Cancel

    Open app

    Search

    Route 66 Chicago

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

    Route 66 Chicago Photos

    You might also consider

    Recommended Reviews - Route 66 Chicago

    Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
    Yelp app icon
    Browse more easily on the app
    Review Feed Illustration
    Photo of Andrea U.
    4999
    3457
    27951

    8 months ago

    Helpful 8
    Thanks 2
    Love this 6
    Oh no 0

    6 years ago

    Helpful 22
    Thanks 0
    Love this 28
    Oh no 0

    6 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 0

    9 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    Ask the Community - Route 66 Chicago

    You might also consider

    Verify this business for free

    People searched for Historical Tours 129 times last month within 15 miles of this business.

    Verify this business

    Chicago Architecture Center

    Chicago Architecture Center

    4.8(812 reviews)
    2.7 kmThe Loop

    chicago architecture center boat tour on the "the first lady" was well done. very rainy day but a…read morechoice of remaining upstairs out in the open, where we were given a big umbrella which was nice, or some of our group went downstairs out of the rain. liz our docent was so knowledgable and informing, 11 out of 10 for her.

    If you're in Chiago you have to do the Architecture tour at least once. If you're in Chicago…read moreduring the Summer as I was you can seek sanctuary in the air conditioned lower level. I wish the audio was a little bit louder on that level due to the sound of the fans and people talking. If you like my reviews, consider "following" my profile for reviews all across the SF Bay Area . Why "follow" someone? It causes the person you follow's reviews to tier to top when you pull up a business. I find this very handy when researching venues. Rod's Review grading scale explained. Essentially I personally base it on the likelihood of a return visit and I try to be stingy with 5 star reviews since they should be "special" in my eyes. Price/Value also play a role obviously but there are $ and $$$$ littered across my grading scale. 5 stars - "I'll go out of my way" (approx 6 % of my reviews) 4 stars- "If I was in the area I'd go here and would recommend", (approx 38% of my reviews) 3 stars "Maybe if was nearby", (approx 37% of my reviews) 2 stars -"Would likely not return, Only if you want to go", (approx 16% of my reviews) 1 star -"No thanks, even if I was hungry", (approx. 3 % of my reviews)

    Photos
    Chicago Architecture Center
    Chicago Architecture Center
    Chicago Architecture Center - Amazing right?

    See all

    Amazing right?

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

    Chicago Detours

    4.9(273 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.

    Photos
    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.

    See all

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

    Family Secrets Tour - Frank Jr

    Family Secrets Tour

    5.0(66 reviews)
    2.7 kmNear North Side

    This was probably one of the best tours I've been on, and my fiancé (who has very high standards…read moreabout these things) agrees. We booked a tour for Saturday at 2 pm. There were some technical difficulties and the TV system on the bus ended up not working. Mr. Frank Calabrese Jr was very professional and good-humored about the situation. He offered everyone on the bus the opportunity to come back free of charge so that we may have the full experience with the photos he had been intending to show us. He proceeded to do the tour without the presentation, which honestly was great in itself. He is a very good story-teller, and had a great narrative. He had notes with him but only referenced them a few times to make sure he wasn't forgetting anything. Everything was super authentic and off the cuff. I loved that we went around Chicago and we were able to get glimpses of how the city was like in the 60s-90s. What made this tour so great was that these stories were first-hand. It didn't come from someone who spent hours studying the history; this was his real life. He was very genuine about his experiences, and his anecdote about his kids at the very end of the tour made me tear up a bit. He even invited us to stay for happy hour at the Chop House to have a drink with him to talk. I would highly recommend this tour to anyone, regardless of whether you know the mob history or not. I personally didn't know too much, and still was captivated by his stories. He does have a book (which I definitely intend to read) and a movie in the works!

