Best of Chicago History & Architecture Walking Tour

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Highlights

Small group (max 10 people)
Visit Millennium Park to see Cloud Gate Sculpture and Crown Fountain
Walk Along historic Magnificent Mile
Visit Chicago Pedway
Great view of Lake Michigan Along the Chicago River Walk
Visit Navy Pier
Pass several points of interest including Starbucks Reserve Roastery, Chicago Riverwalk, Tribune Tower and Wrigley Bridge

Summary

Join our Best of Chicago Walking Tour through the city's vibrant heart, from the bustling Navy Pier to the iconic Cloud Gate, topped off with the option to enjoy a classic Chicago savory treat and visit the Starbucks Reserve Roastery. Discover architectural wonders and rich history in this immersive tour that blends urban charm with cultural vibrancy.

Tour info

Duration

2 hours 30 minutes

Group Size

Pricing (From)

Adult: (13-99 years)

$49.99

Child: (4-12 years)

$39.99

Infant: (0-3 years)

$10.00

Dropoff location

Navy Pier, East Grand Avenue, Chicago, IL, USA

Why take this tour?

Embark on an exciting walking tour through the heart of Chicago, where each step unveils the city’s rich history and vibrant culture.

Start your journey at Millennium Park, where you'll marvel at the famous Cloud Gate, affectionately known as "The Bean” setting the perfect stage for a day filled with fascinating stories and stunning sights. As you wander through the park, enjoy the lush gardens and captivating public art that make this space a true urban oasis.

Next, explore the hidden gems of the Chicago Pedway, a network of underground walkways that offer a unique perspective on the city’s infrastructure.

Emerging onto the scenic Chicago Riverwalk, you'll be treated to breathtaking views of the river, lined with some of Chicago's most impressive skyscrapers.

Continue your stroll along the Magnificent Mile, where history and modernity blend seamlessly. Admire the elegant architecture of the Wrigley Building and the Tribune Tower, and take a moment to appreciate the grandeur of the John Hancock Building.

As you cross the historic Michigan Avenue (DuSable) Bridge, you’ll feel the city’s vibrant energy all around you. Dive into the history of the Chicago Fire and the resilient spirit that rebuilt the city, and then indulge in some of Chicago’s iconic foods.

Next, have the opportunity to enjoy a classic Chicago savory treat (not included in the price) and visit the renowned Starbucks Reserve Roastery, savoring the flavors that are as rich as the city’s heritage.

Conclude your tour with a visit to more landmarks along the Magnificent Mile, including the beautiful Tribune and Wrigley buildings.

As you conclude this comprehensive exploration, you'll gain a deeper understanding and appreciation of Chicago's vibrant spirit and timeless charm.

What’s included?

Small group (max 10 people)
Millenium Park to see Cloud Gate Sculpture and Crown Fountain
Local Guide
Gratuities (optional)
Chicago Dog (add on)

Things to know

Before you book

Small group (max 10 people)
Moderate Amount of Walking (Approx. 3 miles)

Before you go

Exact tour length may vary slightly depending on individual walking speeds
Tour will operate rain or shine. We recommend dressing for the weather and comfortable footwear. You may also wish to bring water
Please arrive at the meeting location 10-15 mins prior to the start time of the tour
Appropriate footwear and water is recommended

Cancellation Policy

Full refunds will be offered for cancellations made at least 24 hours prior to departure time. For cancellations made with less than 24 hours to departure time, a $50 cancellation fee per guest will apply.

Operator Website

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About operator:

Tripshepherd specializes in offering intimate small-group tours across popular destinations in North America. Our commitment to small-group dynamics ensures a more personal connection, greater flexibility, and an escape from the hassle of crowded buses and the need for microphones. At the heart of our tours are local experiences; we proudly hire local guides to support community growth, create jobs, and provide our guests with an authentic glimpse into each destination. Our friendly guides are dedicated to connecting personally with each guest, ensuring a caring and memorable experience. With Tripshepherd, every journey is not just a tour, but a unique story woven into the fabric of local life, guaranteeing an authentic, personal, and local adventure.