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Inside Chicago Walking Tours

5.0 (115 reviews)
Open • 9:00 am - 6:00 pm

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William G.

I have taken many tours in different cities at home and abroad. Chicago being the birthplace of the modern skyscraper has many stories to tell about the evolution of turn of the century architecture after the great Chicago fire. Locally we have a great city guide on our local PBS channel 11 who does a fantastic job at uncovering some of the best forgotten stories about our cities past. Of course, I am referring to Geoffrey Baer, whom I have watched on our local PBS many times over the years. So yes, I can say that I am a fan. But you know it's one thing to watch these architectural marvels on TV or in person. I decided to be a tourist in my own city by taking the Original Chicago Architecture Interiors Tour by Inside Chicago Walking Tours. How was it? I loved it. Many of the treasures we uncovered, I have walked by for many years without every going inside and seeing the marvelous interiors firsthand. We also went over the exterior of several buildings that I never stopped to think about the stories behind the buildings history. Yes, I took a lot of buildings for granted. On this tour we went over the timeline and historical evolution of some of some of the significant buildings in our downtown area. Of course, were not able to cover all of them because Chicago is blessed to have so many great buildings with a storied past. I highly, highly recommend this tour to tourists and locals alike. Some of the buildings that were covered were the Chicago Board of Trade, The Federal Building, The Marquette, The Palmer House, and the Chicago Cultural Center (and many more). If you decide to take this tour get ready to be wowed and enlightened about Chicago.

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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2 months ago

Not just architecture facts, good intro or review of Chicago generally. Henry met us on time, was very clear and paced the tour perfectly.

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6 months ago

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8 months ago

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29 days ago

We just loved our guide, Heath. He was so knowledgeable about tour. Would definitely recommend this tour to friends.

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1 year ago

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6 months ago

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9 months ago

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9 months ago

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1 year 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

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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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4 years ago

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4 years ago

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3 years ago

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

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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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Almost everyone you meet in Chicago who loves their city will ask when you tell them you are…read morevisiting from out of town, "Have you done the architectural boat tour?" People in Amsterdam will also ask if you have done a canal boat tour - and you have to do these when you visit these cities. Our docent volunteer guide, Steve, was excellent. He was very personable and extremely knowledgeable about the city's riverside buildings and its history. The boat staff was also hardworking and ready to help with any issues, from getting a drink at the boat's downstairs bar to handing out covers when the rain hit us. For what we paid, the 1.5 hour tour was more than worth it. I recommend sitting at the top towards the back, as you don't have to crane your neck as much when he points out places of interest. This was a truly wonderful experience and I would do it again in a heartbeat.

Not what I expected overall but it was still a very educational experience. Scoring tickets to…read moreChicago's Architecture Center through our hotel, we used the tickets as a good time filler. Not a must see or do attraction but a great day filler activity as you explore the city. Loved the wealth of information they offer as it's valuable to understand Chicagos importance from the ground up! I thought it would be more about highlighting the amazing architectural buildings around the city but nothing like that. It's was more about the environmental impact the city has and the hurdles when designing buildings around town. The staff were friendly at check in and provided great service overall as they were kind and helpful. Small center that you may explore at your own pace and may or may not be worth the admission price. But scoring free tickets it allowed us to be selective in our day or day plans to include the activity to pay it a visit!

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Chicago Architecture Center - The stunning Drake Family Skyscraper Gallery on the 2nd floor of the CAC.

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Chicago Architecture Center - The Chicago Architecture Foundation River Cruise aboard Chicago's First Lady Cruises is consistently voted the #1 tour in Chicago.

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4.2(174 reviews)
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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.

If you're looking for a fun and unique way to explore Chicago while getting from one destination to…read moreanother, I would definitely recommend the Chicago Water Taxi! We decided to take the water taxi from the Chicago Riverwalk all the way to Chinatown, and it was such a cool way to experience the city from a different perspective. Rather than taking an Uber or using traditional public transportation, we figured why not enjoy the scenery along the way? Before boarding, one of the employees informed us that the ride to Chinatown would take approximately 45 minutes. However, in my opinion, it felt much closer to 30 minutes! Either way, we weren't in a rush, and Chinatown was our first stop of the day, so the travel time wasn't an issue for us at all. The ride itself was enjoyable, and being able to see the city from the water made the journey feel like a little sightseeing excursion rather than just transportation. Plus, at only $10, I thought it was a great value for the experience! Overall, I would absolutely recommend the Chicago Water Taxi, especially if you're planning to visit Chinatown from the Riverwalk and have some extra time to spare. My advice: If you're not in a rush, skip the usual transportation and take the scenic route! It's an affordable, relaxing, and memorable way to see another side of Chicago.

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

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We did the 75-minute Architecture River Tour with Shoreline Sightseeing, departing from Michigan…read moreAvenue, and it was such a great experience! If you're visiting Chicago, this is definitely an activity I would recommend adding to your itinerary. The tour was incredibly informative, and it was fascinating learning about the city's history, architecture, and the stories behind some of Chicago's most iconic buildings. Seeing the city from the water also gives you an entirely different perspective, and the views of the skyline were absolutely beautiful! Our tour guide was fantastic! He was knowledgeable, personable, and had a great sense of humor. He kept everyone entertained with jokes throughout the tour while still providing plenty of interesting information. I really appreciated that balance because it made the experience feel less like a history lesson and more like an enjoyable conversation. The 75 minutes went by surprisingly quickly, and it was such a relaxing way to take in the city while learning something new. Overall, this was definitely one of the highlights of our Chicago trip! Between the beautiful views, interesting history, and entertaining tour guide, it was a wonderful experience from start to finish. Absolutely worth doing, especially if it's your first time visiting Chicago!

A river tour is a must when visiting Chicago! We decided to do Shoreline Sightseeing, and it was…read moresuch a great experience. We were nervous because my mom gets motion sickness easily, and we weren't sure she'd be able to enjoy the tour. Thankfully, the water was calm enough, and she absolutely loved it! The views were beautiful, and we learned so many fun facts about the city along the way. Definitely recommend adding this to your Chicago itinerary!

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Shoreline Sightseeing - Top deck - guide Joe

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Inside Chicago Walking Tours - architecturaltours - Updated November 2026

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