Chicago: Architecture, History & Highlights Small Group Tour

Badge of ExcellenceChicago, USA
Best of Chicago History and Culture Tour with Chocolate and Popcorn
Likely to Sell Out

From $59.00

Select Date and Travelers

up to 24 hours before the experience starts (local time)

  • 2 hours 30 minutes (approx.)
  • Mobile ticket
  • Offered in: English


The Windy City is known for its spectacular architecture and eclectic food scene. Experience both on this tour through the downtown that combines sights with nibbles. Take in famous landmarks like the Chicago Pedway, City Hall, Picasso Sculpture, Chicago Riverwalk, Wrigley Building, Tribune Tower, Magnificent Mile, Millenium Park, and Cloud Gate on foot. Learn about the history of some of Chicago’s most well-known buildings while enjoying views of the Chicago River. Taste surprise local treats from two beloved city eateries during the tour.
  • Experience the beauty of some of Must-See spots in downtown Chicago in just a few hours with a local guide.
  • Immerse yourself in the best of Chicago culture and discover why Chicago’s art, food scene, and architecture is one of a kind.
  • Enjoy a couple of classic made-in-Chicago snacks like Chicago-style popcorn and homemade chocolate.
  • Personalized attention on small-group tour (or private) for just 16 people or fewer.
  • This tour is carbon neutral, operated by a B Corp certified company committed to using travel as a force for good.

What's Included

  • Discover Chicagos’ incredible architecture both old and new
  • Taste locally made chocolate from a Chicago staple
  • Taste local tradition: Chicago-style popcorn
  • Enjoy stunning river views
  • Pass by where Chicago Theatre where musical Chicago was filmed
  • A stroll through the beautiful parks
  • Join Friendly Local English-speaking guide
  • Get tips on what else to see, do and eat during your stay
  • Gratuity

Meeting and Pickup

Meeting point

  • The Chicago Theatre
    175 N State St, Chicago, IL 60601, USA

    The Chicago Theatre (underneath the marquee), 175 N. State Street, Chicago, IL 60601

End point

  • Millennium Park, Chicago, IL, USA

    Millennium Park and Michigan Ave

What To Expect

Additional Info

  • Confirmation will be received at time of booking
  • Wheelchair accessible
  • Stroller accessible
  • Service animals allowed
  • Near public transportation
  • Transportation is wheelchair accessible
  • Most travelers can participate
  • This is a child-friendly tour. Children under the age of 6 are permitted to join this tour free of charge.
  • Experiences happen rain, shine, or snow. Please dress accordingly.
  • Suitable for all ages and fitness levels, but please note that this tour covers about 4.8 km (3 miles) of walking.
  • We can accommodate vegetarian options but cannot accommodate other food allergies or dietary preferences. Please notify us in advance if you have any dietary requests.
  • Note that the Bean sculpture is under construction until Spring 2024 and views will be limited.
  • This tour/activity will have a maximum of 16 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.

