Chicago · HISTORICAL TOURS
The fire, the World's Fair, the stockyards and the machine politics that followed. These 15 put the story on the ground it happened on, priced and timed, with a note on how much walking each involves.
Taste deep-dish pizza, hot dogs, Italian beef, and Chicago architecture on a small-group walking tour of the Loop and River North.
“David was an awesome guide of the city. Chicago is an amazing town and we learned so much. The food and architecture is top-notch. We had a great time and our group was fun!”
Review the Field Museum in Chicago, with Sue, Maximo, ancient cultures, ticket options, VIP access, crowds, and practical planning tips.
“Our early morning tour with Callisto was worth every penny! We enjoyed the most popular exhibits of the museum all by ourselves and our guide happily answered all of our questions. Highly recommended!”
See SUE, Egyptian mummies, dinosaurs, jade, and 13,000 years of human history at Chicago’s Field Museum with flexible admission.
“It was a beautiful experience. The museum is chock full of collection of different topics. You have to soak up them.”
Explore Chicago’s landmark buildings on a two-hour small-group walk with expert guides, grand interiors, and Chicago Architecture Center admission.
“All tours were great--Dash, Grant and the 3rd tour I took. The Architectural River tour w/ Wade was fantastic”
Cruise Chicago’s river and Lake Michigan aboard a historic fireboat, with architecture, city stories, lake views, snacks, and a full bar.
“Amazing tour in a restored active duty Chicago fireboat. Guide had an amazing amount of Chicago knowledge. Much fun!”
Explore Chicago’s art, architecture, department-store history, and local stories on Colin’s funny, compact two-hour walking tour.
“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.”
Explore Chicago’s Field Museum with SUE the T. rex, mummies, dinosaurs, gems, and special exhibits on an all-access day pass.
“I opted for a guide but was not assigned to one so I definitely recommend asking for one first thing because there is a lot of information to take in. But still easy to navigate through without one & just using the map.”
Explore Bronzeville, Hyde Park, and South Shore with Steve Johnson, learning Chicago Black history, music, politics, and culture by air-conditioned van.
“The tour was very educational and fun. Mr Johnson knew all of the in and outs of Chicago. I would recommend this tour to family and friends.”
Taste hot dogs, deep-dish pizza, and Italian beef while exploring Chicago’s architecture, Pedway, Riverwalk, and Prohibition past.
“Wallach was a terrific tour guide. The tour was really fun and interesting. We saw and learned so much about Chicago!”
Explore Chicago’s early skyscrapers on a 90-minute small-group tour with a certified guide, CAC gallery admission, and landmark architecture.
“My wife and I learned a lot! Deborah was very passionate about the living history of the skyscraper. One-of-a-kind tour!”
Cruise Chicago’s river at twilight while hearing eerie tales of mobsters, disasters, H. H. Holmes, and the city’s glowing skyline.
Enter Chicago’s Field Museum before opening, tour SUE and Evolving Planet with a docent, then explore the galleries at your own pace.
“Wonderful experience! Turned out we were the only two people on the tour which made it extra special. Highly recommend this one! Worth every cent.”
Cruise Chicago’s river aboard a historic wooden yacht, with expert architecture commentary, skyline views, snacks, and a small-group feel.
“The historic information provided was interesting and informative. I recommend this tour for anyone visiting Chicago highly!”
Explore Wicker Park’s workers’ cottages, mansions, and landmarks on a small-group Chicago architecture walk with local guide Ronnie.
“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!”
Cruise Chicago’s river past 50-plus architectural landmarks on a 90-minute small-boat tour with expert commentary, coffee, and snacks.
“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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