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Chicago Highlights and Attractions Walking Tour

3 Reviews 5.00 out of 5 stars Based on 3 reviews collected by City Boat Tours and TripAdvisor | Recommended by 100% of travelers | Chicago, USA

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On average, this is booked 16 (0) days in advance.

2 hours (approx.)
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Overview

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.

What's Included

  • Historical stories about Chicago's past
  • 2 hour Bike or Kayak Rental
  • Local, Professional Tour Guide
  • Gratuities
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Meeting Location

Meeting point

East Monroe Street
Chicago, IL 60603, USA

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Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

Michigan Avenue
Chicago, IL 60611, USA

Options & Pricing

Start Time • Daily 3:30 PM

What To Expect

Palmer House Hilton Historic Lobby

We’ll meet and relax in the elegantly decorated lobby of the Palmer House Hotel. You'll meet with your tour guide who will will be wearing a Bobby's Bike Hike shirt with branded paddle.
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10 minutes • Admission Ticket Free

The Art Institute of Chicago

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."
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10 minutes • Admission Ticket Free

Millennium Park

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.
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15 minutes • Admission Ticket Free

Crown Fountain

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.
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5 minutes • Admission Ticket Free

Cloud Gate

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.
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10 minutes • Admission Ticket Free

Jay Pritzker Pavilion

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.
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5 minutes • Admission Ticket Free

The Magnificent Mile

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.
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10 minutes • Admission Ticket Free

The Chicago Theatre

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.
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10 minutes • Admission Ticket Free

Daley Bicentennial Plaza

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.
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10 minutes • Admission Ticket Free

Chicago Riverwalk

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.
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15 minutes • Admission Ticket Free

Holy Name Cathedral

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.
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10 minutes • Admission Ticket Free

Historic Water Tower

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.
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10 minutes • Admission Ticket Free

Bobby's Bike Hike - Chicago Bike, Walking & Food Tours (Pass By)

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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Additional Info

  • Confirmation is instant and will be received at time of booking
  • Wheelchair accessible
  • Transportation options are wheelchair accessible
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels

Frequently Asked Questions

(8)

Q: What is the cancellation policy for the Chicago Highlights and Attractions Walking Tour?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CDT).This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund. Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

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Activity code: C-3332P28

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Reviews

5.00
3 reviews

Average 5.00 out of 5 stars based on 3 traveler reviews collected by City Boat Tours and partner sites such as Cool Destinations and TripAdvisor

5 stars
3
4 stars
0
3 stars
0
2 stars
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1 star
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On average, this is booked 16 (0) days in advance.

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What's Included

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

  • 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
  • Gratuities

What's Included

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

  • 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
  • Gratuities

Cancellation Policy

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

Free cancellation
100% refund
No refund

You can cancel up to 24 hours in advance of the tour for a full refund.

  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (CDT).
  • This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
  • This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

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American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

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