Private Chicago Highlights and Landmarks Walking Tour

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2 hours (approx.)

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Overview

Experience Chicago's best on our 2-hour private walking tour, starting at Willis Tower and ending at the Wrigley Building. Discover iconic landmarks like the Chicago Board of Trade, Cloud Gate, and the Chicago Cultural Center, alongside hidden gems. Your expert local guide will provide fascinating stories and incredible photo opportunities, making this a personalized and intimate exploration. Experience the Windy City's rich history and vibrant present with this exclusive private tour.

What's Included

Private and exclusive tour for you and your group only
Entry into multiple buildings
Professional and experienced tour guide

Meeting Location

Meeting point

South Wacker Drive
Chicago, IL 60606, 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

What To Expect

Willis Tower

The tour commences at the Willis Tower, where you will learn about its groundbreaking "bundled tube" structural system, observe its amazing facade and understand its historical significance as a former world's tallest building. Key facts regarding its immense scale and engineering will be shared, providing a foundational understanding of Chicago's leadership in skyscraper design.

5 minutes • Admission Ticket Free

Chicago Board of Trade Building (Pass By)

As we pass by the Chicago Board of Trade Building, you'll get a great view of this classic Art Deco structure at the end of LaSalle Street. Take a moment to appreciate its unique stepped design and the detailed stone carvings on its exterior, including figures that represent farming and industry. Look up to spot the famous statue of Ceres, the Roman goddess of farming, watching over the building. We'll briefly discuss its significant role in global trade and the city’s economic history as we take in this impressive sight.

Monadnock Building (Pass By)

You will see a truly unique piece of Chicago's past. Notice its very tall, dark brick walls and how solid it looks. This building is special because it shows a big change in how skyscrapers were built. One half, built first stands tall with incredibly thick brick walls. The other half, built later, used a newer steel frame hidden behind the bricks. It's a great example of Chicago's early steps in designing very tall buildings, showing both old and new ways of building in one impressive structure.

Calder's Flamingo (Pass By)

You can't miss this bright, imposing piece of public art. Notice its bold, red and orange color, often called "Calder Red," which stands out dramatically against the darker, modern buildings around it in Federal Plaza. This large, abstract sculpture is known as a "stabile" because, unlike some of Calder's other famous works, it stays still. It's a wonderful example of how art adds a splash of color and unique shape to Chicago's city landscape.

Marquette Building (Pass By)

As we pass by the Marquette Building, you'll notice another important piece of Chicago's history. This beautiful building, finished in 1895, is a great example of the early "Chicago School" style of architecture. Look closely at its detailed terracotta outside and the large windows that let in lots of light. You will see decorative panels above the entrance that hint at the building's name, honoring Father Jacques Marquette, a French explorer. It stands as a testament to the city's innovative building designs from that time

Chase Tower (Pass By)

After turning a corner, we'll briefly catch sight of the Chase Tower in the distance. Notice its distinct, gently curved shape that makes it stand out against the city's other buildings. This very tall skyscraper is a key part of Chicago's skyline, and even from here, you can appreciate its unique design as a prominent feature of the financial district,

CIBC Theatre (Pass By)

As we pass by the CIBC Theatre, you'll get a quick glimpse of one of Chicago's beautiful historic playhouses. Notice its classic theatre look, with the large marquee sign often announcing the latest big Broadway shows. This grand old building, which first opened over a hundred years ago, has been a key part of Chicago's lively theatre district for generations, bringing famous productions right here to the city.

Palmer House a Hilton Hotel

As we enter into the Palmer House, you'll see a truly historic and grand hotel, right here in the heart of the city. Notice its classic architecture that speaks to its long past. This famous hotel has been welcoming guests for well over a hundred years, and even from the outside, you can feel the sense of history and luxury that it holds within its walls. It's a real Chicago icon, known for its enduring elegance.Chocolate Brownie was created here for the World's Columbian Exposition in Chicago in 1893. Also, incredibly, the original Palmer House burned down just 13 days after it first opened in the Great Chicago Fire of 1871. Beyond its famous history, the Palmer House is also rumored to be one of Chicago's most haunted hotels. Some guests and staff have reported strange happenings, and many believe the ghost of Bertha Palmer, the hotel's original hostess, still gracefully wanders its halls, perhaps keeping an eye on her beloved grand hotel.

5 minutes • Admission Ticket Free

Adams/Wabash (Pass By)

As we continue to our next point, you'll pass directly beneath or very close to Chicago's famous "L" train tracks. Look up and you'll see the elevated steel structure, a defining feature of the downtown. You'll likely hear the rumble of a train passing overhead. This iconic "L" line is not just a way for people to get around; it's a vital part of Chicago's character and has been moving people efficiently for over a century.

