Chicago Walking Tour with Free Rental

The perfect tour for first timers to Chicago or those who want to explore Chicago's top attractions and highlights. Stroll through the beautiful streets of downtown Chicago and learn about the City’s rich history, colorful characters, and get insider tips. Enjoy a 2hr walking tour & receive a bonus FREE 2hr bike or kayak rental, adding value to your experience. Enjoy biking along the scenic Lakefront Trail or kayaking on Lake Michigan. Bobby's Bike Hike walking tours have been recognized nationally by National Geographic, USA Today, and Conde Nast Magazine. Explore the amazing sites that Chicago made famous; Millennium Park, Chicago Riverwalk, amazing Architecture of the Wrigley Building and Chicago Theater, & Michigan Avenue dubbed ‘the Magnificent Mile’ for it’s world-renowned shopping. Bobby’s local expert guides lead you through downtown Chicago’s most iconic landmarks and share their knowledge about the City along the way. The tour covers 1.5 miles(2.25km) on easy, flat terrain.

Meeting Point

Stan’s Donuts & Coffee

750 N Rush St, Chicago, IL 60611, USA

Arrive 15 minutes early. Guide will be wearing a Bobby's Bike Hike collared polo with a branded paddle.

What's included:

• Historical stories about Chicago's past
• 2 hour Bike or Kayak Rental
• Local, Professional Tour Guide
• Walking Tour of Chicago's Top Highlights and Attractions

What to expect:

Duration: 2 hours

Historic Water Tower

806 N Michigan Ave, Chicago, 60611-2103, Illinois

The Historic Water Tower, located on Michigan Avenue, is a surviving symbol of the city's resilience, having withstood the Great Chicago Fire of 1871. Built in 1869, the limestone tower features a Gothic Revival design and stands as one of the few structures that survived the devastating fire.

10 minutes

Holy Name Cathedral

735 North State Street, , Chicago, 60654-3835, Illinois

Holy Name Cathedral in Chicago, completed in 1875, is another stunning example of Gothic Revival architecture, with its intricate spires and intricate detailing. As the seat of the Archdiocese of Chicago, the cathedral holds historical significance and is renowned for its beautiful stained glass windows and majestic interior.

10 minutes

Millennium Park

Chicago, Illinois

Millennium Park, nestled in the heart of Chicago, is a dynamic urban oasis that seamlessly blends art, architecture, and nature. Home to iconic landmarks such as the Cloud Gate sculpture and the Crown Fountain, the park offers a vibrant cultural experience against the backdrop of the city's skyline.

25 minutes

The Magnificent Mile

North Michigan Avenue, Chicago, 60611, Illinois

The Magnificent Mile, a bustling stretch of Michigan Avenue in Chicago, is a shopper's paradise and architectural marvel. Lined with upscale boutiques, flagship stores, and luxury hotels, its glittering lights and grandeur make it a captivating destination for both locals and visitors.

10 minutes

Cloud Gate

201 E. Randolph St., Millenium Park, Chicago, 60602, Illinois

Cloud Gate, known affectionately as “The Bean” debuted in Millennium Park in 2006. Designed by famed Indian artist, Anish Kapoor, this giant, stainless steel masterpiece has become one of the most famous symbols of Chicago arts and culture.

10 minutes

The Chicago Theatre

175 N State St, , Chicago, 60601-3623, Illinois

The Chicago Theatre was added to the National Register of Historic Places June 6, 1979, and was listed as a Chicago Landmark January 28, 1983. The distinctive Chicago Theatre marquee, “an unofficial emblem of the city”, appears frequently in film, television, artwork, and photography.

10 minutes

Crown Fountain

201 E Randolph St, Millennium Park, Chicago, 60602, Illinois

The Crown Fountain, a striking feature within Chicago's Millennium Park, is an interactive work of public art designed by Jaume Plensa. Comprising two towering glass block towers that display changing digital faces and spout water from their mouths, the fountain creates a unique and engaging experience for visitors, combining artistry with water elements.

5 minutes

Jay Pritzker Pavilion

Millennium Park, Chicago, Illinois

The Pritzker Pavilion, situated in Millennium Park, Chicago, is an architecturally stunning outdoor amphitheater designed by Frank Gehry. Characterized by its distinctive steel ribbons and open-air structure, the pavilion hosts a variety of cultural events and performances, providing a harmonious blend of art, nature, and innovative design.

5 minutes

Chicago Riverwalk

E. Lower Wacker Dr., Chicago, 60602, Illinois

The Chicago Riverwalk is a picturesque waterfront promenade that winds along the Chicago River, offering breathtaking views of the city's renowned architecture. Dotted with charming cafes, public art installations, and lively events, the Riverwalk serves as a dynamic hub where locals and visitors alike can soak in the scenic beauty of the city.

15 minutes

The Art Institute of Chicago

111 S Michigan Ave, Chicago, 60603-6110, Illinois

The Art Institute of Chicago is one of the oldest and largest art museums in the United States, housing an extensive collection of artworks spanning centuries and diverse cultures. Renowned for its iconic lion statues at the entrance, the museum is a cultural landmark known for its impressive exhibits, including famous masterpieces such as Grant Wood's "American Gothic" and Vincent van Gogh's "The Bedroom."

10 minutes

Daley Bicentennial Plaza

337 E Randolph Dr, , Chicago, 60602-1305, Illinois

Daley Plaza, located in the heart of downtown Chicago, is a bustling civic space known for its iconic Picasso sculpture. Surrounded by prominent government buildings, it serves as a hub for public events, farmers' markets, and features the renowned Christmas tree lighting ceremony during the holiday season.

10 minutes

Bobby's Bike Hike - Chicago Bike, Walking & Food Tours

540 N Lake Shore Dr, Chicago, IL 60611, USA

FREE 2 HOUR BIKE or KAYAK RENTAL INFO:
As an additional perk for booking this particular tour, you will get a FREE 2-hour bike or kayak rental (to be used within (+/-) 3 days of your tour booking. Terms below:
To be used within +/- 3 days of your tour booking.
Bike rentals take place at Bobby’s Bike Hike World Headquarters, 540 N. Lake Shore Drive, Chicago, IL60611. Bike shop is open year-round (excluding Thanksgiving & Christmas).
Kayak rentals take place at Ohio Street Beach, Bobby’s Kayak, 550 E. Grand Avenue, Chicago, IL 60611. Kayak shop open mid-May to mid-October, weather dependent.
Offer excludes Saturday Bike/Kayak rentals between Memorial Day (end of May) Weekend to Labor Day (early September). Kayaking only available from June-September)
No discounts for not using this activity or issues due to weather restrictions.

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