There's a lot of the great outdoors you can explore in the Windy City.

BY WATER

Chicago Architecture Foundation River Cruise
If there's one "must-do" while in Chicago, it's this tour—a 90-minute cruise down the Chicago River that uncovers the history of the city's magnificent architecture.

Chicago River Canoe and Kayak
Want to do your own exploring down the Chicago River? Rent a canoe or kayak (or sign up for a guided tour).

Chicago Sailing Club
If you're an experienced sailor looking to explore new waters, or want to take a fireworks cruise—the Chicago Sailing Club will help you sail along the shores of Lake Michigan.

 

BY LAND 

Lakeshore Trail
Fishing, birdwatching, biking, running, beach volleyball, paddle boating, or skateboarding—you can find it all along Chicago's Lakeshore Trail, which has easy access from the Guesthouse via Foster or Lawrence Avenue.

The 606
Chicago's newest park system, The 606 is a former elevated train rail turned walking, running, and cycling path, that connects 2.7 miles of Chicago with four neighborhood parks from Wicker Park to Humboldt Park. Access the trail by hopping on the Damen bus (25 minute ride) and getting off at Churchill Park.

Chicago Park District
From yoga on the beach to movies in the park, there's always a chance to enjoy fun in the sun or under the stars in Chicago—and for little to no cost!