The 11 Best Walking Tours in Chicago

1.Chicago in a Day: Food, History & Architecture Walking Tour

★★★★★★★★★★5.0 · 1,153 reviews · 4 hours 30 minutes (approx.) · from $100Our pick

Start beneath the Chicago Theatre marquee and walk with a local guide through the Loop, the Pedway, Riverwalk, Magnificent Mile, and Millennium Park. You’ll sample Chicago staples including deep-dish pizza, a hot dog, Italian beef, and popcorn. Guides such as Dave, Dash, and Rich are praised for personal stories and thoughtful help.

“This was a nice walking tour with some tastes of Chicago. The tasting part started a little over halfway into the tour (though we did start with some popcorn at only an hour in) so be sure to eat a good breakfast if you choose the 10am tour. By the end id had plenty of food so it’s definitely equivalent to a meal. Pacing was a little slow, I felt like we did a lot of standing around at times, but we did have a smaller group so I assume the tour is paced for larger groups. Overall we had a great time and Chicago Dave was a great tour…”

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2.Chicago’s Secret Interiors Architectural Walking Tour

★★★★★★★★★★5.0 · 635 reviews · from $35Best value

Walk from Union Station through Chicago’s Loop to the Marshall Field Building, entering grand spaces most people pass without noticing. Your guide may be Ethan, Grant, Ty, Matthew, or another city specialist. Expect about two hours, frequent stops, and interiors such as the Rookery, Palmer House, Marquette Building, and Macy’s Tiffany dome.

“Very interesting and surprisingly beautiful. Knowledgeable tour guide and good way to get some exercise / see the city”

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3.Secret Interiors Architecture Walking Tour

★★★★★★★★★★4.9 · 498 reviews · 2 hours · from $35

Meet Grant, Talia, Annie, Angel, or another English-speaking guide inside Union Station for a two-hour walk through Chicago’s Loop. Visit grand interiors at the Rookery, Field Building, Marquette Building, Palmer House, Cultural Center, and former Marshall Field store while learning how architects solved lighting and structural problems.

“Talia was an excellent guide and this tour was a perfect afternoon activity for our family. We discovered architectural gems we’d never seen, even after living in the city. Talia blended the right amount of history, fun factoids and interesting stories. We highly recommend!!!”

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4.Chicago Walking Tour: Art Deco Skyscrapers Loop

★★★★★★★★★★5.0 · 138 reviews · from $35

Walk through Chicago’s Loop with a Chicago Architecture Center certified guide, spotting Art Deco details at 30 N LaSalle, the Rookery, 135 S LaSalle, 1 N LaSalle, and the Board of Trade. Expect a small group of up to 10 people, selected interior visits, and gallery admission at the Chicago Architecture Center.

“This tour is a must on a visit to Chicago... so much of the city's earlier 20th century history is captured in this tour of the moderne art deco architecture. One does not tend to appreciate these gems hidden among the neo-classic buildings and glass high rises, but once seen, a lasting impression that will keep us looking in the future. Leaves one with the question if in 80 years people will be making glass and steel tours. Somehow, one doesn't get the feeling of enduring beauty as one does with Art Deco.... The detail work on the interiors of these amazing buildings is beautiful, and quite lacking in anything…”

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5.Chicago Architecture Walking Tour: Incredible Art Deco Interiors

★★★★★★★★★★5.0 · 85 reviews · 2 hours (approx.) · from $35

Spend about two hours exploring Chicago’s Art Deco buildings, with several interior stops most city tours skip. Guides such as Henry and Hilary explain the style, history, and details in an engaging way. The group is capped at 15, begins near a metal horse sculpture at 425 S Financial Pl, and ends near Pendry Chicago on Michigan Avenue.

“Wear comfortable clothes and shoes. Guide was interesting and fun to listen to. Educational even for an Architect.”

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6.Chicago Architecture Walking Tour: What’s New

★★★★★★★★★★5.0 · 64 reviews · from $35

Walk Chicago’s riverfront and Michigan Avenue with a Chicago Architecture Center guide such as Paul, Paula, Mary Jo, or Mary Ann. In 90 minutes, you’ll examine recent buildings, Tribune Tower’s updates, small apartment design, 465 N Park Drive, the St. Regis, and Apple’s striking store, plus visit the CAC galleries.

“We loved our rainy tour with Paul! He was able to answer all our questions and had a grat outlook on a less than ideal Chicago day. Highly recommend!”

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7.Chicago Walking Tour: Art Deco Skyscrapers Riverfront

★★★★★★★★★★5.0 · 53 reviews · from $35

Walk from the Chicago Architecture Center to THE MART, stopping at five Art Deco landmarks along the riverfront and in the Loop. You may enter grand lobbies at the Carbide and Carbon Building, former Chicago Motor Club, Trustees System Service Building, and Merchandise Mart, though access can change. Guides such as Mitch, Ron Roman, and Marcia add history and sharp detail.

“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”

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8.Chicago in a Day: Food and Architecture Private Walking Tour

★★★★★★★★★★5.0 · 53 reviews · from $272

Spend about five hours with a Chicago guide exploring the Loop, Pedway, Riverwalk, Wrigley Building, Tribune Tower, and Water Tower before tasting classic foods such as deep-dish pizza and a Chicago hot dog. Morning and afternoon departures are available, with groups limited to 12.

“I thought this tour was fantastic. Our guide Dash was hands down the best tour guide I've ever had. He filled the 3 hour architecture part of tour with a bunch of wonderful spots and was extremely knowledgeable of every aspect of all of them. I felt like he could have easily dRead more”

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9.Chicago Walking Tour: Modern Architecture

★★★★★★★★★★5.0 · 50 reviews · from $35

Walk from the Chicago Architecture Center through the Loop with a certified guide, studying Mies van der Rohe, Bertrand Goldberg, Cor-Ten steel, Marina City, and the Chicago Picasso. The 90-minute tour includes CAC gallery admission, a maximum of 15 people, and plenty of architectural stories along the way.

“Loved the tour. Kathleen was great and walks fast!! We learned slot about the wonderful Chicago mid century modern buildings!”

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10.Chicago Art Deco Madness Walking Tour

★★★★★★★★★★5.0 · 31 reviews · from $45

Walk through Chicago’s Loop with Ronnie Frey, an interior designer and architecture guide who points out about seven Art Deco buildings, striking interiors, public sculpture, and Roaring Twenties stories. The 1-hour-45-minute tour is limited to 10 people and includes the Board of Trade, Macy’s, and the Carbide and Carbon Building.

“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!”

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11.Art Deco Skyscrapers Walking Tour

★★★★★★★★★★4.8 · 28 reviews · 1h 30m

Meet your Chicago Architecture Center docent at 30 N LaSalle Street for a small-group walk through five Art Deco skyscrapers near the Chicago River. See geometric interiors, learn about 1920s design, and finish at the Merchandise Mart. Your ticket also includes admission to the Center’s exhibits.

“A lovely man, funny and knowledgeable about his subject!”

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