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    Route 66 Chicago

    4.5 (4 reviews)
    Closed 9:00 am - 7:00 pm

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    11 months ago

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    6 years ago

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    People searched for Historical Tours 186 times last month within 15 miles of this business.

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    Chicago Detours - Beyond dates and names of architects, we dig into the ways in which we interact with architecture.

    Chicago Detours

    4.9(272 reviews)
    2.6 kmRiver West, Noble Square, West Town

    During Parents' Weekend at the University of Chicago, the university offered tours of the…read moreneighborhood through Chicago Detours. My wife did this tour a couple years ago and highly recommended it, but I wasn't especially interested because I had also gone to school here and figured I knew enough about Hyde Park already. However, she insisted that it would be worth our while and so I agreed to climb on the bus. And it was the absolutely right decision, because the tour was excellent. In fact, it wasn't just a tour of Hyde Park. It included the surrounding neighborhoods of Washington Park, Kenwood, Jackson Park, and Woodlawn. Since this was a UChicago sponsored event much of the information related to the University's investment and involvement in the area. Our tour guide and founder of Chicago Detours, Amanda, is herself a graduate of UChicago and thus she had some additional insight into the relationship with the community. Though the 75-minute tour felt a little slow-going at times, there was much to learn about the vibrant but sometimes troubled history of the area. Amanda has tremendous knowledge and the excursion was both fascinating and entertaining. I can imagine that Chicago Detours would have equally interesting tours of other neighborhoods in this diverse city.

    Virtual tours are such a cool thing to do right now. I attended a Yelp Elite event that was a…read morevirtual food tour of Chicago. It was incredibly informative and a good balance of history and current trends. Looking forward to attending more virtual tours, like the World's Fair and the Cruise From Your Couch Boat Tour. I loved seeing the pictures of the in-person tours and can't wait to attend some of those too.

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    Chicago Detours - On an architecture tour, you'll venture into spaces many locals don't know

    On an architecture tour, you'll venture into spaces many locals don't know

    Chicago Detours - Enjoy drinks in opulent settings like the Chicago Athletic Association Hotel on the 1893 World's Fair Walking Tour with Bars and Food.

    Enjoy drinks in opulent settings like the Chicago Athletic Association Hotel on the 1893 World's Fair Walking Tour with Bars and Food.

    Chicago Detours - Historic Walking Tour with Bars- drink, learn, eat, explore.

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    Historic Walking Tour with Bars- drink, learn, eat, explore.

    Chicago Food & City Tours - Urban Belly caramelized chicken dumplings

    Chicago Food & City Tours

    4.8(691 reviews)
    3.5 kmRiver East, Near North Side

    My 13 year old daughter and I enjoyed the Iconic Foods of Chicago tour yesterday. Our guide Lillian…read morewas fantastic! the food was all amazing and I especially enjoyed all of the history she shared about the foods and neighborhoods of Chicago. Highly recommend!

    Amazing amazing amazing! My best friend and I absolutely loved the "Yes Chef! Chicago: A Bear…read moreInspired Food Tour". Casey, our guide, was phenomenal. So fun and witty, and he really went above and beyond to make sure we had a great experience. All the places we visited were very special and iconic, including a bakery that's 115 years old and an ice cream shop that's 105 years old. It was really fun remembering where these places appeared in the show. Another perk of the tour was skipping lines and having special areas and service just for us. And not having to drive and look for parking. The air conditioned bus was lovely and comfortable, and it was fabulous to be driven around different neighborhoods. We went to so many great places and it's a fun way to get to know the city better. We ate so much good food!!! Italian beef sandwich, charcuterie, pepperoni pizza, hot fudge sundae, strawberry donut and more. Great drinks too! Beer and cocktails, or soda. I didn't need to eat for the rest of the day! Everything was delicious! I highly recommend this tour! It was exceptional and worth every penny.

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    Chicago Food & City Tours - Mr. Beef beef sandwich with hot peppers

    Mr. Beef beef sandwich with hot peppers

    Chicago Food & City Tours - Pizza Lobo pepperoni pizza

    Pizza Lobo pepperoni pizza

    Chicago Food & City Tours - Our tour guide in a local temple.

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    Our tour guide in a local temple.

    Chicago River Boat Architecture Tours - Our boat

    Chicago River Boat Architecture Tours

    4.7(292 reviews)
    3.4 kmNear North Side

    Such a great city for architecture, the very oldest building sitting next to the newest…read moreskyscrapers. I loved this tour...even though it rained and we had to spend part of the tour inside to stay dry without much of a view, it was still a great tour for the cost. We were warned to make a reservation cause the tours do fill up, and this was a holiday weekend. Do not leave Chicago without doing this!

    There are many different boat tours out there with different prices and different lengths of time I…read morewould definitely recommend the architect boat river tour. I would say if you have 90 minutes this boat tour is a must do. I believe the option times that we had to choose from was anywhere from 10:00 a.m. for the first boat going out and the last boat was 4:00 p.m. but check the website for exact times. We booked our tour online to make sure that we got the time and date that we wanted to we preferred earlier in the day. We booked about 2 months out. These tours fill up quickly especially in the summer time. We started lining up about an hour before to make sure we got a seat up top so we could enjoy the view. If you prefer to sit inside you still will be able to hear the tour guy just you may not be able to see everything he is announcing it may be on the other side of the boat which you may not see if you're inside because of other people that are sitting. Our tour guide was wonderful explaining the different buildings and if you had any questions he would definitely answer those questions later on. This was my second time in Chicago I learned many new things by going on the tour I am glad that I did and I would recommend anyone else to do so as well.

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    Chicago River Boat Architecture Tours - Boat top floor

    Boat top floor

    Chicago River Boat Architecture Tours
    Chicago River Boat Architecture Tours

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    Route 66 Chicago - historicaltours - Updated August 2026

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