Chicago Loop Walking Tour: Modern Skyscraper Exploration
33 Ratings
Embark on a captivating walking tour of Chicago's Loop district, exploring modern skyscrapers and iconic landmarks. Discover the Fine Arts Building, Harold Washington Chicago Public Library, Marquette Building, and more. Don't miss the stunning Tiffany mosaic at Macy's and the world's largest Tiffany dome at the Cultural Center. Book now and make it a full day with our Pedway or Historic Pubs tour in the afternoon!
Duration: 3 hours, 30 minutes
Cancellation: 1 day learn more
  • Fine Arts Building - Meet your guide in the lobby and tour this famous building, which still has manually operated elevators.
  • Harold Washington Library Center - Check out the library’s hidden gems and exhibits.
  • Monadnock Building - Take a close-up look at what was once the largest office building in the world.
  • Marquette Building - Learn about this national landmark.
  • Revival Food Hall - Take a quick break and grab a snack at one of Chicago’s first food halls. (Refreshments not included in tour price.)
  • The Rookery Building - Take a quick look at one of the most architecturally-significant buildings in the city.
  • Quincy - Board the L train for a quick trip to our final two destinations.
  • Macy’s on State Street - Visit this iconic department store and marvel at its amazing architecture.
  • Chicago Cultural Center - Wrap up the tour with a quick peek at the home of the world’s largest Tiffany dome.
What's Included
  • Transit tickets
  • Local expert guide
What's Not Included
  • Gratuities
  • Food and beverages
Additional Information

Our journey begins at one of the Loop’s most captivating structures — the Fine Arts Building. Initially constructed in 1884 as an exhibit space and office complex, it was later restructured for its current use.

Next, we make our way to the Harold Washington Chicago Public Library, which was the prize-winning design in a contest for a new library blueprint. From there, we take in the sights of three landmarks from the late 1800s, followed by the stunning Marquette Building, the Field Building (erected on the first modern skyscraper’s grounds), and the exceptional atrium lobby of the globally recognized Rookery Building.

Then, we proceed to the charmingly renovated Quincy L stop (an original 1897 design) to board the train to our final destinations. We explore the iconic Macy’s to admire the splendid Tiffany mosaic and conclude our trip at the Cultural Center, home to the world’s most extensive Tiffany dome.

Enhance your day further by booking our Pedway or Historic Pubs tour for the afternoon!

  • Should be able to climb stairs as not all train stations are equipped with elevators
Fine Arts Building
South Michigan Avenue
Meet your guide in front of the building at 410 S Michigan Ave entrance.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
(33 Ratings)
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1 star
Dec 24, 2023
Excellent historical/ architectural tour! - Tom was extremely knowledgeable about the city and the buildings and related history. He took us in some fascinating buildings and had loads of stories. I lived in Chicago for a number of years in the 70s and still discovered how much I didn't know! I would recommend it to anyone who wants to learns something about Chicago.
Review provided by Tripadvisor
Nov 30, 2023
Stop, don's pass up this opportunity!! - This was a tour that I set up for my husband, he loves architecture and I just went along. I am so glad I did, I learned so much from Tom. You could tell how much the history meant to him and he being able to share it with us. We went all over. We walked at a leisure pace with several bathroom breaks. I promise you will walk away from this tour smarter than we you started. They also have several other tours on their website
Review provided by Tripadvisor
Oct 9, 2023
Thank you, Tom, for deepening our 5 day visit so very much. - We are two architecture-fascinated folks from Oregon and NYC. Thanks to Tom's Skyscraper Tour (am) and Pedway Tour (pm), we have another home away from home. The morning was full of memorable sitings and explanations, never dull nor trudging. The Pedway tour surprised us for its urban usefulness and pop-to-beautiful-surfaces creativity. The following 4 days of our stay illuminated L Stop's excellent guidance: we were ever saying, "we saw [that building] yesterday...that's the building which Tom said [ ]...we're going [ ]; we can use the Pedway!" This is not the typical canned tour routine. Tom knows his city from the idiosyncratic details to the soaring structural beauties, and conveys his knowledge with personal attention to our interests. Enjoy!
Review provided by Tripadvisor
Jul 6, 2023
Awesome experience for tourists and locals alike - This was a fantastic tour where we really learned a lot. Tom, our tour guide, led the tour at the perfect pace and was incredibly knowledgeable at every stop along the way. He answered our questions thoughtfully and really made the tour feel personal. I would definitely go on another tour with L Stop Tours!
Review provided by Tripadvisor
Jul 5, 2023
Learned so much about Chicago architecture! - Tom was so knowledgeable! Any questions we had, he knew the answers to. This was so much fun. Great idea for taking out of town visitors.
Review provided by Tripadvisor
May 17, 2023
Perfect tour for part of the day - All four of us (adults) really loved this tour. Decent amount of walking, short ride on L-train, and so cool to see inside of some of these 'modern' skyscrapers. Our guide Tom was knowledgable, friendly, and provided interesting information - you could tell how much he loves, appreciates Chicago (and we felt that way too). He let us tailor the tour a bit - a longer lunch break at Revival food hall - great, local foods - and quick trip into the Money Museum. All so good. Looking forward to going back and doing one of the other tours offered.
Review provided by Tripadvisor
May 13, 2023
Great tour - Really great tour. Tom our guide was knowledgeable, personable, tailored the tour to our interests. Highly recommend. Perfect amount of walking, attractions, and information. Rock chalk!
Review provided by Tripadvisor
Apr 8, 2023
Recommended tour to start your Chicago vacation! - We had so much fun! Tom was very attentive and knowledgable and he showed us a bunch of extra spots around town, he has so much love for the city of Chicago and made us love it too!
Review provided by Tripadvisor
Apr 5, 2023
Best of Inside and Out - What a wonderful day! Loved getting to visit many different building and see the inside of the buildings as well. We also enjoyed getting to do a quick ride on the "L" train. The stop for a snack was also great.
Review provided by Tripadvisor
Mar 25, 2023
More than just a walking tour - get inside these buildings - Fantastic city tour showing off the fabulous interior of the great buildings in Chicago. So different getting inside these buildings with a a very knowledgeable guide. Thanks to Tom for showing us such a different perspective of Chicago. Highly recommended .
Review provided by Tripadvisor
Select Date and Tickets
minimum 2 guests
up to 10 guests
April 2024