    I'm a huge fan of true crime and Chicago history, so I'm surprised to say that this was my first…read morecrime tour ever. But everything happens for a reason, and it seems that reason was that I was meant to wait until the perfect one came along -- that, my friends, happened to be the Family Secrets Tour. I met Mr. Calabrese Jr. weeks ago when he presented some of his intriguing life stories at an event at Chicago Chop House, and I knew that evening that I had to book and experience the real deal, aka his bus tours. My friend and I booked a tour for a Friday afternoon recently that started at 2pm, and though there was a bit of a delay because our bus's TV monitors weren't working, Mr. Calabrese Jr. smoothly filled the time with some behind-the-scenes stories he said he usually doesn't share on the tour. I was hooked immediately. To be honest, before this tour, I had no idea the stories his family was involved in were so high-profile (I even talked to my family afterward, and they ALL knew every detail and were mad I didn't invite them! Sorry family!). But even while he showed us news clips, a lot of photos, and told all of his stories, he remained modest, which made the entire experience endearing. Mr. Calabrese Jr. is super charismatic and a great storyteller, and you can tell he genuinely loves telling his story and showing everyone around the neighborhoods where he grew up, and where big moments happened in history to people who were in "the life." I truly enjoyed this tour and I recommend it for anyone who wants an real, honest, non-theatrical recap of Chicago's mob history. The Family Secrets Tour is engaging and delightful. Thank you so much for captivating us, Frank! Can't wait to bring my family along some time!

    Photos
    Family Secrets Tour - Aftermath of the car bomb attached to the underside of Michael Cagnoni's silver 1979 Mercedes-Benz.

    Aftermath of the car bomb attached to the underside of Michael Cagnoni's silver 1979 Mercedes-Benz.

    Family Secrets Tour - Assistant State's Attorney William H. McSwiggin a.k.a. "Hangman Prosecuter"

    Assistant State's Attorney William H. McSwiggin a.k.a. "Hangman Prosecuter"

    Family Secrets Tour - Tina Cruz and Liz Cote with Frank!!

    See all

    Tina Cruz and Liz Cote with Frank!!

    Gray Line Sightseeing Tours - View from our Lincoln Park stop over looking the beautiful Chicago skyline (Scenic North Side Tour)

    Gray Line Sightseeing Tours

    2.3(68 reviews)
    2.3 kmThe Loop

    This company did not provide the services I paid for due to employees who have no idea what they…read moreare doing. if I could give zero I would. Specifically, I ONLY went back to Dubai to go to the Louvre in Abu Dhabi because it was not open on my first trip. I selected the tour that provided this and it was all set up for Sunday. Without asking me someone changed my tour ( I did not consent to this change) to Monday'; the museum is not open on Mondays. i was told this was a mistake but since I only went to see this museum this was a MONUMENTAL MISTAKE. I took off work, paid for their services and flew to Dubai for a specific reason. I did not get to see the museum, not because it was a holiday or it was under maintence but because some employee had no idea what they were doing. When I complained and asked for a partial refund since I did not get what I paid for, I was offered a free trip to Abu Dhabi when I come back to Dubai. This is unacceptable since i have no intention of returning to Dubai any time soon or know if I ever will. This is a very large company and while mistakes happen, the cost for me should not be so high. They screwed up a trip I carefully set up for my purpose due to incompetence and then refuse to accept responsibility. Be very careful in choosing this company for dream vacations because they could get messed up and then they will do nothing about it

    Candace is the best driver and tour guide. She made our ride entertaining and fun. She puts her…read morewhole heart in her job. She new passenger by name. We had trivia questions and prizes.

    Photos
    Gray Line Sightseeing Tours - Abraham Lincoln Statue

    Abraham Lincoln Statue

    Gray Line Sightseeing Tours - Buckingham Fountain

    Buckingham Fountain

    Gray Line Sightseeing Tours - Chinatown

    See all

    Chinatown

    Shoreline Sightseeing - Top deck - guide Joe

    Shoreline Sightseeing

    4.7(1.9k reviews)
    3.8 kmNear North Side

    Loved it! This boat tour was my favorite part of our trip!! The boat had plenty of room. Some…read moreseating was protected from the sun with an overhang and a bar. It also had an open area with bench seats that had a good amount of lean, so that you can see the highest points. The guide was awesome. I learned a lot about Chicago's history and architecture trends over the years. A lot of the buildings "front" side faces the river, so the view is very different from the boat. The boat ride was smooth with great views. I highly recommend!!!

