The Pink Squirrel
Bar · Logan Square
2414 N Milwaukee Ave, Chicago, IL 60647
Highlights
Retro cocktails, boozy milkshakes, and duckpin bowling await
Retro cocktails, boozy milkshakes, and duckpin bowling await
"The Pink Squirrel’s theme is “Midwestern culture,” but unlike your uncle from Wisconsin whose hobbies are watching the Packers and drinking in the garage, this place isn’t boring. For example, there’s duckpin bowling and events like trivia night. Plus, this place has a drink menu that includes non-alcoholic versions of cocktails like Grasshoppers, along with milkshakes. And in case you don’t feel like standing all night watching people bowl, this place has plenty of diner-style booths that make it easy to get a seat. Another thing that’s easy? Beating drunk people at bowling." - adrian kane
"The Pink Squirrel’s theme is “Midwestern culture,” but unlike your college roommate from Green Bay with a cheese wedge hat, this place is actually very cool. They serve retro drinks you’ve probably heard of but might not have tried (like Harvey Wallbangers), along with things like gimlets and Old Fashioneds. The space is low-key, and has plenty of diner-style booths that make getting a seat pretty easy. There’s even duckpin bowling, which is a great way to strike up a conversation. You won’t even need to wear hideous shoes." - adrian kane
"When you’re ready to be reminded even further that you’re in the Midwest, just head southeast on Milwaukee until you hear the sound of tiny bowling balls hitting tiny bowling pins. That’s when you’ll know you’ve reached this cocktail bar designed to feel like a supper club/bowling alley. Come for a Wisconsin Old Fashioned (made with brandy), and follow that up with a milkshake and some duckpin bowling." - adrian kane
"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." - josh barnett
"We’d come to The Pink Squirrel for the supper club cocktails like Rob Roys and Harvey Wallbangers alone. But it’s also got two duckpin bowling lanes, which make for a nice change of pace from the more party-forward bars on this strip of Milwaukee. When you throw a strike with a brandy Old Fashioned in your hand, you’ll feel like the ultimate Midwesterner—now all you need is an Urlacher jersey and the number of a good basement waterproofer." - josh barnett, john ringor
