Give your group a unique Chicago experience by arranging an active outdoor tour of the city. Get around on foot, bicycle, Segway, or kayak and see Chicago from a new perspective while getting plenty of exercise.
Walking tours
View amazing public art on the Loop Mural Walk with a step-by-step, self-guided itinerary created by the Chicago Loop Alliance. Use a smart phone to follow one or all three routes leading to over 20 colorful murals — some whimsical and others thought-provoking — by both local and well-known artists.
Explore Chicago with Free Tours by Foot. Groups can go on a guided walk to destinations like Millennium Park, the Loop, the Chicago Riverwalk, Lincoln Park, and The Magnificent Mile. For creepy fun, try the Chicago Ghost Tour. Free self-guided tours are available using information provided by Free Tours by Foot’s guides. Customized private tours can be arranged for your group.
Take a 60-minute walk with Pilsen Public Art Tours and discover murals reflecting over 50 years of neighborhood history. Veteran guide Luis Tubens leads the trek for groups of up to 35 with routes taking visitors by the National Mexican Museum of Art, Pilsen Arts and Community House, Ashland Avenue, and along 16th Street. Mural art styles include traditional, graffiti, and pop art.
Choose from popular walking tours that include the viewing of art deco skyscrapers and must-see landmarks along the Chicago River on excursions offered by the Chicago Architecture Center. Listen as certified docents share anecdotes about the historic buildings. Book a private group tour and receive discounted pricing for 20 or more participants.
Group members can see the city on their own with a Chicago Greeter tour. This free, year-round service customizes outings to individual interests. Local volunteer guides lead the way to neighborhoods, attractions, and hidden gems. Tours can accommodate up to six guests. Register at least two weeks in advance. Foreign language tours are available based on request and volunteer availability.
Bike and Segway tours
Pedal with your group along The 606, an elevated trail that was once an abandoned railway. The scenic 2.7-mile (4.3-kilometer) route crosses over street-level parks and neighborhoods that include Bucktown, Logan Square, Wicker Park, and Humboldt Park. Several Divvy stations offer affordable bike rentals. The 606 is also great for walking and running.
Bobby’s Bike Hike offers guided bike tours that have been recognized on best-of lists curated by USA Today, Tripadvisor, and Entrepreneur magazine. Travel along the lakefront, across the city, through neighborhoods, and to Chicago eateries. Itineraries for private group bookings can be customized. Bobby’s also offers walking, food, kayak, and stand-up paddleboard tours.
Rent rides at Bike and Roll Chicago’s Navy Pier or Millennium Park locations. Choose from guided Segway or bike tours that focus on the city’s history, famous buildings, lakefront, and neighborhoods. Private tours can be arranged.
Glide along city streets on an e-bike or Segway with Absolutely Chicago Segway Tours. Groups can follow the Lake Michigan shoreline to Grant Park, the Museum Campus, Northerly Island, and many other attractions. An entertaining option is the two-hour Insider Segway Tour that focuses on wacky and weird stories about Chicago. Small and large groups can book private tours.
Fitness and water tours
Combine exercise and sightseeing with Fit Tours Chicago. Take the Downtown Chicago Highlights Running Tour or embark on the Chicago River Yoga Walk. Fitness professionals lead the exercises while sharing their city knowledge. Private group bookings can accommodate from 10 to 150 people.
Take a guided tour with Urban Kayaks from its lakefront or Chicago Riverwalk locations. Book a group of up to 12 people for the popular two-hour Historic Chicago tour, traveling 1.5 miles (2.4 kilometers) down the Chicago River to Wolf Point. Six or more people can join the Skyline Paddle tour that follows the perimeter of Monroe Harbor for stunning city skyline and Museum Campus views.
Discover more Chicago tours.
