17 Best Chicago Architecture Tours

The buildings of Chicago are indicative of a colorful melting pot, with a variety of cultures influencing the way these structures were designed and built.

Check out this list of the best Chicago architecture tours to experience the remarkably unique styles that dot the city’s skyline.

1/ Shoreline Sightseeing Architecture Cruise

Go on a cruise down the Chicago River and learn more about the city’s renowned architecture and history from an expert architectural guide.

The journey starts at the Navy Pier and will move along the river to let you gaze at distinctive architectural marvels such as the Aon Center, the IBM Building, the Wrigley Building, Willis Tower (also known as the Sears Tower), John Hancock Center, and more.

You will also get to see structures designed and built by legendary architects, such as Helmut Jahn, Skidmore, Owings and Merrill (SOM), and Mies van der Rohe.

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2/ Chicago Architecture Foundation Center River Cruise on First Lady

Join this 90-minute architectural cruise that will take you down the Main, North, and South branches of the Chicago River on your way to discover examples of the famed Chicago architecture.

You will get to see over 50 skyscrapers that dot the city skyline, including the Trump Tower, Tribune Tower, NBC Tower, Aqua Tower, the John Hancock Building, Wrigley Building, and a whole lot more.

Complimentary Coca-Cola drinks, Starbucks Coffee, Twinings tea, lemonade and cookies are included to keep you refreshed throughout the tour.

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3/ Chicago Segway Art & Architectural Tour

Get to experience Chicago’s architecture on a Segway!

Save your energy and give your tired feet a rest from all the walking you’ve done around the city as you glide effortlessly along the riverfront.

You will be given a helmet and will undergo thorough training with the tour guide for safety reasons, prior to the actual tour.

You will go through the picturesque Grant Park, Millennium Park, the Art Institute of Chicago, Chicago Water Tower, the Magnificent Mile, the Bean, BP Bridge, and more on this unique Segway tour.

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4/ Architectural River Cruise and Chicago Helicopter Tour

Grab this chance to see Chicago’s legendary architecture from the water, and from the air.

Your adventure starts with an unforgettable cruise which will take you through all three branches of the Chicago River to see the famed architectural landmarks of the city.

The 75-minute cruise includes a narrative from your professional guide on how the city was reborn after the Great Fire of 1871, as well as information about the architects who were responsible for making the city world-renowned for its structures.

You will then get to see Chicago from up above, onboard a cutting-edge helicopter, giving you breathtaking views as you soar above the Chicago River and the famed city skyline.

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5/ Walking Tour: Dazzling Interiors of the Loop

Discover the amazing interior spaces that you otherwise wouldn’t be looking at in the city’s central business district, The Loop.

This walking tour takes you inside buildings to give you a chance to see the architectural wonders hidden by the hustle & bustle of the downtown area.

You will be amazed at the breathtaking interiors that are just waiting to be explored, with the help of an experienced tour guide.

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6/ Walking Tour: Chicago Pedway System

Go on an adventure inside renowned and lesser-known Chicago structures to explore their stunning interiors, with the help of an expert guide who will keep you entertained with fascinating information about the city’s architectural marvels.

This tour will take you through about a half-mile stroll of downtown Chicago or the Loop, where you can see amazing structures such as a church inside a skyscraper and take a peek at the awe-inspiring atrium ceiling designed by Tiffany & Co at the former Marshall Field and Company Building.

The tour will also pass by the majestic yet untitled 50-foot tall sculpture by Picasso located at Daley Plaza.

It gets even more interesting when you go through the Chicago Pedway System, which is a series of climate-controlled skybridges, passages, and underground concourses that keeps the downtown buildings connected to one another.

The journey ends at the city’s first central public library built in 1897 – the Chicago Cultural Center.

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7/ Walking Tour: Art Deco Skyscrapers

Relive a time of style and glamour as you discover the role that Chicago played in the Art Deco design style’s international movement.

See amazing structures whose interiors and exteriors reflect the Art Deco design, such as the Chicago Motor Club Building (which is now a Hampton Inn), the Carbide and Carbon Building (now the location of the St. Jane Hotel), and the Century Tower (what used to be the Trustees System Service Building).

Experience the cool sophistication of the eclectic Art Deco movement with this 90-minute walking tour!

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8/ Walking Tour: Modern Architecture

This tour takes you on an adventure to discover some of the city’s (and the world’s) most spectacular examples of modern architecture.

These buildings are characterized by a lack of ornamentation, technical precision, and an evident structure.

Gaze at legendary skyscrapers by pioneers of the Modernism movement, such as Bertrand Goldberg, Ludwig Mies van der Rohe, and Harry Weese.

Some of the famous Chicago landmarks you will encounter include the Daley Center, Marina City, and the IBM Building.

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9/ Chicago Land and River Architecture Tour: Historic South Side

Go on this architectural tour that lets you discover Chicago’s famed structures on land, and from the water.

Explore the landmarks that dot the city’s historic South Side, which will take you to see the Art Institute of Chicago, Grant Park, the starting point of Route 66, the site of Chess Records, President Obama’s home, the Museum of Science and Industry, Jackson Park, and more.

