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    Inside Chicago Walking Tours

    5.0 (112 reviews)
    Closed 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.

    Henry was an amazing guide. He brought his passion for architecture and engineering to our Art Deco tour, showing us the optimism and opulence of the era. I can't recommend this tour enough.

    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

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    2 months ago

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    10 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

    Kylie took us on a GREAT tour of stunning buildings. Highly recommend this tour for non-architecture people.

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

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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 48 reviews

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    Chicago Architecture Center

    Chicago Architecture Center

    4.8(816 reviews)
    0.6 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?

    Wendella Tours & Cruises - Chicago River Architecture Tour

    Wendella Tours & Cruises

    4.4(1.6k reviews)
    0.7 miNear North Side

    First time on the architecture boat tour on the recommendation of a bunch of friends who had…read morealready taken the tour in the past. Personally, I was pleasantly surprised. The words "architecture" and "boat tour" don't immediately spell a fun time in my mind. But this tour is 1) a pleasant way to see the center of Chicago from the water, 2) actually interestingly informational, as the tour guides are extremely on top of their game, 3) much more dense that you expect (these guys are talking non-stop), and 4) surprisingly good views, especially when you get all the way out into the edge of the harbor! Finding the place was a bit roundabout, but once we got there, staff were super friendly, and it was easy to get on the boat and off to our next stop afterwards. Parking suggestions on the site are solid too. I'm not sure whether I'd do it again, but I'd definitely recommend it as a must-do stop on any visit!

    90 minute Architecture tour…read more It was a cloudy, windy, and cold day in June. Even with the clouds rolling in & out and blocking a lot of the views it was still interesting and our awesome guide, Bobby, was knowledgeable, funny, and kept it interesting and flowing for adults and kids. The tour starts on the river heading towards Lake Michigan. The ride into the lock was a little lengthy as we had to wait for them to fill it with boats first. Once we made it onto Lake Michigan it was very chilly, but I'd rather be freezing than sweating like crazy on a hot humid day. We were on a smaller boat which was nice. - upper deck: Seats long the outside and chairs in the middle. Only wish they had cushions. - lower deck: had some small seating outside and standing bar tables - lower deck: indoor restrooms and bar area - snacks, drinks available for purchase If rain is in the forecast bring paper towels to clean off your seats. I also saw some people with Wendella rain ponchos, but not sure where to get them? Really fun and beautiful way to see the city! Highly recommend!

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    Wendella Tours & Cruises
    Wendella Tours & Cruises
    Wendella Tours & Cruises

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    Chicago Water Taxi - Chicago Water Taxi has stops on all three branches of the Chicago River.

    Chicago Water Taxi

    4.2(167 reviews)
    0.6 miMagnificent Mile, Near North Side

    Took the taxi several times during my trip!…read more Affordable at $10 per one way ride. Covers a long ground. Nice, quick ride to Chinatown with ample seating available. Honestly a great alternative to the architecture tour, which I did also and didn't enjoy due to crowdedness.

    I found out about the Chicago water taxi on TikTok. It was $10 one way, $20 for round trip. I got…read morepicked up on Michigan Ave to go to Chinatown. It was quite unorganized and the young people working there at the podium's were cackling & playing around, which was a little annoying. I was told that there was no guarantee I would get a ride if the boat was full, but I could get in line and see if there was room. I was able to board & pay on the boat with ease. It was pretty easy to get tickets on board by the cashier. The ride there was smooth with no issues, I sat down below. That boat had AC which was nice on such a hot day. We docked and I walked to Chinatown. I was only there for about half an hour before having to return to the city. The second boat was not air conditioned but there was a breeze. Overall I had a nice experience. I'd definitely recommend taking the water taxi to get across town. It's affordable yet scenic if you don't want to do the traditional architectural boat tour. The only thing I'd recommend is having a few more time slots.

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    Chicago Water Taxi - Chicago Water Taxi operates on a fixed schedule from March through December.

    Chicago Water Taxi operates on a fixed schedule from March through December.

    Chicago Water Taxi - Chicago Water Taxi is a fleet of four iconic yellow and black vessels.

    Chicago Water Taxi is a fleet of four iconic yellow and black vessels.

    Chicago Water Taxi - Tickets can be purchased online, at any Wendella ticket office, or on the vessels.

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    Tickets can be purchased online, at any Wendella ticket office, or on the vessels.

    Inside Chicago Walking Tours - architecturaltours - Updated July 2026

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