CHICAGO · ILLINOIS
The best of Chicago.
The 15 best architecture walking tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.
A 2-hour Loop walking tour focused on jaw-dropping building interiors, ending at Chicago Cultural Center, with a local guide for $35.
Most Popular“Very fun tour guides, he was well educated about the city and knew a lot of minute details that you would miss out because you dont know what to look for. Excellent tour!”
Deep-dish, hot dog, Italian beef and Chicago skyline stories on a small-group 4.5-hour walk with the Pedway and The Bean.
“Dave was very knowledgeable & friendly. Freezing outside but still was able to provide a great experience both inside & outside! I would do this tour again.”
Chicago Loop interiors and skyline views on a 2-hour walking tour with rare access to lobbies, domes, mosaics, and iconic landmarks.
“Ethan our guide did an incredible job. Chicago is such a beautiful city with such a rich architectural history. Was a great way to see things you had no idea were even there.”
Chicago Loop secret interiors tour: $35, 2 hours from Union Station to iconic landmarks. Learn how light and structure shaped the city.
“Our guide Grant was fantastic! My friend and I took the tour on a cold February day and enjoyed every minute of it. Grant is very personable and knowledgeable. The architectural details we saw were stunning. Definitely recommend this tour!”
Walk Chicago’s Loop underground on a small-group architecture tour through the Pedway, art stops, and key buildings for $35.
“Kaylee is the best tour guide! She says she's a nerd for this stuff but I say she's an expert with a love of all that is Chicago and its hidden gems! Came to Chicago during historic freezing temperatures, -24, and wanted to find something to do without freezing and this was PERFECT! Highly recommend…”
Explore Chicago’s Underground *Pedway* with an expert guide, secret interiors, and art meaning clues near Millennium Park.
“The guide was very knowledgeable about the history of Chicago , the buildings and the pedway.”
A small-group Loop walk focused on Chicago’s art deco skyscrapers, with interior stops and Chicago Architecture Center gallery admission.
“This your was excellent. Our your guide Bill was so knowledgeable and made the your so enjoyable. Could not recommend this your highly enough.”
Step inside Chicago’s Art Deco landmark interiors on a small-group 2-hour architecture walk, with photo time and a pro guide.
“Lack of red horse, so could not find start of tour. Scammed out of a lot of money. Bummer. Would not book with this company again.”
A small-group Chicago Architecture Center walk focused on new Loop buildings, CAC galleries included, plus quick stops at Tribune, St. Regis, and Apple.
“We had a wonderful tour experience led by Paul S. of “What’s New” in Chicago architecture. I appreciated the breadth & depth of information shared and the “stories” presented about the architects, buildings, and community spaces viewed.”
Chicago Art Deco riverfront walking tour with CAC lobbies, five big Art Deco stops, certified guide narration, and small-group pace for $35.
“This is a wonderful walking tour. We visited a lot of landmarks like the Mart and the carbon and carbide building. Our guide, Ron Roman, was approachable, professional, and above all knowledgeable. We learn so much from the tour. ArchitRead more”
A 2-hour guided walk through Chicago interiors: Art Deco elegance, Frank Lloyd Wright renovations, Moorish vaults, and the Tiffany dome.
“Henry was a fantastic guide with lots of interesting infos and a lot of passion.”
Chicago Loop art deco walking tour with interior-designer guide, small group, about seven 1920s buildings, plus lobby views when open.
“It was terrific! The art deco is so beautiful and cool, but the histories behind the buildings and architecture made it even better. Excellent experience!”
Chicago Art Deco walking tour: enter five riverfront lobbies, learn the style’s Paris roots and motifs, led by Chicago Architecture Center.
“It was very informative”
A small-group guided walk through Chicago’s Pedway, plus holiday sights, a ride on the L train, and an end at The Bean.
“When I first heard about an underground walkway, I knew I needed to see it with an experienced guide. This tour was SO fascinating. Going in and out of unnoticeable parts of buildings down to the pedway was a treat. Our guide was knowledgeable and showed us many art & architectural treats. One of our…”
Chicago architecture walking tour ends with a narrated river cruise past 40+ landmarks, plus The Bean, Pedway, and Navy Pier.
“Very informative, lots of walking, Andrew is very knowledgeable and polite, will ask you if you need to stop and rest anytime you want”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