While on the river cruise, you will have unforgettable views of over 50 skyscrapers that make up the iconic Chicago skyline.

You will learn more of the city’s history, including how it rose from the ashes in less than 10 years after the Great Chicago Fire with spectacular architectural powerhouses.

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10/ Chicago Land and River Architecture Tour: Scenic North Side

Explore the city’s beautiful North Side on the land tour of this land-and-river architectural adventure.

Go through the Loop towards the Magnificent Mile, and see the Fort Dearborn Historical Site, Wrigley Building, Tribune Tower, Wrigley Field, Lincoln Park Observatory and Zoo, passing by the L Train, onto the Chicago Theater.

The 90-minute architecture cruise on the Chicago River takes you to gaze at magnificent skyscrapers and historic sites from your unique vantage point on the river.

Discover why this cruise is considered by some as “the best 90 minutes spent in Chicago”.

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11/ Chicago Land and River Architecture Tour: North and South Shores

Get to see the best of Chicago in terms of architecture on this tour which takes you to the North and South Sides of the city –including a scenic river cruise.

This comprehensive tour will quench your thirst for the most stunning examples of iconic, historic, and modern architecture.

You can look forward to seeing renowned landmarks on the North Side such as the Millennium Park, Wrigley Building, Wrigley Field, and Tribune Tower.

Explore the South Side’s architectural wonders, including the Art Institute of Chicago, Grant Park, University of Chicago, Robie Park, Museum of Science & Industry, Jackson Park, Buckingham Fountain, and Museum Campus.

This adventure includes a 90-minute cruise on the Chicago River, where you can admire more than 50 awe-inspiring skyscrapers from the water.

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12/ Chicago Big Bus Hop on Hop off

Create your adventure and set your own pace as you explore Chicago on the Big Bus hop-on hop-off tour.

The double-decked, open-decked bus is the ideal way to get acquainted with the city and see the architectural landmarks up close and personal.

The bus stops are located near 14 of the most popular tourist attractions, so you are sure to see iconic structures as you go around the city.

The full circuit of the bus will take about 2 hours to be completed, but you have the flexibility of hopping on and off the bust as many times as you want to.

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13/ Chicago Trolley Hop on Hop off

See the magnificent structures that dot the Chicago landscape on a hop-on hop-off trolley tour of the city.

You can set your own pace and choose a pass that offers between 1-3 days of unlimited boarding and hopping off the trolley, which also includes a local expert giving a riveting narrative of the city’s history.

The 12 stops are located in strategic points close to tourist attractions, so you will have a chance to explore most of the city’s iconic architectural landmarks.

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14/ Willis Tower Skydeck, Trolley Tour and Chicago River Cruise

Treat yourself to a VIP tour that will take you to see the majestic architectural structures of Chicago.

Get express entry to the Willis Tower (formerly known as the Sears Tower) where you will quickly have access to the Skydeck on the 103rd floor without the huge crowds.

You will then take an adventure while riding a classic Chicago trolley that will breeze through Field Museum, John Hancock Center, and Millennium Park.

This VIP tour ends with a cruise on the Chicago River, where you can enjoy an afternoon view of the iconic skyscrapers while enjoying your complimentary drink.

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15/ Private Chicago Architecture Tour

Enjoy a more personalized view of the city by going on this private architecture tour.

This includes a chauffeured luxury vehicle and a local tour guide who is an expert on Chicago architecture.

Get to see the magnificent exteriors and in some instances, the interiors as well of famed landmarks such as The Willis Tower (formerly known as the Sears Tower), Frank Lloyd right homes at Oak Park, the John Hancock Building specific points on the Magnificent Mile, historic brownstones, and Gothic structures.

You can choose to include more stops including a walk along the Chicago River, and going on famous skyscrapers’ observation or sky decks.

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16/ Chicago Architecture Centre Exhibit Admission

This admission to the Chicago Architecture Center will give you the chance to experience being part of one of the city’s largest cultural organizations.

The admission voucher gives you access to two floors of revolutionary exhibits, including a Chicago scale model which features 4,250 buildings, an interactive Chicago City Model Experience, and supersized scale models of renowned skyscrapers.

Visit the Chicago Gallery to see the city’s captivating housing styles and neighborhoods, and discover how Chicago earned the moniker, “the city of architecture”.

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17/ Chicago Explorer Pass

Take advantage of this multi-attraction pass to create your own personalized itinerary of exploring Chicago.

You will have access to 3-5 attractions, activities, or tours of your choice

You have 30 days from your first use to go through the things you have chosen (valid for 1 year after purchase).

Take your pick from over 25 activities and sites that include the top attractions in the city like entry to Willis Tower and the Architecture River Cruise.

This is the most affordable and convenient way to explore Chicago at your own pace!

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As the birthplace of the first skyscraper in the world, the city of Chicago has grand things to offer everyone who comes to visit and explore its architectural wonders.

Be prepared to be blown away by the magnificence of the structures you will encounter, as you go on the best eye-opening architecture tours in the Windy City.

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