    Just did the 60-minute architectural river tour departing from Navy Pier this past weekend and it…read morewas a fantastic experience. Our guide Ruby was awesome - engaging and funny with a perfect mix of architectural history and fun facts that kept everyone entertained. Right before docking at the end of the tour, the captain turned the boat toward the river entrance for a minute so everyone could take photos in front of the skyline, which was a nice touch. The biggest selling point for me was that all of Shoreline's tours are dog-friendly. I brought my pup Shadow along and they even gave her a treat as we were boarding. A couple tips: getting your tickets on Groupon will save you a couple bucks off retail, and bring your own water if it's a hot day - beverages on the boat are pricey. Great guide, amazing views, and pet-friendly. Highly recommend!

    Photos
    Shoreline Sightseeing - Merchandise mart

    Merchandise mart

    Shoreline Sightseeing - View of (former) Sears Tower  See the Chicago's architectural landmarks on this relaxing river tour

    View of (former) Sears Tower See the Chicago's architectural landmarks on this relaxing river tour

    Shoreline Sightseeing - 07.03.25 Navy Pier [Lake Michigan Skyline Cruise in Chicago]

    See all

    07.03.25 Navy Pier [Lake Michigan Skyline Cruise in Chicago]

    Medieval Torture Museum  - Flagel Pillory

    Medieval Torture Museum

    4.4(203 reviews)
    2.3 kmThe Loop

    Very amazing tour! Shows the punishments of the medieval times and the pain and suffering inflictedread more

    Who knew there were so many ways to be tortured throughout history? That was my takeaway from…read morevisiting the Medieval Torture Museum in the heart of the Loop. Looking on their website, there are other torture museum outposts in Florida, California, Branson (MO), and Berlin, Germany in addition to Chicago. The Chicago location is on the compact side, but packs over 100 medieval artifacts into dimly-lighted, macabre space occupying two levels. My timing for visiting was right around Halloween. I purchased tickets online (can get a very slight discount buying online) for a friend's belated birthday. He had always wanted to see this space, and we had scheduled an outing here, followed by happy hour libations. My interactions with the front-desk/check-in personnel (a younger gentleman and a woman getting off of her shift) were pleasant and professional. The young man mentioned that he was studying art. I'm sure this museum gave him plenty of inspiration. To the side of the check-in/welcome area there is a souvenir shop. I didn't really see anything that grabbed me, but there were a couple of promotions taking place and the displays/signage were memorable and lighthearted, considering the grim subject matter. Before making our way to the exhibit, we cued up the audio guide on our phones. The guide is easily accessible through Apple and Android, although I wish I had brought headphones, as I quailed at blasting the sound through speakers with other patrons around. Fortunately, this is more of a selfie and photography-geared space, so there were no dirty looks as I would have expected in a traditional museum or gallery. This museum has something for everyone, whether one is an avid reader of all of the informational material around the exhibits (raises hand) or prefers a more interactive, hands-on experience and photo-ops to capture the thrills and chills. Among the most arresting items are a torture rack from 15th-century Spain and a life-size replica of Joan of Arc being burned at the stake. Over the sound system, occasionally dramatized screams and creaking chains play to heighten the creepy ambiance. All told, it took around an hour to peruse the space, sharing impressions and taking photos.

    Photos
    Medieval Torture Museum  - Medieval Torture Museum

    Medieval Torture Museum

    Medieval Torture Museum  - Torture

    Torture

    Medieval Torture Museum  - We all have that 1 coworker

    See all

    We all have that 1 coworker

    Route 66 Chicago - historicaltours - Updated May 2026

    Loading...
    Loading...
    Loading...