9 Great Chicago Architecture Tours

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If you’re looking for the best Chicago architecture tours, you’ve found them here! As a local who has explored these tours on weekends, during staycations, or while showing visiting friends around Chicago, I can honestly say that this list shares the most unique and fun experiences.

The city has great options including the best architectural boat tours, helicopter tours, walking tours, and more.

If you have limited hours, take the Hop On/Hop Off bus tour in Chicago or visit the top Chicago attractions to get the most out of a short amount of time. Real all about this in this roundup post!

Best Chicago Architecture Tours

Chicago Architecture Cruise

If you love touring on water, then this cruise is for you. I’ve taken this cruise several times while showing friends the city and they loved it too.

On this cruise, you will ride the Chicago River and see the city’s famous architecture. You’ll see the impressive flat skyline including over 40 famous buildings such as Navy Pier, the Wrigley Building, and the John Hancock Building with audio narratives. The tour covers all three branches of the Chicago River.

Navy Pier Centennial Wheel Regular & Express

This is one of my favorite ways to see the city and the Chicago skyline. You circle only once, but the ride is super slow, and you’ll have some great photo ops when you get to the top.

Navy Pier is among the most visited destinations in the world. It offers beautiful views from the wheel, and it’s a must-do when in the area! Located right on the pier, you have spectacular views of the city’s skyline, architecture, and waterfront.

45-Minute Private Helicopter Flight

I was scheduled to go on this flight but it was canceled due to bad weather. At least they are good at following safety protocol. Too bad that I missed this amazing experience by helicopter. From what I hear, you will get the best views of touring Chicago architecture, and the experience of flying amongst the clouds. 

woman in Skydeck

Willis Tower Skydeck and The Ledge

Having been on the Skydeck a couple of times, it never disappoints. What I didn’t like much was that there is a limited time that you have to stand in the box. But if there were no supervision, the line would be from the street.

But here, you will have some of the most breathtaking views of Lake Michigan. You’ll also see why home is to beautiful parks and cultural attractions such as the Adler Planetarium, Millenium Park, the Shedd Aquarium, and Grant Park.

Look north to see Chicago’s iconic skyscrapers and landmarks from Lincoln Park to the world-famous Wrigley Field.

Night Tour with Willis Tower Entry & Skyline Cruise

This tour is a wonderful way to spend the evening while touring in Chicago. You’ll immerse yourself in one of the tallest architectural buildings in Chicago along with a Chicago boat tour. 

Experience the Windy City’s most popular attractions on this overnight tour. Watch the night light show of Buckingham Fountain. Cruise along the Chicago skyline and climb to the top of the iconic Willis Tower.

Big Bus Panoramic Sunset Tour with Live Guide

If this is your first visit to this city, this is a great way to tour Chicago, Illinois and how it shines at night. There is so much to see on both sides of the bus since the architecture of Chicago is interesting.

Experience the stunning skyscrapers of Windy City that light up at night. Take a panoramic nighttime tour from the Magnificent Mile to Michigan Avenue past the Chicago Theater and Buckingham Fountain.

Chicago History, Culture, and Architecture Walking Tour

This is a great way to hear about Chicago’s history and architecture. Take a private stroll or share walks with family or friends for this architecture tour. You can see old and new architecture, try delicious local treats, see beautiful boats tour the river. 

I also recommend visiting the Jane Addams-Hull House Museum for a firsthand experience of the artifacts and memorabilia that tell the story of this pivotal institution for social reform.

Chicago Architecture Center Exhibit Admission

The Chicago Architecture Center or CAC is located at the south end of Magnificent Rock near Michigan Walker Intersection. You’ll discover super-sized models of architecture from around the world.

The vouchers give you access to two floors of imaginative exhibitions at the city’s newest cultural venue.

Chicago Art Deco Skyscrapers Walking Tour

The luxurious materials and geometric decorations of Art Deco represent the opulence and optimism of the decadent 20s. Visit some of the city’s most beautiful architecture and learn about the history and characteristics of this modern decorative style.

Final Thoughts on the Best Chicago Architecture Tours

These are the best ways to tour Chicago architecture and see all the unmissable attractions. I’ve taken almost every single one of these tours, including ones not mentioned and found them worth the money.

I enjoyed seeing the towering skyscrapers and iconic landmarks. The tours offer a fascinating glimpse into the architectural history of the Chicago. Not to mention, it’s nice to play tourist in my own back yard.

As a visitor, be sure to plan your tour in advance and consider factors such as weather and time of day to make the most of your experience. Don’t forget your camera to capture the stunning views along the way.

Whether you’re an architecture enthusiast or simply looking to appreciate the city’s remarkable skyline, a Chicago architecture tour is a must-do activity. The buildings are inspiring structures, and some are a marvel of innovative designs that have shaped this iconic city.

Whether you go on water, in the air, or on foot, book your tour today and embark on a journey through Chicago’s architectural wonders.


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