The 13 Best Chicago History Tours

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

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

Spend about 4.5 hours walking Chicago’s Loop and River North with a guide such as Dave, Rich, or Dash. Expect architecture, city stories, the Pedway, Riverwalk, Millennium Park, The Bean, and enough samples of deep dish, hot dog, Italian beef, and other Chicago favorites for lunch.

“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.”

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2.Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

★★★★★★★★★★5.0 · 962 reviews · 1 hour 30 minutes (approx.) · from $35Best value

Walk through Chicago’s 6,000-square-foot Medieval Torture Museum at your own pace. Hundreds of torture, restraint, and execution devices are paired with wax figures, audio commentary, hands-on displays, and a ghost-hunting app. The visit lasts about 90 minutes and is best suited to adults and older teens.

“The entire process of ordering tickets, gaining admission and walking through the museum came off without a hitch. The museum has an excellent collection of torture artifacts. Also, many exhibits are hands on.”

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3.Chicago Walking Tour: Historic Treasures of Chicago

★★★★★★★★★★5.0 · 362 reviews · from $35

Walk from the Chicago Architecture Center through the Loop and along Michigan Avenue, seeing the Wrigley Building, Palmer House, Carbide and Carbon Building, Reliance Building, and Chicago Cultural Center. Guides such as Jim, John, Bob, and Maureen bring the buildings’ design and history to life.

“Guide was great. Knowledgable and humorous. Happy for questions and open to question. Truly interesting interiors.”

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4.Chicago Architecture and True Crime Tour

★★★★★★★★★★5.0 · 326 reviews · 1 hour 30 minutes to 1 hour 45 minutes (approx.) · from $35

Walk Chicago’s Loop with guides such as Joseph, David, Kris, and Roan, pairing historic interiors with true crime stories. Visit the Palmer House Hilton, explore downtown buildings, and finish at Chase Tower. Expect about 90 minutes of walking, with time indoors and outdoors.

“My date and I were fans of Jonas - she described him as likable, charming, and sarcastic in a good way. Tour was fun and learned quite a few things”

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5.Historical and Architectural Chicago Fireboat River & Lake Cruise

★★★★★★★★★★5.0 · 246 reviews · 2 hours (approx.) · from $47

Spend about two hours aboard a historic Chicago fireboat, traveling from Lake Michigan through the locks to the Chicago River and back. Guide Cliff is praised for witty, clear talks on architecture and city history. Expect open-air seating, an enclosed warm area, bathrooms, snacks, and drinks for purchase.

“Great tour and guides. Highly recommend. Beautiful to see the city from the water and get to go on the lake and river.”

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6.Walkin’ with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

★★★★★★★★★★5.0 · 218 reviews · 2 hours (approx.) · from $44

Walk downtown Chicago with Colin on a small-group, two-hour tour blending art, architecture, history, comedy, and tragedy. See Chagall’s Four Seasons, Calder’s Flamingo, the Rookery, Picasso’s sculpture, Macy’s Tiffany dome, and the Chicago Cultural Center.

“Colin is very personable and knowledgeable, even though he’s relatively young. He’s interested in art and will show you a bunch of cool things in the city. He’s also very adaptable when we started getting rained on and he just pivoted to underground walkways.”

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7.African American Heritage Tour of Chicago

★★★★★★★★★★4.5 · 127 reviews · 4 hours (approx.)

Join Steve Johnson of Chicago Personal Neighborhood Tours for a four-hour drive through Bronzeville, Hyde Park, and South Shore. See churches, homes tied to major Black figures, neighborhood landmarks, an African American museum, and finish with soul food at Pearls. Pickup options are available.

“This was a long, very detailed, enjoyable tour experience. So expect to spend the full four hours or more. It was worth the time. Our tour guide was full of historical facts and enjoyable. The only disappointment was that the van’s microphone did not work which made it difficult for some to hear. Overall all it was an enriching experience.”

