Streeterville

Just north and east of Downtown lies Streeterville. There’s nothing not to love about stunning neighborhood. This buzzing enclave is home to historic Navy Pier, the provocative Museum of Contemporary Art, and a sweeping stretch of lakefront that offers easy access to everything Lake Michigan has to offer.

Streeterville is where you’ll find Navy Pier, a family-friendly playland packed with amusement rides (including the 200-foot Centennial Wheel), gift shops and eateries, docks lined with sightseeing and cruise boats (book a lunch or dinner cruise if you can), sweeping lakefront views, summer fireworks displays, the Chicago Children’s Museum, outdoor movie screenings and live music, the Chicago Shakespeare Theater, and so much more.

Beyond the Pier, you’ll find summertime fun at Ohio Street Beach and nearby Lakefront Trail. The Museum of Contemporary Art houses innovative and experimental exhibits, featuring everyone from David Bowie to Virgil Abloh. Don’t skip the gift shop here, it’s one of the city’s best. Between sightseeing, you can treat yourself to endless dining experiences, from iconic Chicago street foods to fine dining.

Head over to the Museum of Contemporary Art’s free summer Tuesdays on the Terrace, where you can grab a drink and catch some live music. Play a round of indoor bocce ball at Pinstripes. Winter’s Jazz Club is a classic listening room where you can hear live singers six nights a week.