The buildings of Chicago are some of the most unique in the world.

A variety of cultures have influenced the way these structures were designed and built.

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

1. Shoreline Chicago Sightseeing Architecture Cruise

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

The journey starts at the Navy Pier.

It will move along the river to let you gaze at distinctive architectural marvels.

These include 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.

For the best views, try to get a seat on the roof of the cruise.

  • Departure Point:
    1: 600 E Grand Ave, Chicago, IL 60611, USA
    2: 401 N Michigan Ave, Chicago, IL 60611, USA
  • Departure Time: Boarding times between 10am-8pm
  • Duration: 1 hour

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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.

You’ll discover examples of the famed Chicago architecture.

Get to see over 50 skyscrapers that dot the city skyline.

Keep an eye out for the Trump Tower, Tribune Tower, NBC Tower, Aqua Tower, the John Hancock Building, and Wrigley Building.

Complimentary drinks, coffee, tea and cookies are included to keep you refreshed throughout the tour.

  • Departure Point: 465 N McClurg Ct, Chicago, IL 60611, USA
  • Departure Time: Boarding times between 10am-8pm
  • Duration: 1 hour 30 minutes

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3. Chicago Architectural Tour & Segway

Get to experience Chicago’s architecture on a Segway!

Save your energy and give your tired feet a rest.

Why walk when you can glide effortlessly along the riverfront of Chicago.

More importantly, you will be given a helmet and undergo thorough Segway training with the tour guide.

After that, you will go through the picturesque Grant Park and Millennium Park.

You’ll also see the Art Institute of Chicago, Chicago Water Tower, the Magnificent Mile, the Bean, BP Bridge, and more on this unique Segway tour.

Your local guide will make a number of stops to highlight the history and significance of popular Chicago landmarks.

  • Departure Point: 300 E Monroe St, Chicago, IL 60601, USA
  • Departure Time: 8:30 AM
  • Duration: 2 hours

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4. Chicago Architectural River Cruise and Helicopter Tour

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

First, your adventure starts with an unforgettable cruise.

It 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.

Hear about the Great Fire of 1871 and the architects who were responsible for making the city world-renowned for its structures.

After that, you will see Chicago from a luxury helicopter.

Go onboard a cutting-edge helicopter, giving you breathtaking views as you soar above the Chicago River and the famed city skyline.

This is ideal for couples and families who want the best VIP treatment and experience of Chicago skyline.

  • Departure Point: 1339 S Wood St, Chicago, IL 60608, USA
  • Departure Times: Between 4:40pm and 9:30pm
  • Duration: 15 to 90 minutes

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5. Chicago Walking Tour: Dazzling Interiors of the Loop

Discover the amazing interior spaces on The Loop.

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

You will be amazed at the breathtaking interiors.

An expert guide will explain the origins of the most recognised interior architecture in Chicago.

  • Departure Point: 425 S Financial Pl, Chicago, IL 60605, USA
  • Departure Time: 11:00 AM
  • Duration: 2 hours

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6. Walking Tour: Chicago Pedway System

Go on an adventure inside renowned and lesser-known Chicago structures.

Explore their stunning interiors, with the help of a guide who will keep you engaged with information about the city’s architectural marvels.

This tour will take you through about a half-mile stroll of downtown Chicago or the Loop.

You’ll see amazing structures such as a church inside a skyscraper.

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 a 50-foot tall sculpture by Picasso located at Daley Plaza.

It gets even more interesting when you go through the Chicago Pedway System.

Here you’ll see 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.

  • Departure Point: Marquette Building, 140 S Dearborn St, Chicago, IL 60603, USA
  • Departure Time: Tour sessions between 10:30am and 3pm
  • Duration: 2 hours

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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.

You’ll also see amazing structures whose interiors and exteriors reflect the Art Deco design.

This includes the Chicago Motor Club Building (which is now a Hampton Inn), the Carbide and Carbon Building, and the Century Tower.

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

  • Departure Point: Chicago Architecture Center, 111 E Wacker Dr, Chicago, IL 60601, USA
  • Departure Time: 11am
  • Duration: 1 hour 30 minutes

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8. Walking Tour: Modern Architecture

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

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

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

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

  • Departure Point: Chicago Architecture Center, 111 E Wacker Dr, Chicago, IL 60601, USA
  • Departure Time: 11:00 AM
  • Duration: 1 hour 45 minutes

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9. Land and River Chicago 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.

The tour will lead you to 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, and Jackson Park

While on the river cruise, you will have unforgettable views of over 50 Chicago skyscrapers.

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.

  • Departure Point: 30 S Michigan Ave, Chicago, IL 60603, USA
  • Departure Time: 11:30am or 3:30pm
  • Duration: 3 hours 30 minutes

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

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

You’ll go through the Loop towards the Magnificent Mile and see the Fort Dearborn Historical Site.

As the tour continues, you’ll see Wrigley Building, Tribune Tower, Wrigley Field, Lincoln Park Observatory and Zoo, and Chicago Theater.

Afterwards, you board a 90-minute architecture cruise on the Chicago River.

This will pass by magnificent skyscrapers and more historic sites.

At the end of the tour, you’ll discover why this cruise is considered by some as “the best 90 minutes spent in Chicago”.

  • Departure Point: 30 S Michigan Ave, Chicago, IL 60603, USA
  • Departure Time: 9:30am or 1:30pm
  • Duration: 3 hours 30 minutes

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11. Land and River Chicago 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.

  • Departure Point: 25 S Michigan Ave, Chicago, IL 60603, USA
  • Departure Time: 9:30am, 11:30am, 1:30pm
  • Duration: 3 hours 30 minutes

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.

  • Departure Point: any of the stops listed.
  • Duration: 2 hours

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13. 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 interiors of famed landmarks.

You’ll pass by popular landmarks such as The Willis Tower, Frank Lloyd right homes at Oak Park, the John Hancock Building, historic brownstones, and Gothic structures.

You can also enjoy a walk along the Chicago River or visit the sky decks of popular buildings.

  • Departure Point: You’ll be picked up from your centrally located hotel. If it’s a different address, you can specify the pickup point after booking confirmation.
  • Departure time: between 9am-4:30pm
  • Duration: 3 hours

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14. Chicago Architecture Centre Exhibit Admission

This admission to the Chicago Architecture Center will let you experience the city’s largest cultural organizations.

You will have access to two floors and see revolutionary exhibits.

For instance, there’s a Chicago scale model featuring 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.

Discover how Chicago earned the name, “the city of architecture”.

This is an ideal stop before or after you join a real tour to see Chicago’s landmarks.

  • Opening Hours: daily 9am-5pm
  • Address: Chicago Architecture Center, 111 E Wacker Dr, Chicago, IL 60601-3713
  • Duration: 1 hour

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15. Chicago Explorer Pass

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

You will have access to 2-5 attractions, activities, or tours of your choice.

A complete Chicago guidebook along with deals to restaurants and shops come with the package.

After visiting the first attraction included with the pass, you’ll have 30 days to see other attractions on the list, which should be plenty of time.

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!

  • Explorer Pass Inclusions: 2 to 5 attractions
  • Duration: Used within 30 days of booking

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As the birthplace of the first skyscraper in the world, the city of Chicago has grand things to offer everyone.

Any one of these tours will give you a unique perspective on Chicago’s amazing architecture, so be prepared to be blown away.

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Find More Architecture Tours in Chicago

For all new cities, I go overboard on my itinerary, just to see every major attraction. Countries I've visited include New Zealand, Singapore, Hong Kong, China, Cambodia, Japan and Thailand. Mostly Asian countries. Next target - Europe!