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8.Chicago: Food, History and Architecture Tour

★★★★★★★★★★4.8 · 104 reviews · from $99

Spend 4.5 hours walking Chicago with an English-speaking guide such as Chicago Dave, Daniel, Dash, or Rich. See the Pedway, Chicago Cultural Center, Riverwalk, historic skyscrapers, and Millennium Park while tasting popcorn, a hot dog, deep-dish pizza, and Italian beef.

“One of the best city tours I have done. I have been to Chicago many many times and I learned oodles. Chicago Dave made the tour interactive. They keep it a small group, so no microphones and headsets. Dave was born and raised in the city and his passion for the city comes through in the tour. Great combination of outside and inside and opportunities for sitting and getting drinks. Food was fantastic. At the end of the tour, he recommended what we could do next and gave directions.”

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9.Chicago Walking Tour: Historic Skyscrapers

★★★★★★★★★★5.0 · 67 reviews · from $35

Explore Chicago’s Loop on a 90-minute walk capped at 10 people. A Chicago Architecture Center-certified guide, including guides such as Deborah, Audrey, or Angela Platt, explains the Rookery, Marquette, Monadnock, and other landmark buildings. Your ticket also includes Architecture Center gallery admission.

“amazing city and amazing architecture. Did this tour on sunday, and some buildings were closed.”

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10.Chicago: Historic Gangsters & Twilight Tales Night Cruise

★★★★★★★★★★4.1 · 63 reviews · from $45

Spend 90 minutes cruising the Chicago River at twilight with an English-speaking guide, skyline views, and dark tales of H. H. Holmes, the Eastland disaster, the Chicago Fire, and Chicago mobsters. Drinks are available to buy onboard, but food is not included.

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11.Chicago River Architecture Tour Aboard a Historic Yacht

★★★★★★★★★★5.0 · 45 reviews · from $49

Spend about 90 minutes on Chicago’s river aboard a historic wooden yacht. A captain handles the route while a guide explains roughly 50 buildings, from the Wrigley Building to the Michigan Avenue Bridge. Expect soda, coffee, snacks, and a steady stream of architecture and city history.

“The tour guide was terrific - super informative, fun to listen to, and maintained control of the crowd so that folks could actually hear him. He also invited and answered random questions. The boat ride was smooth and beautiful. I’m so glad we opted for a smaller vessel so we could hear and see everything. This tour was my and my 16-year old son’s (!!) favorite!”

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12.Historic Homes and Cottages of Wicker Park Walking Tour

★★★★★★★★★★5.0 · 44 reviews · 1 hour 30 minutes (approx.) · from $45

Walk through Wicker Park with Ronnie, a passionate architecture guide, and study workers’ cottages, mansions, and old landmarks. The tour covers more than 25 historic properties, with an Atlas app adding photos and background. Expect a small group, a 6:00 pm start, and substantial walking.

“Great tour! Ronnie taught us a lot of history through Wicker Park’s houses and streets, changing the way in which we look at the city forever. Highly recommend!”

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13.Chicago: Historic Architecture Chicago River Small Boat Tour

★★★★★★★★★★4.6 · 26 reviews · 1h 30m · from $67

Join an English-speaking guide aboard a small historic yacht for 90 minutes on the Chicago River. You’ll see more than 50 buildings, from Art Deco and Gothic towers to modern skyscrapers, while learning about their architects, construction, and place in Chicago’s story.

“We enjoyed the smaller feel of this tour vs others that have hundreds of people, but we had a hard time hearing the guide. We were at the front of the boat and between the people around us talking nonstop and the low volume of the speaker, we only heard about half of the tour. This wasn’t the guide’s fault, he was humorous and knowledgeable, but it did affect how much we learned while on the cruise. I also highly recommend arriving very early. Instructions said come 15 mins early and we got there 30 mins early to be safe, and almost every single seat was already taken. Overall, I…”

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