Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

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.

From: $0.00

Location: Chicago

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.

Community Discussion

Q&A

Q: Is there a minimum age requirement for the walking tour?

A: There's no specific minimum age for the walking tour, but the tour is generally suitable for ages 12 and up. Younger kids might find it a bit long, but they can definitely join if they're interested! Just keep in mind that the bike or kayak rentals are best for older teens and adults.

Q: What happens if the weather's bad on the day of the tour?

A: If the weather looks bad, they might reschedule your tour. You can usually cancel or rebook for a later date without any hassle, but it's best to check their policy in advance. Bring a raincoat or something waterproof, just in case!

Q: How long should I plan for parking near the tour start?

A: I'd recommend arriving at least 30 minutes early to find parking. The downtown area can be super crowded, and street parking can be tough. There are also some nearby garages, so have a backup plan just in case!

Discussions

Just did the Chicago Walking Tour and it was amazing!

I took the Chicago Walking Tour last weekend, and wow, it exceeded my expectations! Our guide was super knowledgeable about the history of Millennium Park and the art at the Art Institute. Plus, we got to kayak after the tour, which was such a chill way to see the skyline. If you're debating whether to gift this experience, I say go for it! It’s perfect for anyone who loves a mix of culture and fun.

Thinking of gifting the Chicago Walking Tour to my parents!

I'm considering giving my parents the Chicago Walking Tour for their anniversary. They love exploring new places, and this seems like a great way for them to learn about the city. Anyone know if it's suitable for older folks? I want them to have a great experience without getting too tired!