Chicago has its own tempo — steady, grounded, and always moving forward. It’s a city of neighborhoods, each with its own flavor, and people who are open without being loud about it. You might meet someone playing pickup basketball at the lakefront, grabbing a beer after a street fest, or walking their dog in Lincoln Park. There’s room here to be curious, to strike up conversations, to find your crew. A shared laugh on the L, a nod across a rooftop bar — in Chicago, connection isn’t a performance. It’s real, and it’s waiting — if you’re up for it.
Share these top experiences in Chicago with someone who’s also looking to go.
Fly across the lake with Chicago Water Sport Rentals. Self-drive jet skis, city skyline in your wake, and just enough adrenaline to turn strangers into fast friends.
Work on your serve, challenge a member, or just rally in the sunshine along Lake Michigan. It’s low-key social and refreshingly unpretentious.
This Uptown jazz club is full of soul and stories. The candlelight, live music, and intimate vibe make it perfect for real conversation.
Get lost in the excitement and feel the energy of the crowd. Catching a game is the perfect environment to convert introductions into IRL experiences.
Aba Rooftop Dinner
Upscale but relaxed. A go-to spot for people who want to vibe, share plates, and not have to yell over music. Bring someone who appreciates good taste.
Finally, there’s a place where you can connect with others for the activities you enjoy without the awkwardness of dating apps or random meetups with name tags.
If you know exactly what you want to do but prefer not to go solo, there’s someone out there looking for the same experience. And if you're open to meeting new people and trying new things, we make it easy to find the right connections for exciting experiences.
