During the summer, Chicago has patios, rooftops, parks, and better beaches than a Midwestern city has any right to. But during the winter, all of that outdoor fun dies off quicker than a parent in a Disney movie. That’s why we put together this list of bars with indoor activities, like bowling, skeeball, shuffleboard, and more. Because if you’re going to be drinking indoors until Mother’s Day, you might as well have something else to do besides complaining about the weather.
Game Room is on the second floor of the Chicago Athletic Association hotel and has a bocce court, billiards, foosball, darts, and board games, along with excellent cocktails and bar food like footlong Chicago dogs. It’s right across from Millennium Park and is actually kid-friendly (only until 9pm), making it the perfect place to go after they re-enact the flagpole scene from A Christmas Story with the Bean.
Everything about The Pink Squirrel in Logan Square fits into its Midwestern theme - the supper club cocktails, duckpin bowling, and all the people hiding out from the awful weather. The menu is full of the type of sweet-but-boozy cocktails your grandparents drank back in the 50s, like brandy Old Fashioneds, Harvey Wallbangers, and Grasshoppers. If you really want to go full Midwestern-dad-in-winter, they’ve got $3 cans of cheap beer. Either way, the duckpin bowling here is the best way to bowl without putting on someone else’s shoes.
There are a lot of arcade bars in Chicago (including two other Emporiums), but if you’re looking for a place to wait out a blizzard, do it at the Logan Square location. In addition to arcade games, they also have pinball, pool, air hockey, bubble hockey, foosball, skeeball, and shuffleboard. There’s also a dance floor, so if the place is empty you can always just “dance like no one’s watching” (because they’re all trapped on Lakeshore Drive).
At most breweries, the only activities are tours or having a drunken argument over whether Ben Affleck or George Clooney is a worse Batman. But Begyle Brewing in Ravenswood is a dog-friendly, BYOF taproom that’s also got skeeball. And on the weekends, they open up their second floor with more games and two sets of bags. So you can pretend you’re tailgating instead of hiding out in the attic of a brewery.
Royal Palms in Bucktown makes you feel like you’ve escaped winter by stowing away on a cruise ship. The interior looks like the lovechild of a rec center and a Tommy Bahama catalog, and they take shuffleboard seriously. There are 11 full-sized courts, and you can either get a team together for a league or (if you’ve never played before) the staff will help you with the basics. They also have food trucks and oversized board games, so even if all the courts are full, you’ll have something to do while you wait.
Unless you’re into sticky floors and dueling pianos, we wouldn’t suggest Sluggers under normal circumstances. But it’s the only bar in the city that has batting cages, and during winter this place isn’t crowded with Cubs fans. Plus, they also have air hockey, pop-a-shot, and various other games in case you swore you’d never pick up a bat again after striking out in the ninth inning of the Little League World Series.
Big Joe’s in Andersonvillie feels a little like a semi-finished basement with carpeted floors, a couple of dartboards, and a pool table the bartender will let you play for free if no one is around. But on Friday nights, they hold turtle races. There are prizes for the winner and loser of each race - and every drink you buy earns you another chance to compete. Which, obviously, is the best use of the holiday money you got from your grandparents.
If you’re at Slippery Slope on the weekend, you’re probably there to dance. But things are more laidback during the week, which means you won’t have any trouble getting a turn on the skeeball machines. And you can play for free on Mondays, which is an alright consolation for it being dark at 4pm.
Some of our favorite wintertime memories are playing Monopoly with our family, cheating just enough to win but never getting caught. Recreate this feeling at Guthrie’s in Wrigleyville - it’s a cozy bar that has everything from Parcheesi to Cards Against Humanity. With their long beer list and a BYOF policy, it’s the ideal place to spend a winter day - just don’t let your friends catch you slipping the blue $50 bills into your pocket.