Traveler Photos

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66 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 66 reviews
Trivia Walk instead of Architecture Walk
David_S, May 2024
Really nice guy but no real insights into architecture. Just a nice walk with some info about when buildings were built and what they were used for. I was hoping to really learn about their architects and architectural decisions. This was more of a “trivia” walk. If you’re going to do this, don’t do it after you’ve already been in the city for a few days as you will just touch in most highlights that you already naturally pass by.
Wonderful Private Tour
Ligia_P, Mar 2024
Our guide, Kevin, was very nice, knowledgeable, and catered the tour to our interests since it was just me and my friend. We especially loved a return visit to the Art Institute (which we had visited the day before but had managed to miss seeing the Monets, Van Goghs, and other important works). We also enjoyed the walking tour in the downtown Loop area, including seeing the Chicago River and the Merchandise Mart Building. I have a bum knee at the moment and was worried about a walking tour, especially stairs, but Kevin was mindful of the situation and we went slowly. My friend and I asked many questions and learned a lot -- I went home afterward to read up on Richard Nickels and his tragic death giving rise to the architecture preservationist movement in Chicago. Thanks, Kevin, for a great tour!
Great architecture tour of Chicago
Eric_S, Mar 2024
It was a great and informative tour. Really learned a lot about the culture and architecture history of the city. The chocolate and popcorn tasting was an additional plus.
Dave’s Chicago tour
marymtait, Mar 2024
The buildings and their architectural history. Dave was an excellent guide! He was a very comfortable person. I felt free to ask any questions and to ask for more info.
Experience Chicago Architecture
LeviJames_D, Mar 2024
The walk tour is something not to be missed for three reasons, especially when you’re on a short trip. Our guide, “tall Dave”, knows a lot about the history of the places we visited, shows interesting photos, and makes sure everyone is well accommodated. The sites have very fascinating architecture, some of them are hidden gems that do not usually appear in top places to visit when you Google. Finally, the group is pretty small, hence, it’s easier to interact with the guide, ask questions, and have fun with fellow tourists. So if you’re planning to visit Chicago, this tour should be in your checklist.
Very nice tour
Isadora_K, Feb 2024
We can see most of the main landmarks of the city, which has an impressive architecture and it is beautiful! Guide Rich is very attentive and helpful, a lovely person!
Great walking tour
Marla_O, Feb 2024
Our guide, Dash, was very informative and really got a lot in during our 2.5 hour tour. It was a little crisp out but he did a good job getting us inside as needed to warm up. I’ve spent a decent amount of time in Chicago but never really taken the time (except for a river tour) to look closely at the buildings. It was nice to slow down and take them in. The only negative was pre-trip when I had to jump through hoops to get another person added to our private group. They eventually accommodated.
Very detailed information about the city. Good!
Esteve_A, Jan 2024
The treats the guide offered to us. It was very kind of Rich and we would do it again if we came back.
Learn about some incredible buildings
Craig_R, Nov 2023
I was very lucky to be the only person on the tour which was probably because it was a very cold day. The temperature did not get above freezing. Dave the tour guide was very friendly and we spent a pleasant time walking around Chicago looking at the outside and inside of some amazing buildings. Dave knew his stuff and had plenty of interesting anecdotes. A good starter to Chicago architecture.
Worth it.
William_T, Nov 2023
Rich was a great guide. Courteous, knowledgeable and witty. A very enjoyable walking tour, great sights.
Don’t just see the outside of buildings.
Charles_H, Oct 2023
Very knowledgeable guide who’s enthusiasm for Chicago is contagious. The ability to walk inside buildings, see the remarkable details you won’t see from outside, and learn the amazing history of Chicago were outstanding.
Katharine_H, Sep 2023
Guide read from phone a lot but route was ok and there were some pleasant surprises - popcorn and chocolate. Quite expensive in comparison to recent tours in other places.
Perfect intro to Chicago!
Shenea_H, Aug 2023
Kevin(from the chi) was an amazing tour guide. So knowledgeable and enthusiastic. The mix of history, architecture and local art and sweet/savory treats made this the perfect introduction to Chicago!!! The tour definitely did not feel like 2.5hrs. In fact I didn’t want it to end!! I got lucky with this last minute booking because it was such a small group so we became fast friends by the end of my excursion. I will definitely recommend this excursion in the future and for sure will recommend touring with Kevin!
Chicago Dave is the best!
Tiffany_C, Jul 2023
Chicago Dave was a fantastic tour guide! My cousin and I were with a small group of international people from France to Alabama. He made us all feel like rockstars! Thanks Chicago Dave!
Had a wonderful tour....
Garth_H, Jul 2022
Had a wonderful tour. Great mix of history, architecture and food, not too long and had sufficient rest stops.
Amy_H, Oct 2021
Our tour was changed a few times but I have no doubt it turned out exactly how it was supposed to. We ended up havimg Kelly as our guide (this was a change) and she was phenomenal! Her knowledge, stories and insights of the city were so intriguing! My only suggestion for her is a list of suggestions even if she emailed it text it to those interested after the tour. She was SO GOOD at trying to personalize each group with where we were staying but she had SO MANY good suggestions it was impossible to remember them all. She was truly fantastic though!
Wonderful tour!
Brenda_B, Sep 2021
The amazing architecture and history of the city was amazing. Our guide, Kevin, did a wonderful job with so much enthusiasm!
Great Chicago tour!
Robyn_S, Aug 2021
My fiancé and I had a fantastic time on this tour! Lara was our tour guide and she was fantastic! Such a great personality and so knowledgeable regarding the city Chicago! We had so much fun! Highly recommend!
Enjoyable walking tour.
Kathleen_L, Aug 2021
Kelly was a very knowledgeable and personable guide. Learned many fun facts about the Windy City. One improvement would be headsets to block out street noise and make it easier to hear the guide.
Informative AND fun!
Laura_K, Jul 2021
We’ve been to Chicago many times, but this was the first time we’ve gone on a tour. Wow! Certainly worth it! We learned so many new and exciting things that we’ll definitely be utilizing in the future. The guide was very informative, but he also made everything fun. The flow was perfect and we got a great mix of history, architecture and fun facts. Great time!

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