Chicago Walking Tour of Highlights with Free Bike or Kayak Rental
TICKET PRICES STARTING FROM
Taxes and fees will be calculated at checkout
Overview
This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking Tour. During this 2-hour Walking Tour of Chicago, stroll through downtown’s beautiful streets as expert local guides share rich history, colorful characters, and insider tips to enhance your list of Things to do in Chicago. Your experience includes a FREE 2-hour bike or kayak rental—bike the Lakefront Trail or kayak on Lake Michigan for unforgettable skyline views. Bobby’s Bike Hike tours are nationally recognized by National Geographic, USA Today, and Condé Nast Traveler for excellence in storytelling and urban exploration. You’ll see the landmarks that define Chicago: Millennium Park, the Chicago Riverwalk, the Wrigley Building, the Chicago Theatre, and the famed Magnificent Mile. Covering 1.5 miles (2.25 km) of easy, flat terrain, this tour offers a complete and memorable introduction to the city.

TICKET PRICES STARTING FROM
Taxes and fees will be calculated at checkout
GET TICKETSTicket Options (1) Options Available
Option(s)
Chicago Walking Tour of Highlights with Free Bike or Kayak Rental
Starting from
$9.99
Ticket Information
- Mobile or paper ticket accepted
- One per booking
What's Included
- Explore Millennium Park’s iconic art and architecture with stories that reveal its deeper meaning.
- Stroll the Magnificent Mile as your guide shares the history, style, and stories behind every block.
- Discover Cloud Gate’s reflective magic as your guide reveals the meaning behind the iconic sculpture
- Enjoy a FREE 2-hour Bike Rental or Kayak Rental as an added bonus (weather permitting)
- See Chicago’s top sights up close, with rich stories that deepen every landmark you visit.
- See the Art Institute through a new lens as your guide reveals the stories behind its masterpieces.
- Walk the Riverwalk’s scenic edge as history, architecture, and culture come to life around you.
- Walking Tour of Chicago's Top Highlights and Attractions
- Your local guide brings Chicago’s stories to life with personality, insight, and charm.
- Step beneath the Chicago Theatre marquee as your guide shares the dazzling history behind its glow.
- Marvel at the Wrigley Building’s stunning architecture as your guide unveils its rich history.
What's not Included
- Gratuities
Cancellation Policy
- For a full refund, cancel at least 24 hours before the scheduled departure time.
Additional Info
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Suitable for all physical fitness levels
- TripAdvisor rated this tour its highest-level Traveler’s Choice Award each year since 2002.
- Our groups have exclusive VIP access to locations we visit.
- Operates in all weather conditions, please dress appropriately
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