8 Chicago Spots For a Laid Back Date
Produced by The Infatuation with
Dating doesn’t have to mean hushed tones and dinner by candlelight - sometimes you just want to go somewhere for a hang out that’s less “so, tell me about your five-year plan,” and more “let’s get to know each other over a casual drink.” Together with Monkey Shoulder we’re helping you to Stick It To Stuck Up on your next date, with these easygoing Chicago spots for a non-stuffy date. Order something to eat, some Monkey Shoulder whisky to go with it, and get to know your date.
Recess is a massive restaurant and bar in the West Loop with a City Hall theme and an outdoor patio. The theme somehow works, with menus that look like municipal forms and bills that come like a parking ticket, giving you plenty of conversation starters. With a big cocktail menu, their take on a Big Mac, and a patio decked out with shipping containers, Recess is the perfect place for a Sunday daytime date.
With cheap Happy Hour specials seven days a week and a three-course prix fixe for only $35 on Sundays, Roanoke is a super solid option in the theatre district. Even though shows are back on, no one would blame you if you decided to skip the theatre and instead opt to spend some extra time getting to know your date. Try the Monkey Business (made with Monkey Shoulder whisky), instead of whispering between acts.
Rooh is a great date night spot, no matter what genre of casual date you’re looking for. This spot in the West Loop has a downstairs that’s loud and busy with plenty of atmosphere, while upstairs is quieter and better suited for conversation. Plus, the Indian food here is both attractive and, more importantly, extremely tasty.
Grapes & Grains
As the name implies, the focus at this West Loop lounge is on wine and whiskey. Alongside a big list of those two things, Grapes & Grains has a heap of space and live music Thursday, Friday, and Saturday nights.
On a quiet side street away from the action of 26th St in Little Village, Osito’s Tap has a modern speakeasy kind of feel (it did used to be an underground bookie). It’s the kind of spot where you can hang out at the bar, tell the bartenders what you’re in the mood for, and get a great cocktail out of it.
This small cocktail bar in Albany Park has a lot going on, and we like it. There’s a long drink menu of classic cocktails, signature drinks, beer, and wine, fancy bar snacks like chicken liver pate, and live DJs on the weekend. It’s a great spot for an early-in-the-game date where you’re not sure if you’ll want to leave after the first drink or stick around for food.
This Rogers Park gay bar is a true neighborhood hangout. You’ll reliably find locals here with their dogs, outdoor tables to settle in at, classic cocktails, and drink deals almost every day.
There are dates where you want to hang out in a bar and talk for three hours. And then there are dates where you need an activity. City Winery can be both. You can have a whole night here, from drinks to dinner to a live show - demonstrating your date-planning skills and figuring out whether or not either of you can sing in tune.