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Historical & Heritage Tours in Chicago

THE 10 BEST Chicago Historical & Heritage Tours

Historical & Heritage Tours in Chicago

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Travellers' Choice Awards winners (including the "Best of the Best" title) are among the top 10% of listings on Tripadvisor, according to the reviews and opinions of travellers across the globe.
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142 results sorted by featured
  • Our Featured sort order ranks tours, activities, and experiences by several factors including the revenue generated by Tripadvisor from these bookings, your individual user browsing history and preferences while using Tripadvisor, the frequency of user clicks generally, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.
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Showing results 1-30 of 142
*Likely to sell out: Based on Viator’s booking data and information from the provider from the past 30 days, it seems likely this experience will sell out through Viator, a Tripadvisor company.

What travellers are saying

  • Flyer598228
    1 contribution
    5.0 of 5 bubbles
    We had a great time on this tour! Sophia’s warmth, enthusiasm and knowledge made for a wonderful experience. Would highly recommend this tour
    Written 4 December 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Lone P
    1 contribution
    5.0 of 5 bubbles
    Absolutely amazing tour full of hidden gems, I did not know existed!! Breathtaking, jawdropping beautiful architecture. Ethan was an Excellent guide, so full of historic anecdotes served with a lot of humor. A definite must see tour!
    Written 3 December 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Darren S
    29 contributions
    5.0 of 5 bubbles
    Loved this mob and crime tour
    Guide Jamie Grossman and driver were really friendly and informative
    Fun and full of information
    Saw Chicago about the mob and info I didn’t know about other crimes
    Tour was in unrushed and professional
    I would recommend
    10/10
    Written 2 December 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Lydia
    Naples, FL4 contributions
    5.0 of 5 bubbles
    Dash is awesome! It’s a small tour. Only me and another guy. It was a very cold Monday. Dash knows almost every single building in downtown Chicago. He is friendly, knowledgeable, passionate and thoughtful. The food was great. Dash knows where is the best spot. I would highly recommend people to take this tour. And Dash, definitely is the person you should trust!
    Written 2 December 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Jason C
    Minneapolis, MN2 contributions
    5.0 of 5 bubbles
    Taka was an amazing tour guide! Very knowledgeable and friendly! Everyone had a great time and we would all highly recommend!
    Written 1 December 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • yves G
    1 contribution
    5.0 of 5 bubbles
    Great tour …great guide …we did the cocktail architecture tour
    The experience to see the buildings at nite is just amazing
    Written 1 November 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • craig s
    Bloomington, IN5 contributions
    5.0 of 5 bubbles
    This was a fantastic tour, made that way largely by our wonderful tour guide Kylie. The selection of buildings was wonderful and very intentionally covered a variety of styles. The tour notably included the The Chicago Board of Trade Building, the Marquette Building, the Palmer House Hotel, and the Chicago Cultural Center. Kylie was amazingly knowledgeable about architecture and the history of Chicago. We went on this tour with our 16-year-old niece from Germany, who wants to be an architect. and our niece's best friend (also from Germany). It is a testament to Kylie's tour leading that both young ladies had a great time. I know a little bit about design and at the end of the tour I was surprised at how much I had learned. We booked this tour through TripAdvisor and then at the last minute found out it is actually a Viator-organized tour. I have had tours from Viator that were good in spite of the tour guide. I think this is the first time ever I have been on a Viator-organized tour that was great because of it's tour guide. I cannot say enough about how this two-hour walking tour will enhance your understanding of and love for Chicago.
    Written 1 December 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Dreamer466429
    1 contribution
    5.0 of 5 bubbles
    The Gangster mini bus tour was great! Matthew, our tour guide had amazing stories and was so entertaining! We took the 6 pm ride. So glad we did the bus. Would have been quite cold to walk. He allowed for a few stops off the bus with a great photo spot for the city lights. Was the perfect night activity for teens and adults! Lots of Chicago history included.
    Written 1 December 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Cristy V
    8 contributions
    5.0 of 5 bubbles
    This tour was amazing! Our tour guide, Mike, was phenomenal. We were first-timers riding a Segway, but thanks to our excellent tour guide, we felt extremely comfortable and safe. He was funny and knowledgeable. We had a great time and recommend this tour with Captain Segway 500%!
    Written 29 November 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Daydream09759515365
    10 contributions
    5.0 of 5 bubbles
    I had a fantastic experience with Tours by Foot! Mike made the ghost tour both thrilling and fun, perfectly balancing history with a touch of spookiness!
    Written 21 October 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Traci D
    Smyrna, TN17 contributions
    5.0 of 5 bubbles
    This was a wonderful experience. The tour guide Rick was funny, very informative and accommodating. With a smaller group it was easy to hear and navigate. We were able to see places we didn’t know about and learn some neat facts. We highly recommend!
    Written 4 December 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Laurence P
    Newhaven, UK439 contributions
    5.0 of 5 bubbles
    Wow - what a colelction. The exhibits seemed never ending. Make sure you allow enough time to see everything.
    Food is very expensive here, so take a snack with you if you can (wish we did). $120 for a small lunch / 4.
    Written 26 November 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Joci M
    Stafford, VA1 contribution
    5.0 of 5 bubbles
    The tour was a super fun experience! Our guide was friendly and knowledgeable. The stops were really interesting and full of Chicago’s history. She also told us about other locations to check out if we wanted to find more haunted grounds and ghost stories. Definitely recommend this tour for anyone looking for some haunted Chicago fun!
    Written 31 October 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Venture62796293823
    2 contributions
    5.0 of 5 bubbles
    We had a fantastic time on this tour. Joseph was a great tour guide. He was very knowledgeable and also fun/entertaining ( It was the right mix!) . Keith was an excellent driver. Strongly recommended it to anyone visiting Chicago and hoping to learn more about its rich history!
    Written 27 October 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Roger P
    7 contributions
    5.0 of 5 bubbles
    Our tour guide was Sally and she was wonderful. A wealth of knowledge and so very nice and kind. You get complimentary headphones and a radio that allows you to hear everything about every building. This is an outside only tour so you don’t go up in any building, but was very cool to learn some history and to see the different styles and construction methods. Great tour!
    Written 28 November 2024
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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