Crown Fountain

You'll see two tall, fifty-foot towers made of glass blocks facing each other across a shallow pool. What makes them so special is that these towers display changing video images of real Chicago residents' faces. Watch closely, and you'll see the faces appear to spout water from their mouths. You'll learn how artist Jaume Plensa created this piece of modernity takes on old gargoyles, connecting people with art in a fun and engaging way. It's a wonderful spot to cool off, take unique photos, and simply enjoy the creative spirit of the city.

6 minutes • Admission Ticket Free

Cloud Gate

You'll marvel at Cloud Gate, known worldwide as "The Bean." As you approach this big and highly polished stainless steel sculpture by artist Anish Kapoor, you'll immediately notice its seamless, mirror-like surface. You'll discover how its curving shape reflects the Chicago skyline, the changing sky and everyone standing around it, creating fascinating, distorted images. Take your time to walk around it, step underneath its grand arch, and observe how it constantly transforms with your perspective and the light. It's one of Chicago's most iconic and beloved landmarks, offering unique photo opportunities and a truly captivating experience.

7 minutes • Admission Ticket Free

Chicago Cultural Center

Available from 8am-3:30pm (if you book after 3:30pm we will get to see the outside of the building only) Next, you'll spend some time inside the magnificent Chicago Cultural Center, often called "the people's palace." As you enter this place, which was originally Chicago's central public library, you'll immediately discover its breathtaking and ornate interior. Prepare to be amazed by its two stunning glass domes. The most famous is the Tiffany Dome in Preston Bradley Hall it's the largest Tiffany glass dome. You'll also see the beautiful dome in the Grand Army of the Republic Memorial Hall. You'll learn how this historic landmark now serves as a vibrant public space, hosting free art exhibits, concerts, and events.

20 minutes • Admission Ticket Free

Das Chicago Theatre Sign

This bright sign with its famous vertical "CHICAGO" letters, is one of the city's most photographed landmarks. You'll see how its bold design lights up the State Street, acting as a beacon for Chicago's vibrant entertainment scene. Even from the outside, you'll get a strong sense of the grandeur and history connected to the famous theatre that is a true symbol of downtown Chicago.

2 minutes • Admission Ticket Free

Jewelers Building (Pass By)

As we pass by the Jewelers Building, you'll quickly spot its very unique top! Look at the impressive green pyramid roof with its distinctive towers, making it stand out in the skyline. This grand building, finished in 1927 has a fascinating past: it was actually designed so that cars could drive directly into the building and up ramps to secure parking on upper floors.

Marina City (Pass By)

As we view the Marina City Towers from a distance, you'll immediately notice their "corncob" shape. These two 65-story cylindrical towers, completed in the 1960s, are a striking part of the Chicago skyline. You'll learn that Marina City was designed as a "city within a city," a pioneering concept that combined residential, commercial, and recreational spaces. It was also the first building in the US to use tower cranes during construction.

DuSable Bridge

As we cross the DuSable Bridge, you'll be walking over a true piece of Chicago history and engineering. This famous bridge, which spans the Chicago River, is a "double leaf bascule bridge," meaning its two sides can lift up to let tall boats pass. You'll notice the detailed sculptures on its towers, which tell stories of Chicago's early days. From here, you'll also get excellent views of the Riverwalk and the stunning buildings that line the Chicago River, appreciating its important connection to Michigan Avenue and the city's founder, Jean Baptiste Point DuSable, whom the bridge is named after.

8 minutes • Admission Ticket Free

Tribune Tower (Pass By)

As we continue, you'll spot the impressive Tribune Tower in the distance. Notice its distinct, grand Gothic-style top, with its detailed arches and pointed spires that make it look a bit like a castle. This famous building was once home to the Chicago Tribune newspaper.Even from afar, it's fascinating to know that embedded in its lower walls are actual pieces of famous buildings and landmarks from all over the world, collected by Tribune correspondents over the years.

The Wrigley Building

Our final stop will be the iconic Wrigley Building. You'll see its brilliant white terracotta exterior and its famous clock tower shining brightly, especially on a sunny day. This stunning building, built by the Wrigley chewing gum company, stands majestically at the beginning of the Magnificent Mile, acting like a grand gateway to this famous shopping street. Look at its intricate details and how it seems to glow, especially against the backdrop of the river. It's a truly elegant and recognizable landmark, leaving you with a lasting impression of Chicago's unique beauty and history.

2 minutes • Admission Ticket Free

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Additional Info

Confirmation is instant and will be received at time of booking
Service animals allowed
Public transportation options are available nearby

Suitable for all physical fitness levels
Infants and small children can ride in a pram or stroller

Frequently Asked Questions

(6)

Q: What is the cancellation policy for the Private Chicago Highlights and Landmarks 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). Read more Apr 2025