Chicago: Best of Attractions Walking Tour +Bike/Kayak Rental

Chicago Guided Walking Tour with Free Bike or Kayak Rental

Experience a 2-hour guided walking tour in downtown Chicago, ideal for visitors interested in architecture, history, and city landmarks.

Highlights

• Visit key Chicago sites including Chicago Theater and the Wrigley Building
• Explore Millennium Park and see Cloud Gate (the Chicago Bean)
• Walk along Michigan Avenue, known as the Magnificent Mile
• Learn from a local expert guide about Chicago's history and current events
• Receive a free 2-hour bike or kayak rental to use within three days of your tour

Description

Join a 2-hour guided stroll through Chicago’s central landmarks, featuring architectural highlights such as the Magnificent Mile and the Chicago Theatre. The tour includes visits to Millennium Park, the Chicago Riverwalk, the Art Institute, and the Cloud Gate sculpture.

This award-winning walking tour is accessible to all fitness levels and offers an informative overview of the city’s history and culture. During colder months, the tour includes the underground Pedway system for warmth, while warmer seasons allow street-level exploration.

After your tour, enjoy a complimentary 2-hour bike or kayak rental. Bike along Chicago’s 20-mile Lakefront Trail or kayak on Lake Michigan at Ohio Street Beach. The bike rental operates year-round, while kayak rentals run mid-May to mid-October, weather permitting.

Free 2-Hour Bike or Kayak Rental Information

• Valid within +/- 3 days of your tour booking
• Bike rentals at Bobby’s Bike Hike Headquarters, 540 N. Lake Shore Drive, Chicago, IL 60611 (open year-round except Thanksgiving and Christmas)
• Kayak rentals at Ohio Street Beach, Bobby’s Kayak, 550 E. Grand Avenue, Chicago, IL 60611 (available mid-May to mid-October, weather dependent)
• Bike and kayak rentals are not available on Saturdays between Memorial Day weekend and Labor Day; kayaking is only available June through September
• No refunds or discounts if unable to use rentals due to weather

Includes

• Local, professional guide
• Entry to all included sites and attractions
• Free 2-hour bike or kayak rental (weather permitting; see details above)

Excludes

• Guide gratuity (15-20% suggested)

Important Information

• Arrive 15 minutes early for check-in; tours operate rain, shine, or snow—dress accordingly
• Suggested gratuity for the guide is 15-20%
• Bike rentals at 540 N. Lake Shore Drive; kayak rentals at 550 E. Grand Avenue (addresses above)
• Free bike or kayak rental terms apply as noted

Cancellation Policy

Cancel up to 24 hours in advance for a full refund.

Book in advance and plan to bring comfortable walking shoes, weather-appropriate clothing, and a valid ID for bike or kayak rental pickup.