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    Inside Chicago Walking Tours

    5.0 (113 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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    12 days ago

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    11 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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    2 years ago

    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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    Wendella Tours & Cruises - Chicago River Architecture Tour

    Wendella Tours & Cruises

    4.4(1.6k reviews)
    0.7 miNear North Side

    My family and I had such a wonderful time with Wendella Tours and Cruises! Even though the weather…read morewasn't perfect, it actually made our adventure even more special. The friendly and knowledgeable staff went above and beyond to make us feel comfortable, including cleaning the seats for us. Our tour guide was so well-informed and kept us dry, which was really impressive. They even had $5 rain ponchos for sale. The boat had two floors, and those who preferred a more private space could also buy drinks like free spirits and alcoholic beverages. Since this was my very first trip to Chicago, I definitely want to join the tour again. The price was fair, the staff was warm and welcoming, and the relaxed atmosphere made the whole experience even more enjoyable. Plus, I learned so much! Overall, my family had a fantastic time, and we wholeheartedly recommend it!

    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!

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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(169 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.

    Photos
    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.

    Shoreline Sightseeing - Chicago Fire Department near Navy Pier

    Shoreline Sightseeing

    4.7(1.9k reviews)
    1.0 miNear North Side

    Eric was a very good speaker and staff war very nice, the entire thing was very informative thank…read moreyou guys so much!

    This tour was on the top 10 list of our things to do in Chicago. I researched all the boat…read morecompanies that offered the Chicago architecture boat cruises and Shoreline Sightseeing came out hands down #1 for us in tour length, type of cruises, accessibility and in price for what you got. Best deal. Our tour guide was happy, energetic, and very knowledgeable about Chicago because he was born and raised there. We chose the 75 minute, 4pm Chicago River tour and it covered a lot! We never lost interest and learned about Chicago's history. It is well worth it! Our Architecture River Tour boat departed from the dock at Navy Pier. We learned that their boats are the most accessible at this location. Their boats can accommodate wheelchairs up to 30-inches wide. Your wheelchair must be able to navigate a ramp with a 2-inch step at one end. I needed one that was kind to my knees. Best to call them for more details. They were very helpful whenever we called them. Their boats are both double-decker and single-level boats, and there is generally no protection from the sun, rain, or wind. There is a small bar on the main level. Restrooms are located on the lower deck, which is accessible only via stairs from the upper deck. Enjoy! It's amazing!

    Photos
    Shoreline Sightseeing - The Chicago Architecture Tour boat cruise was amazing!

    The Chicago Architecture Tour boat cruise was amazing!

    Shoreline Sightseeing - Top deck - guide Joe

    Top deck - guide Joe

    Shoreline Sightseeing - Merchandise mart

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    Merchandise mart

    Chicago River Boat Architecture Tours - Our boat

    Chicago River Boat Architecture Tours

    4.7(291 reviews)
    0.8 miNear North Side

    Such a great city for architecture, the very oldest building sitting next to the newest…read moreskyscrapers. I loved this tour...even though it rained and we had to spend part of the tour inside to stay dry without much of a view, it was still a great tour for the cost. We were warned to make a reservation cause the tours do fill up, and this was a holiday weekend. Do not leave Chicago without doing this!

    There are many different boat tours out there with different prices and different lengths of time I…read morewould definitely recommend the architect boat river tour. I would say if you have 90 minutes this boat tour is a must do. I believe the option times that we had to choose from was anywhere from 10:00 a.m. for the first boat going out and the last boat was 4:00 p.m. but check the website for exact times. We booked our tour online to make sure that we got the time and date that we wanted to we preferred earlier in the day. We booked about 2 months out. These tours fill up quickly especially in the summer time. We started lining up about an hour before to make sure we got a seat up top so we could enjoy the view. If you prefer to sit inside you still will be able to hear the tour guy just you may not be able to see everything he is announcing it may be on the other side of the boat which you may not see if you're inside because of other people that are sitting. Our tour guide was wonderful explaining the different buildings and if you had any questions he would definitely answer those questions later on. This was my second time in Chicago I learned many new things by going on the tour I am glad that I did and I would recommend anyone else to do so as well.

    Photos
    Chicago River Boat Architecture Tours - Boat top floor

    Boat top floor

    Chicago River Boat Architecture Tours
    Chicago River Boat Architecture Tours

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    Inside Chicago Walking Tours - architecturaltours - Updated August 2026

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