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    Inside Chicago Walking Tours

    5.0 (108 reviews)
    Open 9:00 am - 6:00 pm

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    The Rookery
    kris r.

    We had a wonderful and informative tour given by Adam. We are both Chicagoans and learnt a lot about Chicago architectural and general history. So much interesting information. Looking forward to going on another tour from this group.

    Ease of booking Pleasant customer service Tour guide Kaylee excellent Extremely knowledgeable and interesting

    Kylie, as a tour guide, is animated but loud and clear in her delivery.
    Ron O.

    As the tour guide, Kylie was very knowledgeable and, most importantly, a great and pleasing personality that made the tour educational and pleasant despite the biting cold! (We're from California!) Also, we were running late because of the Chicago BOA Marathon, but Hillary from the tour office ensured we did not miss our tour. She and Kylie coordinated so we could still join the tour despite being 20 minutes behind.

    Tiffany Ceiling - The ceiling showcases elaborate decorative patterns with three prominent blue oval sections, each surrounded by intricate white and gold detailing. The design includes ornate borders and symmetrical motifs, with two hanging light fixtures visible. The perspective is from directly below, emphasizing the ceiling's ornate craftsmanship and symmetry.

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    8 months ago

    Heath was a great tour guide. He was kind and extremely knowledgeable. His pacing was great and we had a lot of fun.

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    2 years ago

    Colleen our tour guide did great and is an Improv comedian. Very knowledgeable and fun.

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    3 years ago

    Great informative tour of one most interesting buildings in Chicago. Adam was fantastic!

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    Page 1 of 3

    Ask the Community - Inside Chicago Walking Tours

    Review Highlights - Inside Chicago Walking Tours

    Five friends came with me today on a private 2-hr tour of a slice of Chicago with Hillary from Inside Chicago.

    Mentioned in 47 reviews

    Read more highlights

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    Chicago Architecture Center

    Chicago Architecture Center

    (811 reviews)

    The Loop

    Chicago Walking Tour - Elevated Architecture Downtown 'L' Train…read moreWe have previously taken the CAC boat tour and one of the surface walking tours (both of which were great), but this time we wanted something with a slightly different perspective while staying downtown. We chose the Elevated Architecture Downtown 'L' Train tour led by Andrew, our CAC docent. As no one else had signed up for the tour that morning, it became a private tour. Andrew was not only very knowledgeable about the architecture and friendly, but also, given that he works in planning at the Chicago Metro, was able to take us on an even deeper dive concerning the "L", its history, and some of the current challenges. As we were about 35' about street level for the tour, we were also treated to a different perspective of the building and their design/decoration, something that cannot be readily observed from street level. Thans again to Andrew for an information and entertaining tour above the streets of downtown Chicago-truly a unique experience.

    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)

    Chicago River Boat Architecture Tours - Our boat

    Chicago River Boat Architecture Tours

    (281 reviews)

    Near North Side

    Every person I asked for a suggestion about what to do when in the city and everyone said to take…read morean architecture tour. They were right. I paid for the Gropuon which made our tickets half price. The one thing Is will say is that the parking directions for were confusing to me - I could have parked much closer but ended up going to the wrong location. This was something the tickets warned about but I just didn't figure it out. There was a bar and food on board but I didn't partake. We decided to do the nighttime tour per the suggestion of those who told me about the tour and I'm happy to have done so. The buildings were so beautiful and the lights were great. Next visit I will try the day time tour. It was an excellent way to spend 90 minutes and learn some really cool facts about a great city. I highly recommend it to anyone visiting Chicago.

    Chicago riverboat architectural historical tour on main branch of river. Time to cruise…read more Nonstop 90 minutes. Talk about the architectural sky scraper wonders. foremost. Mind blowing enormously tall. Alot of humor and details on rental price @$400,000 a year. Famous people like Barack Obama and Oprah Winfrey lived here. Willis seats tower 100 stories tall 1,052 in the Windy City Sky! It's the tallest! there are 37 drawbridges on the main branch river. That's all the facts in my head could remember. The river is alive! The buildings taller than Sequoia redwood trees or Oregon Douglas Fir. Glass, concrete and steel in assorted shapes - seemingly alive like a living tree. I feel the energy of the river and the buildings standing tall. Worth the moolah.

    Chicago Boat Company - Celebrating her!

    Chicago Boat Company

    (180 reviews)

    Near North Side

    One Facebook ad, quick online reservation, and here we are Thanksgiving weekend floating down the…read moreriver in a hot tub in 20 degree weather...AND we would do it again! Here's what to know: -Make the reservation online days or weeks in advance so everyone can complete/sign waivers online well in advance -A couple of days before your date, the person who made the reservation will receive a text w/ additional waiver to sign and a training video on safety. Complete prior to date as it reduces the amount of time to check-in -Yes, they do ask for the credit card that was used to pay for the reservation, their ID, and they have to be at check in -There are a lot of fees for misuse and misconduct so definitely read the documents -once checked in, a team member walks you to the marina area and the changing rooms; the bathrooms are near the changing area and require a key to enter -The bathrooms and changing area are heated -The changing area has a few lockers to keep your belongings safe and you are responsible for keeping the key (if you lose there is a fee) -Once in your bathing suit, keep your shoes on, warm hat, and jacket -The boat doesn't have areas to keep your stuff so keep most of your items in the locker -A team member will walk you to your boat and there is a covered plastic crate that you will put your coat, locker key, and shoes in -There is a walkie talkie on your boat so you can stay connected w/ your assigned team member -The water is very warm and you can control the heat off/on -Make sure the entire group pays attention to how to drive the boat, it's def a team project -The boat doesn't not go very fast but turns seamlessly so give yourself grace for figuring how it maneuvers -Yes you are on the water w/ big water taxi boats and tourist boats; they definitely make waves and will push your boat out of their way -You can drive the boat w/in a 5 block radius -We had the most fun just floating in one of the "pier" type areas; sooo many people bundled up walking near the river said hi, took pics of us, and asked about our experience -You will stay warm the entire time, it was sooo hot sometimes we stood up just to cool off If you are thinking about this experience just grab some friends and do it! We are already talking about doing it again and bringing some friends!

    When I asked if I wanted to cruise down the Chicago River in the middle of February, I first…read morethought my husband had lost his mind. However, once I saw the hot tub option I decided to be open minded and boy am I happy I did. The company has great communication and Devante, our crew member, was very helpful and friendly. We had 90 minutes but honestly because you can only cruise between a bridge span of three blocks we came back early. Just know that you are the one driving the boat so you definitely have to take somebody who is willing to be the designated captain. Overall, a really fun experience and I would try it again in the summer..

    Inside Chicago Walking Tours - architecturaltours - Updated May 2026

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