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    Chicago Detours

    4.9 (272 reviews)
    Closed 9:00 am - 6:00 pm

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    Reviews With Photos - Chicago Detours

    Noel L.

    I've never been on a guided tour but it was a rare warm spring day in Chicagoland so I decided to throw the Little One in the car and spend the day in the city. I've never been on an organized tour anywhere but spur of the Took the Loop Architecture tour with Chicago Detours and was pleasantly surprised. Two hours and a mile around downtown, learned some little known facts about Chicago and really liked how our tour guide kept encouraging us to look at our surroundings in a different way. Babygirl hung in there pretty good but I wouldn't recommend it for younger kids as architecture might not keep their attention She was squirrelly about an hour in but our group helped entertain her lol (Also not the greatest for strollers with the stairs but it was manageable with an umbrella stroller) But at the end the tour guide asked her what her favorite part was and she said "looking at the ceilings", so guess she was paying attention to some of it! (Saw some amazingly beautiful Tiffany mosaics) We hit the Marquette building, civic center plaza, Chicago Temple, old Marshall Field's, Chicago Pedway (an underground walkway that connects over 5 miles of businesses - I had no idea this existed!!), and ended at the Chicago Cultural Center. It was cool to slow down and observe these buildings as art, rather than take them for granted as I'm rushing by. Can't wait to go on another!

    Michelle R.

    As a food tour enthusiast, I was not sure how a virtual tour could compare. From the host, to the amazing stories behind the city, I cannot wait to spend some time in Chicago exploring. I am super excited to participate in their other tours as well as the tour left me wanting to learn more. Price for admission is definitely worth the amount of knowledge shared. Kudos to your team for putting together a great presentation.

    Billy Goat Tavern, this sign relates to a Saturday Night Live skit about the place.
    Brad N.

    Took the Historic Bar tour last weekend. Wasn't really sure what to expect, but was definitely pleased afterward. Not much walking as the bars/restaurants that are visited are very close to the meet-up point. Tour guide was very informative and educated on the material. The iPad that was carried along and used as an aid to the tour was a very nice touch. Appetizers and drinks were good. Maybe only thing I would change would be to have a themed drink or something relevant to each location. The beer and wine option were fine, but a cocktail option would have been welcomed.

    Angela S.

    I am fascinated by Chicago history, and if you're looking for a fun company outing, I highly recommend taking a Detour with Elizabeth! I recently went with my co-workers on the 1893 World's Fair Tour and absolutely LOVED my experience. My grandmother was at the 1933 World's Fair, so I couldn't wait to learn more about the history of 1893. With a perfectly-sized group of 12, we started out at the Congress Hotel and worked our way around the area. Elizabeth had two iPads, one for each group to view photos and maps to accompany the tour. Without going into too much detail, I loved learning about underground passageways and seeing an alleyway stop I had no idea even existed! If you're an architecture buff you'll love this tour, because the stories all relate to the Fair. One of my favorite stops was at the Berghoff, where we got to sample some favorites off the menu. Fun and games along the way made it possible for us to connect with the tour...but I won't tell you how. Elizabeth is knowledgeable and easy to engage. Detour also has other tours, and I hear the south side one is a blast!

    Wesley W.

    I took the Inside the Loop Interior Architectural Walking Tour with Elizabeth on a Friday afternoon. I wasn't quite sure what to expect but it turned out great as the tour lead us through a handful of historic buildings which are more off the beaten path. Highlights include the Macy's building (originally Marshall Fields), Chicago Cultural Centre, the sky church at the Chicago Temple Building, Block 37, stories on the public transportation system and much more. A sample of a local frozen kefir cafe (like frozen yogurt) was also set up which was a nice touch. I was surprised to hear that most people on this tour are from the Chicago area. It says a lot about the quality of Chicago Detours that locals are even signing up to take this tour of their own city. If available, I would recommend using a two for one on any of the deal sites. $26 is steep for a walking tour but for two people, it's for sure worth it.

    Rachel D.

    I went for the historic pub tour and it was not at all what I was expecting.... It was much more architectural than I expected and I was pleasantly surprised!! Our tour guide was outstanding, very funny, knowledgeable & really focused on getting everyone of our 5 person group to participate in the tour by asking us to point out what we noticed about specific buildings and getting us to guess what the building were used for when they were 1st built. We had appetizers at three of the places we visited that were included in the cost of the tour, they were ok but nothing I would have ordered. I chose to give the additional $18 for 2.5 servings of beer at the same three places where we got the food. The beer was basic and nothing too great... If there was one thing I would suggest for the tour company it would be to allow the person to chose either light beer or dark beer, just like there was an option for red wine or white wine. But other than that I was a really good tour!! I would for sure suggest Detours for anyone in Chicago and I hope this company adds other cities!

    An architect for a tour guide!
    Mike D.

    Pedway cruising and a trip to the odd and perhaps a little bit modern creepy block 37 made this tour fun! (Inside Architecture). Great for a stroll through the parts unknown. We got a great map of the pedestrian system (If you can even follow that) and a surprise for Pastoral!). Loved it!

    Ami P.

    I've been to Chicago several times, but the historic walking tour gave it a different perspective. We participated in the evening tour which started off at the Chicago Tribune tower. Our tour guide was so knowledgable and engaging! For the price of the tour that includes appetizers and drinks, it was so worth it. We stopped by at least 5 places, including the infamous speakeasy that Al Capone was a regular at. I highly recommend this tour if you're looking to get more history information about Chicago!

    the trip is as good as you can imagine. the guide told so much history and interesting stories about an old polonian community that I learned a lot while enjoyed the time. This is my very first chicago detour experience and is sure not going to be the last one!

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    12 years ago

    Interesting and interactive! Went on the interior architecture tour and learned a lot I didn't know about the city.

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    14 years ago

    Loved the Historic Bars tour! I can't wait to go on another tour, and I've lived in Chicago for 22 years! Will definitely recommend!

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    Page 6 of 7

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    Chicago Architecture Center

    Chicago Architecture Center

    4.8(816 reviews)
    1.5 miThe Loop

    This is a must-do when you visit Chicago. The architectural tour was very fascinating and…read moreinformative. While the tour is an architectural focus, Chicago's history is intertwined, and it was interesting to see how historical events influenced design and the planning of the area. Our tour guide, Jessica, was so knowledgeable and a great speaker. The tour lasted almost 90 minutes, and traverses the three branches of the Chicago River. The boat offers seating on the top deck and inside. For the best views, the top deck is better. We took the 10:00 tour, and there was ample seating in early June.

    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)

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

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    Amazing right?

    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)
    1.8 miThe 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

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    Chinatown

    Family Secrets Tour - Frank Jr

    Family Secrets Tour

    5.0(66 reviews)
    1.1 miNear 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!

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    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!!

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    Tina Cruz and Liz Cote with Frank!!

    Chicago Detours - foodtours - Updated July 2026

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