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
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.
If Chicago’s improv scene is good enough for Tina Fey, it’s good enough for date night.
Guide to Dating in Chicago: Listen
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.
Guide to Dating in Chicago: Words
Take your date to a literary reading or poetry slam. There’s something for everyone, whether it’s The Encyclopedia Show at the Vittum Theatre where writers and poets create often-hilarious works on-the-spot, the punk-rock reading Neutron Bomb at Cal’s Liquors 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.
Foodies can still hand-in-hand through Grant Park’s Taste of Chicago each summer.
Guide to Dating in Chicago: Cultured
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.
Art connoisseurs and art-appreciators alike should stroll through the River North neighborhood with their dates. Here you’ll find the country’s second-largest concentration of contemporary art galleries. 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.
Guide to Dating in Chicago: Keep It Natural
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.
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.
Guide to Dating in Chicago: The Water
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.
Guide to Dating in Chicago: Skate
Tired of walking? Skate! Roller-skate — hand-in-hand, of course — at The Rink. Or 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: Play
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.
Every fall, the Chicago International Film Festival brings Hollywood’s elite to the city Ferris Bueller called home.
Learn more about Chicago singles here.