Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

5.0

based on 5 reviews

| Chicago, United States

Features

Free Cancellation

For a full refund, cancel at least 24 hours before the scheduled departure time.

Instant ticket delivery

Mobile Ticket

Pickup available

Duration

2 hours

Wheelchair accessible

Audio guide

Live guide

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.

Gratuities

Mobile or paper ticket accepted
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

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...

Duration 2 Hours
Group Tour
Max 18 people in the group

1
Millennium Park
Millennium Park is one of the city’s most captivating stops on our Chicago Walking Tour, a centerpiece of your Walking Tour of Chicago designed to showcase the city’s most iconic Top Attractions and unforgettable Highlights. Your guide shares insider stories about how this award-winning public space transformed from industrial rail...
- Duration 15 Minutes•
- No Admission Ticket Required
2
The Magnificent Mile
The Magnificent Mile is one of the most iconic stretches you’ll explore on our Chicago Walking Tour, a vibrant stop on any Walking Tour of Chicago showcasing the city's most impressive Top Attractions and urban Highlights. As you stroll this world-famous avenue, your guide shares insider stories about how Michigan...
- Duration 10 Minutes•
- No Admission Ticket Required

Chicago Riverwalk

The Chicago Riverwalk is a standout stop on our Chicago Walking Tour, an essential moment on any Walking Tour of Chicago that highlights the city’s most scenic Top Attractions and memorable Highlights. As you stroll along the waterfront, your guide shares insider stories about how this vibrant promenade transformed a...

Duration 15 Minutes•
No Admission Ticket Required

Crown Fountain

Crown Fountain is one of the most captivating stops on our Chicago Walking Tour, a guest favorite on any Walking Tour of Chicago featuring the city’s most innovative Top Attractions and memorable Highlights. Your guide reveals insider stories about how this groundbreaking art installation by Jaume Plensa blends technology, architecture,...

Duration 5 Minutes•
No Admission Ticket Required

The Chicago Theatre

The Chicago Theatre is a showstopping highlight on our Chicago Walking Tour, a must-see stop on any Walking Tour of Chicago featuring the city’s most iconic Top Attractions and cultural Highlights. Standing beneath its glowing marquee, your guide shares insider stories about how this 1921 French Baroque masterpiece became the...

Duration 10 Minutes•
No Admission Ticket Required

Historic Water Tower

The Historic Water Tower is a defining stop on our Chicago Walking Tour, an essential feature of any Walking Tour of Chicago highlighting the city’s most enduring Top Attractions and architectural Highlights. As one of the few structures to survive the Great Chicago Fire of 1871, this limestone landmark stands...

Duration 10 Minutes•
No Admission Ticket Required

Cloud Gate

Cloud Gate, affectionately known as “The Bean,” is one of the most iconic stops on our Chicago Walking Tour, a marquee moment on any Walking Tour of Chicago featuring the city’s most celebrated Top Attractions and unforgettable Highlights. Your guide shares insider stories about how artist Anish Kapoor designed this...

Duration 10 Minutes•
No Admission Ticket Required

The Art Institute of Chicago

Experience the world-renowned Art Institute of Chicago on our Chicago Walking Tour, a centerpiece of your Walking Tour of Chicago designed to showcase the city’s most iconic Top Attractions and cultural Highlights. As you approach the museum’s grand entrance, you’ll be greeted by the famous bronze lions—symbols of Chicago’s artistic...

Duration 10 Minutes•
No Admission Ticket Required

Holy Name Cathedral

Holy Name Cathedral is an inspiring stop on our Chicago Walking Tour, a meaningful addition to any Walking Tour of Chicago showcasing some of the city’s most memorable Top Attractions and architectural Highlights. As you approach its striking Gothic Revival façade, your guide shares insider stories about the cathedral’s early...

Duration 10 Minutes•
No Admission Ticket Required

Jay Pritzker Pavilion

The Jay Pritzker Pavilion is a standout stop on our Chicago Walking Tour, a highlight of any Walking Tour of Chicago featuring the city’s most impressive Top Attractions and cultural Highlights. Your guide shares insider stories about how architect Frank Gehry designed its flowing steel ribbons to merge sculpture, architecture,...

Duration 5 Minutes•
No Admission Ticket Required

Daley Bicentennial Plaza

Daley Bicentennial Plaza is a peaceful yet fascinating stop on our Chicago Walking Tour, an often-overlooked gem on any Walking Tour of Chicago featuring the city's most inviting Top Attractions and scenic Highlights. Your guide shares insider stories about how this quiet corner of Grant Park once served as the...

Duration 10 Minutes•
No Admission Ticket Required

Palmer House Hilton Historic Lobby

xperience the elegance of the Palmer House’s historic lobby on our Chicago Walking Tour, a signature stop on your Walking Tour of Chicago that reveals the city’s Top Attractions through rich stories and unforgettable Highlights. Step beneath the shimmering Tiffany-designed ceiling—one of the largest of its kind in the world—and...

Duration 10 Minutes•
No Admission Ticket Required

North Lake Shore Drive

FREE 2 HOUR BIKE or KAYAK RENTAL INFO:
As an additional perk for booking this particular Chicago Walking 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...