Whether you want to bike 23 miles in four hours, or simply sit back and feel the wind in your hair on a Lake Michigan boat ride, you can do it all in Chicago. Laugh, learn and even drink beer on some of our favorite tours of the city.
Faster and more fun than walking, gliding around Chicago on a Segway is a great way to visit Chicago landmarks for up-close photo opportunities. A river walk tour showcases Michigan Avenue, the Trump Tower and Wrigley Building, while a park glide tour explores Grant and Millennium Parks. $65–$100. 224 S. Michigan Ave., 312.663.0600
All ages and fitness levels are welcome on these tours, with bikes and helmets provided. Cruise the Lakefront with Bobby’s signature neighborhoods tour, or see where President Obama lives on the historic Hyde Park & Kenwood mansion tour. $45–$59. 465 N. McClurg Court, 312.915.0995
Learn about more than 82 of the city’s architectural structures and bridges from guides on these 90-minute day and night tours. Or bring a puppy on Chicago’s only canine cruise, which highlights dog-friendly hotels, restaurants and parks. $28. 112 E. Wacker Dr., 312.332.1353
Seadog Speedboat Cruises
Zoom around Lake Michigan at up to 45 miles per hour with exhilarating 360 degree spins on the 30-minute extreme thrill ride. For a more leisurely pace, the 75-minute architectural tour along the Chicago River is the only cruise to take passengers through the Chicago lock system. $22–$37. Departing from Navy Pier, 888.636.7737
Pair Chicago style hot dogs, chicken pot pie or bacon with different styles of beer while exploring lesser-known neighborhoods of Lakeview and Lincoln Park or Bucktown and Wicker Park. $59. Tours meet just off Brown or Blue line El stops, 800.979.3370
Mayhem abounds as comedienne Margaret Hicks guides guests through a series of unfortunate events in Chicago history, from the Fort Dearborn massacre to the Rush Street Bridge collapse. $20. Tour meets at corner of Wacker and Wabash, 773.593.4873