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    Gray Line Sightseeing Tours

    2.3 (68 reviews)
    Closed 9:00 am - 5:00 pm

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    Great tour of the north side. Mitch was great and super funny! Unbelievable how he drives that bus on those city streets.

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    Review Highlights - Gray Line Sightseeing Tours

    The Gray Line Trolley worked out pretty well for us as a mode of transportation around the city of Chicago on a Sunday.

    Mentioned in 2 reviews

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    Family Secrets Tour - Frank Jr

    Family Secrets Tour

    5.0(66 reviews)
    0.9 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!

    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!!

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    Tina Cruz and Liz Cote with Frank!!

    The Barrel Run

    The Barrel Run

    4.9(129 reviews)
    0.9 miRiver North, Near North Side
    $$

    If you're a craft beer fan this tour should be on your list of things to do if you're visiting…read moreChicago. You get to visit 3 breweries/brew pubs. I believe at least one of them you get a tour of, Revolution brewery was the one we got to tour. Our guide Ted was awesome, he gave us some history on the places we were going to visit along with some local Chicago history during the ride. The location were kept a surprise ahead of time so we didn't know where we were going until we got there. They do have a rotation of different breweries they tour so if you decided to go again you could possibly explore some new spots the next time around. The coolest part about the tour is the bus itself, just checkout the pictures. The seating layout makes for great interaction with the rest of the people on the tour. I happened to find out about The Barrel Run when I was looking up Chicago tours on YouTube & came across some video a couple named kovACTION made about 3 months ago. Right after watching that I knew I had to fit this in my schedule when I was in town.

    The Barrel Run provided an exceptional experience. For my sister's 40th birthday, we arranged a…read moreprivate Prohibition Tour, which proved to be truly remarkable. Our tour guide, David, was an outstanding narrator whose extensive knowledge offered many new insights, even for those in our large group who reside in the Chicago area. Furthermore, Denise, who served as the primary point of contact for scheduling, was excellent; her communication was consistently thorough. I highly recommend The Barrel Run for anyone seeking a unique and memorable event.

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    The Barrel Run
    The Barrel Run
    The Barrel Run

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    Tea Around Town - Tea Around Town Chicago Experience

    Tea Around Town

    1.7(105 reviews)
    0.3 miThe Loop

    VIP High Tea Tour of Chicago? Nay. Temu High Tea Tour of 2 blocks of Chicago…read more If the experience wasn't absolute comedy, I would be more upset. I booked this high tea as a birthday gift for my best friend. I'm an idiot and didn't read any reviews. I was trying to decide between 3 high tea experiences in Chicago, and our husbands agreed this one seemed the most fun. Well, it was more entertaining than any high tea I've had yet. The price should have been the first red flag, but I thought I was booking a VIP experience, so I was willing to pay extra. The bus itself should have been the 2nd red flag. As I said earlier, I am clearly an idiot. Approaching the bus, I realized it was very dirty. Elliot popped his head out from around the corner inside with a cheery smile, and his charming upbeat demeanor which gave me a small boost confidence this would be a good experience. We sat down and I realized that there was nothing VIP about what I had paid for. My plate had food crusted on it. The silverware was dirty. The "mocktail" was lukewarm. The food was stale and unpalatable. There were bugs swirling around the bus like a horse barn. We sat by the entrance, and the windows were covered in grime and finger prints. The tea was a joke. We got a small dixi cup amount of tea in our cups. The first was an herbal tea I could have picked up at Walgreens. The second was a peach tea that I suspect was crystal light or peace tea. The third was supposed to be a myer lemon tea, but by this point I was too sketched out to try it. The tour was not special or unique. I could have given the tour to my friend myself, and I've been to Chicago 5 times. Elliot was a good host, by the route was nothing special. The stops were simply timed by the flow of traffic. The lurching of the bus was not compatible with a high tea, and made for many funny and painful moments. Once Elliot fell on the stairs and another my friend burned herself. I could hardly talk to my friend about the tour because the speaker projecting Elliot's mating call was so loud, and when Elliot tried to walk up and down the bus the signal would cut out so he could only stand next to our table. At one point my friend pointed out that Elliot was singing from a YouTube karaoke video, which cut out when he got a text. I was really disappointed by this experience. I could have spent the money I spent on this on a real high tea, but thankfully we got some good laughs out of it.

