From the iconic skyline along Lake Michigan to the buzz of Wicker Park, dating in Chicago is all about variety. Whether you’re catching a baseball game or grabbing cocktails in a hidden speakeasy, there’s no shortage of date ideas. But what makes Chicago such a great place to find love?
As part of our “Find Me on Bumble” campaign, we asked our community—Chicagoans who know their neighborhoods inside and out—for the best local spots. They told us what dating is actually like in the Windy City, giving you everything you need to make your next outing one to remember.*
Favorite date ideas in Chicago
Whether it’s a bookstore in Bucktown or a night at a jazz club in Uptown, our community has the scoop on the off-the-beaten-path locations that will make your date stand out.
Q: What’s a hidden gem you’re obsessed with?
BRIDGET: There’s this amazing little community coffee shop called Kusanya on the corner of 69th in Englewood. And don’t miss A Listening Space at 305 E Garfield—it’s one of those places that has this energy you just can’t find anywhere else.
JOSH: The Green Mill in Uptown is the ultimate jazz club—it’s like stepping into a time machine, but with a drink in hand. I also love Garfield Park Conservatory. It’s like a tropical escape right in the middle of the city.
EMILY: Oh, there’s so much to love! Kibbitznest is this quirky little bookstore/coffee shop/bar combo—it’s perfect for a chill date. And Bourgeois Pig is a must—it’s this cozy coffee shop during the day, but at night, it turns into a full-on Gatsby-inspired speakeasy. If you’re into sweets, Windy City Sweets and Margie’s Candies are both great, and North Buena Deli is where I go for any sandwich cravings.
Q: Favorite first-date spot?
BRIDGET: If I’m in the mood for some Southern comfort food, Virtue Southern Restaurant never disappoints. And Harold’s Chicken on 87th—don’t sleep on it. It’s a Chicago classic. If I want to feel fancy, Soho House Chicago and The Hoxton Hotel are my go-to spots. And for something super casual, Carver 47 and Dan Ryan Grill always have a welcoming atmosphere.
EMILY: A walk around the Lakefront Trail is always a good idea. For a fun night, Zanies is my comedy club of choice, and Topo Gigio right across the street is perfect for a post-laugh Italian meal. Oh, and I can’t forget about Philz Coffee—my regular stop. For a chill bar vibe, Halligans and Wills Northwoods Inn are great.
Q: Favorite neighborhood?
BRIDGET: My favorite neighborhood has got to be Bronzeville. It’s on the South Side, and used to be home to the largest Black-owned bank, rivaling the Harlem Renaissance in terms of cultural impact. Right now, there’s this incredible movement to bring that energy back. Bronzeville’s got amazing food, the Defender building, and some of the most beautiful Greystones (buildings are made of limestone or gray sandstone) lining King Drive.
JOSH: I’ve got a soft spot for Old Town. It’s one of those neighborhoods that’s got a little bit of everything—great food, cool bars, unique restaurants, and theaters for when you want to see a show—all within walking distance.
What to expect when dating in Chicago
From local artists showcasing their work in Pilsen galleries to foodies hunting down the best deep-dish pizza, Chicago is full of people with passions. Here’s what our community has to say about dating in the city:
Q: Finish the sentence: Chicago is the only place where….
BRIDGET: Chicago is the only place where you can walk into a hole-in-the-wall restaurant and walk out with a Michelin-star experience. The city’s food scene is a vibe.
JOSH: Well, it’s the only place I want to be right now. You get the best of both worlds: the excitement and diversity of a big city with the community feel of a smaller one.
I love every part of Chicago—the things I’ve learned, the places I’ve been, and all the adventures I’ve still got ahead.
Q: How would you describe dating in Chicago?
BRIDGET: Like going to the movies, but you think you’re in for one thing, and then—plot twist—you end up staying for the movie even though it’s totally not what you thought it would be. You just have to roll with it!
JOSH: Like dating in four different cities. Seriously, every part of the city has its own vibe—whether it’s the people, the food, or the activities. The seasons make everything feel different too, so you’re never really in the same place twice.
From the buzzing nightlife of River North to the artsy vibe of Logan Square, Chicago has a rhythm that’s totally its own. Whether you’re into late-night spots or local music scenes, there’s always something new to check out—and with Bumble, you can find someone who’s down to discover the city with you.
*We are not affiliated with, endorsed by, or connected to any companies, locations, or brands mentioned in this article. All statements listing any as such are in the opinion of our interviewed users. All company, location, and brand names are trademarks of their respective owners.