looking to impress? Watch the sunset from above — in a splurge-worthy helicopter ride. If you’re not up for going that high, just stick to one of the city’s many gorgeous rooftop spots: ROOF at the Wit Hotel, Terrace at the Trump, the Vertigo Sky Lounge, Zed451, or the Signature Room at the 95th in the John Hancock Center.

Keep it casual by ordering a pint on the rooftop beer garden at Gene’s Sausage Shop.

Guide to Dating in Chicago: Play Games

We rarely recommend “playing games” here on eHarmony — they rarely lead to healthy relationships — but there’s nothing wrong with a little Tetris or Clue on date night.

Bring a roll of quarters to Headquarters Beercade and challenge your date to some friendly high-score competition at this fun arcade bar. Or play old-school video games at  The Wormhole Coffee. (Featured drinks have included the Tim Curry and Thyme Warp.)

If you prefer your game-playing more low-tech, get to know your date while playing your favorite nostalgic board game at neighborhood bar Guthries Tavern.

Guide to Dating in Chicago: Cheer

Chi-Town’s sports fans are notoriously passionate. Bears fans brave the elements to cheer on their football team in the bitter cold. With two Major League Baseball teams — the Cubs on the north side and White Sox on the south side — America’s favorite pastime can be as polarizing as politics. And even when the Bulls are mediocre, you’ll spot a celebrity or two in the crowd of basketball fans.

If you don’t have tickets to the big game, find a sports bar packed with your team’s most loyal fans. Tip: Sporty dates can get loud and obnoxious. So be sure the two of you are either really good sports, or are cheering for the same team.

Guide to Dating in Chicago: Festivals

Chicago in the summer is festival-central. You’ll find a festival or fair in almost every neighborhood on every weekend from May to September.

Music fans are in heaven with Lollapalooza and Pitchfork Music Festival and the classical concert series, Grant Park Music Festival. The Ravinia Festival, in Highland Park, is the oldest outdoor music festival in the summer and hosts the Chicago Symphony Orchestra every summer.

Check out the Chicago Blues Festival in June, the Chicago Jazz Festival in August, and pick up some new moves throughout the summer thanks to one-hour dance classes at Chicago SummerDance in Grant Park.

Every fall, the Chicago International Film Festival brings Hollywood’s elite to the city Ferris Bueller called home.


Learn more about Chicago singles here.