    Even after so many negative reviews, bestie and I decided to give them a try. We believe in finding…read moreout for ourselves and not listening to hearsay knowing that each experience is different. The bus is so pretty and picturesque. Lots of PINK and pretty flowers everywhere. The table scape is beautiful and they serve Aqua Panna water, if you know, you know. We paid for the VIP selection which offers additional food and a glass of virgin Rose'. Mike our driver explained that we would have a 90 minute ride exploring Chicago. Eliot was our entertainer during the ride. He has a beautiful singing voice and would crack a joke or two. Lola was our beautiful tea hostess and made sure we tasted four different flavors. We each received a beautifully decorated plastic tumbler for our samples. Every single flavor was amazing! I do love a good tea. We started with Maple Apple Cider, Breakfast in Paris, Moroccan Mint and finished with a nice Chai. Again, each tea flavor was amazing! On to the food. The scones were good and came with clotted cream and preserves. VIP included lobster rolls. Smelled like fish but it was a pink spread, not good. Each finger sandwich had hard bread which seemed to dry out after being exposed to the air. Each tart that was supposed to have a hard crust was soft and mushy, not good. The deviled eggs had no flavor at all. Bottom line on the food, not good at all. Not sure how long it's sitting before being served. Everything that was supposed to be soft was hard and what was supposed to be hard was soft. Overall, the concept of a mobile tea party is great. Maybe find a way to cover the food. Get real lobster rolls.

    Photos
    Tea Around Town - Tea Around Town Chicago Experience

    Tea Around Town Chicago Experience

    Tea Around Town - Tea Around Town Food & Drinks

    Tea Around Town Food & Drinks

    Tea Around Town - Tea Around Town Bus in Chicago

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    Tea Around Town Bus in Chicago

    The 312 Limo

    The 312 Limo

    4.8(167 reviews)
    1.5 miWest Loop, Near West Side, West Town
    On-time commitment
    Beat or match prices

    I was on party bus duty for my daughter's recent high school dance. I priced out a few companies…read morewith party buses and 312 Limo was the most reasonable price. To be honest it was still a little expensive considering they were driving from Wilmette to Northfield to Glencoe, but less than the other: $840 for a 3 hour minimum for a party bus of 28. We also didn't need it for the entire 3 hours, but the options I found were either one way or 3-4 hour minimums so this was the best deal. I found their communication to be stellar both via email and text. The bus driver was on time and the kids had no trouble locating the party bus when they came out of the dance and I've heard it was one of many party busses. A few of my daughter's friends hopped on for the way home and commented that this bus was way nicer than the one they took to the dance from another company. Overall, it was a success. The parents could have easily driven these kids ourselves, but the party bus elevated the experience and the kids all seemed to enjoy the VIP treatment.

    I have used The 312 Limo company two years in a row for the Hinsdale Kitchen Walk and they never…read moredisappoint. They are always a little bit early, which is appreciate to load coolers, and snacks and the service is always top notch! They are my go to limo company for events, and I can't wait to work with them again in 2027.

    Photos
    The 312 Limo - Inside of trolley bus - red lights on top and color changing lights on ground, 1 small TV at front, two small areas for storing drinks/ice

    Inside of trolley bus - red lights on top and color changing lights on ground, 1 small TV at front, two small areas for storing drinks/ice

    The 312 Limo
    The 312 Limo

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    Gray Line Sightseeing Tours - historicaltours - Updated August 2026

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