At Four Seasons Chicago, you enjoy a unique vantage point from which to explore the sights, sounds and experiences around you. We hope these highlights of local attractions help simplify your planning. Please let us know how else we can assist you.
Cold Weather Activities
Chicago is not the "second city" when it comes to world class theatre. Home to the famous Steppenwolf, Lookingglass, Goodman and Chicago Shakespeare, the city has no shortage of dramatic and comedic theatre options.
Jazz and Blues
Many know Chicago as the birthplace of the blues, so it would be a miss not to visit one of the famed institutions of good 'ol blues. Kingston Mines and Buddy Guys Legends are just two of the many places to enjoy some great tunes while in town.
Second City is the name when it comes to comedy, along with IO, Comedy Bar, Zanies and the Laugh Factory. A visit to any of these venues are sure to have you laughing all night long, making for a very memorable evening in Chicago.
Chicago is the perfect destination for any sports fan. Speak to our expert Concierge team about securing tickets to a game, and make sure not to forget your lucky jersey at home.
Warm Weather Activities
Belmont Harbor Sailing
Learn to sail quickly, properly, and confidently. Chicago Sailing offers a wide range of instructional programs for beginners to experienced sailors. Sailors are welcome to rent a sailboat from our 26-boat fleet. Rentals are booked by the hour from dawn to dusk.
Lakeshore Running & Biking Path
Located east of Lakeshore Drive, the Chicago Lakefront Trail is an 18.5-mile paved trail along Lake Michigan that includes beaches, volleyball courts, playgrounds, baseball diamonds, tennis courts and soccer fields. Fitness enthusiasts can hop onto a paved path that wind throughout the park for walking, jogging or biking.
Oak Street Beach
Stroll the boardwalk of this scenic stretch, just north of the Magnificent Mile, where sunbathers, people-watchers and picnickers congregate for warm-weather fun.