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My Walking Tours of Chicago’s Art and Architecture

Amy French the Roaming Historian

Chicago is a city resplendent with renowned architecture, fabulous art, lovely parks, good food, neat history, and fine culture. The architectural history of Chicago is relatively recent—even for an American city—since the Great Fire of 1871 destroyed over three miles of the city and over 17,000 structures. Architects though rebuilt the city giving us a city caught in the time of the Industrial Revolution and one preparing to be a leading U.S. city. They succeeded. Chicago even captivated the heads of the 1893 Columbian Exposition drawing the world’s fairs to its Lake Michigan shoreline.

Some of the world’s greatest architects, such as Daniel Burnham, Louis Sullivan, Sophia Hayden, Frank Lloyd Wright, Holabird & Roche, and John Root all left their mark on the city. I enjoy walking around the city and letting architectural treasures unfold. But for those who would like a more pointed route, I’ve created several walking tours around different sectors of the city.

Chicago Loop Walking Tour

  1. Start of Route 66 (East Adams and Michigan): The official Historic Route 66 start sign is a great place to start this tour. It’s on a street sign, fittingly, so look up and then turn around and look across the street.
  2. Art Institute of Chicago (111 S. Michigan): Founded in 1879, this Beaux Arts building dates to the 1893 World’s Fair. If you have time a diverse collection of art from ancient to contemporary is found through the doors past the stately lions out front.
  3. Millennium Park (201 E. Randolph): This fabulous part is thoughtfully designed and landscaped featuring the “Bean” (Cloud Gate), the Crown Fountain, the Jay Pritzker Pavilion, the Bridgway, and the Lurie Garden.
  4. Chicago Cultural Center (78 E. Washington): Completed in 1897, this stunning free landmark also known as “The People’s Palace” features the world’s largest stained glass Tiffany dome (30,000 pieces of glass and 38 feet in diameter) in the Preston Bradley Hall, as well as fabulous mosaics around the room and stairs. Across the building is the Grand Army of the Republic Hall and Rotunda with a 40 foot glass dome by Healy and Millet.
  5. Carbide and Carbon Building (230 Michigan): The Carbide and Carbon Company, which developed the first dry cell battery, commissioned the Burnham Brothers (sons of the deceased Daniel Burnham), who completed the structure in 1929. The building’s cap is ornamented with genuine 24 karat gold. 
  6. The Picasso (50 W. Washington): In the 1960s, artist Pablo Picasso designed the three-dimensional, cubist sculpture which stands 50 feet tall and weighs 162 tons.
  7. Chagall’s Four Seasons (10 S. Dearborn): In the 1970s, Marc Chagall composed this mosaic artwork “The Four Seasons” portraying six scenes of Chicago.
  8. Tiffany Dome at Marshall Field (111 N. State): Completed in 1907, there is a 6,000-square-foot mosaic made of over one million pieces of glass designed by Louis Comfort Tiffany.
  9. Federal Reserve Bank Chicago (230 S Lasalle): This Beaux-Arts building dates to 1922 when the Chicago Fed had outgrown its original digs. Go inside to see the cool (and free) Money Museum.
  10. Chicago Board of Trade (141 W Jackson): Built in 1930, the Chicago Board of Trade Building is a 44-story, 604-foot Art Deco skyscraper.
  11. Rookery (209 S Lasalle): First completed in 1888, the Rookery Building is a cornerstone of Chicago’s rich architectural heritage, showcasing the work of some of the city’s great architects, John Root, Daniel Burnham, and Frank Lloyd Wright. The Romanesque Revival building has an amazing staircase inside. 
  12. Willis Sears Tower (233 S. Wacker): Designed by Skidmore, Owings & Merrill in 1974, the former Sears Tower stood as the tallest skyscraper globally until 1996. It is 1730 feet tall and spans 110 stories. Go up in the elevator for 70 second and then hang out in the observatory.

Magnificent Mile Walking Tour

  1. Dusable Bridge (333 Michigan Ave): Introduced in the 1909 Plan of Chicago, this movable bridge draws inspiration from Paris’s Alexander III Bridge and features four decorative corner pylons, sculptural reliefs and abutments. A commemorative plaque marks the site of the Fort Dearborn Massacre of 1812 at the southern end of the bridge.
  2. Aqua Tower (225 N Columbus): Designed by Jeanne Gang, the Aqua Tower holds the distinction of being the tallest building (859 feet) designed by a female lead architect. Balconies which seem to undulate along the exterior give the impression of watery voids.
  3. Wrigley Building (400 N Michigan): This skyscraper across from Tribune Tower boasts two elaborate towers built in the 1920s.
  4. Tribune Tower (435 Michigan): Looking like a Gothic cathedral, the headquarters for the Chicago Tribune was erected in 1925.
  5. Old Chicago Water Tower and Pumping Station (806 Michigan): Built in 1869 by William W Boyington in a Gothic style, the historic Water Tower is a beloved Chicago landmark. It is one of only a few buildings to survive the Great Chicago Fire of 1871.
  6. Fourth Presbyterian Church (126 E Chestnut): Dating to 1914, the sanctuary of this historic church is stunning with beautiful stained glass and an intricate vaulted ceiling.
  7. John Hancock Center (875 N Michigan): Completed in 1970, this skyscraper tickles the sky at 1127 feet. One can experience the thrill of its observatory if you’re not afraid of heights.
  8. Bonus: Navy Pier (600 E Grand Avenue): Part of Daniel Burnham’s plan for Chicago, it opened in 1916. It is filled with games, a spectacular Ferris Wheel (Chicago is known for this invention debuted at the 1893 World’s Fair), food, museums, and more. Take in the water and enjoy the carnival-like spectacle.

Additional architecture to note:

  • Grant Park and Buckingham Fountain (301 S. Columbus): Opened in 1927, Buckingham Fountain was donated by Kate S. Buckingham in honor of her brother Clarence; it is a Chicago Landmark and one of the finest ornamental fountains in America. The fountain is composed of pink Georgia marble, with some granite elements, and bronze sculptures. While in operation, the Fountain produces a major water display for 20 minutes every hour.
  • Museum Campus includes Field Museum, Shedd Aquarium, Adler Planetarium, Soldier Field. Read more: https://www.chicago.gov/city/en/sites/museum-campus-working-group/home/the-museum-campus.html

I hope you enjoyed these walking tours. Please use my links below to get tickets for many Chicago attractions including:

Viator Chicago Attractions: https://www.viator.com/Chicago/d673-ttd?pid=P00161535&mcid=42383&medium=link

Chicago CityPass: https://www.viator.com/tours/Chicago/Chicago-CityPass/d673-2640CHI_TR?pid=P00161535&mcid=42383&medium=link&medium_version=selector

Get Your Guide (small to medium size groups/private):https://www.getyourguide.com/?partner_id=CMSFGKK&utm_medium=online_publisher

Amy French, Ph.D., is the voice behind Roaming Historian. A professional historian and seasoned traveler, she shares stories that blend history and travel to give readers a deeper understanding of the places they explore.

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Photograph of Rookery Stairs, Chicago, Illinois
The Bean, Chicago
Water Tower, Chicago, Illinois
Water Tower
Federal Reserve Bank, Chicago
Home of the Money Museum
Chicago river
Chicago Theatre
Chicago Theatre
Tiffany Dome, Chicago Cultural Center
Tiffany Dome, Chicago Cultural Center

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