Although Serena could work on her form, we love playing pickleball with friends.
Just north in Bucktown/Wicker, this is the ultimate spot for indoor driving range sessions with a full bar and kitchen.
Famous for "the best burger in America." Pro tip: the wait is long, so put your name in and grab a drink at Lone Wolf next door.
Head downstairs to their basement "Library" for velvet booths and a moody, candlelit drink.
Fresh, handmade pasta you can watch them roll through the window.
Tucked inside a record store (no, seriously), this is a "through-the-back" jazz and cocktail lounge.
Our favorite Thursday night hangout spot.