Chicago · CHICAGO HISTORY TOURS
13 reviewed
The Great Fire, the World's Fair, the first skyscraper: Chicago packs a lot into a short century. The best history tours are below, with the eras each one covers, the neighborhoods they walk, the durations, and the prices, so you can pick the story you came for.
Small-group Chicago walking tour with food bites and big architecture stops, plus history stories and a finish near the Loop.
“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.”
Skip-the-line access and optional VIP time at Chicago’s Field Museum, home to Sue, Maximo, and more than 35 world-class exhibits.
“Awesome experience, and very much worth the money and affordable !”
Field Museum admission in Chicago for $29 includes SUE, mummies, gems, and docent tours. Guaranteed entry for a 4-hour visit.
“The dinosaur exhibits were great. The museum had a lot of interesting things that just made you say, WOW!”
A 2-hour small-group Chicago architecture walk linking the Loop’s icons to art deco interiors, with CAC admission included for $35.
“Paul was a great tour guide whose passion for the architecture and history of Chicago’s great buildings was evident. The pace was perfect. I didn’t know the Chicago Architecture Foundation existed, but will definitely sign up for another tour when I return.”
Cruise Chicago on a restored fireboat with expert narration, lake views, river architecture, and fire-service stories. Two hours from $47.
“it was a pleasant trip and the boat cap was very informative and knowledgeable. Enjoyed the history.”
Walkin’ with Colin in downtown Chicago: art, architecture, theatre, and Marshall Field retail history in a fun 2-hour 2-mile walk.
“Amazing experience ! Collin was super friendly and the explanations were great. Would highly recommend ! Thank again !!”
A 90-minute Chicago Architecture Center walking tour of iconic buildings in chronological order, with gallery admission and a small-group guide for $35.
“Very knowledgeable guide. Super personable and answered all questions the group had. Did not feel rushed nor did it feel too long and dragged on”
Skip the stress and explore Chicago’s Field Museum with an all-access pass, docents, and time-flex entry from 9am to 5pm.
“Pick up details - Viator agent overcharged us by $17 for admission. At checkin, retrieval of the vouchers was impossible. The link indicated “bad request”. After 10 minutes and 2 times though the line we finally got our correct passes.”
Tour Chicago’s Black neighborhoods by van, with stops in Bronzeville and Hyde Park plus soul food and museum time—guided by Steve.
“I was shocked at the depth of black history in Chicago and its impact on Chicago’s overall culture. The tour ran longer than expected and we got started late. Overall I’m glad I took the tour.”
Taste Chicago classics and learn Prohibition-era architecture on a small-group walk through the Pedway and Millennium Park Bean.
“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.”
Walk Chicago’s Loop skyscrapers with a certified guide, a small group of 10, and included Chicago Architecture Center gallery access.
“A little disappointing in the boring facts -- and or lack of Modern Chicago far mire interesting ----”
Chicago River night cruise with gangster and horror stories at twilight, plus landmark skyline views. 1.5 hours, $45, drinks for sale.
Skip the crowd with an 8:00am docent-led Field Museum tour, see Sue and Evolving Planet, then explore freely with admission and 3D.
“This was such a great experience! It was just the 2 of us on the tour with our guide Eleanor, who was great. She was very knowledgeable and enthusiastic even at the early hour. It was so great to see Sue and the other dinos up close with no one else around, and we got great pics! Even after the tour (about an hour) we wandered around the rest of the museum and hardly saw anyone for the next hour. Highly recommend if you're an early riser!”
Cruise Chicago’s river on a historic yacht for 90 minutes of architecture, landmarks, and great photo views with included drinks and snacks.
“On one hand, the narrator was extremely knowledgeable about Chicago architecture and history, and occasionally mixed in some humor. And, I could tell that some other passengers were thoroughly enjoying the entire tour and were sorry to see it end, so this is definitely a great tour for some. On the other hand, the narrator never took a breath, talking nonstop the entire time. Literally every single building we passed during the 90-minute tour was discussed, which was quite a feat. Having a narrator on the microphone the entire time also made it impossible to have your own conversations, if that's of interest. If you are extremely passionate about architecture…”
Walk Old Town’s workers cottages with a small group. See fire-era architecture, landmark buildings, and streets tied to Chicago legends.
“Such a fun tour! We live in the neighborhood and wanted to learn a little more about the houses we see each day. Ronnie was so informative, passionate and professional. I would definitely recommend this tour if you are looking to learn about the history of Old Town while viewing beautiful structures along the way!”
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