There’s nothing wrong with a packed bar or a big night out, but sometimes you just want to sit somewhere comfortable and have a conversation without competing with the music. Not every night out needs a packed dance floor or a plan that sends you racing across the city and Chicago has plenty of places that make slowing down feel like the whole point. Here are some of the best spots and experiences for a more intentional night out in Chicago.
Break bread with friends and strangers at a supper club
A supper club is made for taking your time. With a set menu and everyone settling in for the same experience, dinner is the main event. The intimate nature of supper clubs are what make them so special, giving you the chance to break bread with strangers and let the conversation unfold. Some of our favorites include those hosted by Duck Sel, Haru Haru, and Txa Txa Club.
Listen intentionally in intimate spaces
Carefully chosen records, warm acoustics, crafted cocktails and comfortable seating create a special social space. Tune in and talk between tracks, properly enjoying what is playing rather than treating the music as background noise. Charis Listening Bar is a go to spot, while Parachute HiFi often host listening nights where staying for one more drink feels like the obvious choice. For something a little more off the beaten track, dorian’s is a lively cocktail bar hidden behind a record store, hosting its B.Y.O.V. (Bring Your Own Vinyl) night every Tuesday alongside vinyl DJs throughout the week.
Swap small talk over bar snacks for something worth chewing over
Had enough of the same old small talk? For a night out that gives you something more interesting to talk about, Big Questions, Cool Drinks brings thought-provoking science to the night out. Over 60 minutes, this immersive event brings cutting-edge brain science out of stuffy academic halls and into the accessible, relaxed setting of The Den Theatre. Here you will meet curious people, Expect an accessible expert-led discussion, a drink in hand, and plenty of space to ask questions without the atmosphere ever feeling like a boring lecture.
Give the group chat something worth discussing
The city’s book clubs are an easy way to make plans with friends who are often hard to pin down. Choosing the same book gives everyone a common starting point, so the conversation is already waiting when you arrive. Whether the club you join meets in a café, bar, or independent bookstore, it is an excuse to swap opinions, hear different perspectives, and spend the evening talking about something with a little more substance. Check out Silent Book Club or Chicago Book and Sip Club, which both hold monthly meet ups in initiate bars and venues.
