Chicago Small Group Tour: Architecture & History
65 Ratings
Discover the best of Chicago's architecture, history, and local treats on this engaging small group walking tour. Join a knowledgeable local guide and explore the city's iconic sights and hidden gems.
Duration: 2 hours, 30 minutes
Cancellation: 1 day learn more
  • The Chicago Theatre - We start our tour under the dazzling marquee of the Chicago Theater (where you might recognize the neon sign from the movie musical Chicago) before heading off into the bustling city.
What's Included
  • Enjoy stunning river views
  • Friendly local English-speaking guide
  • A stroll through beautiful parks
  • Personalized recommendations for your stay
  • Discover Chicago’s iconic architecture
  • Savor Chicago-style popcorn, a local tradition
  • Taste chocolates from a renowned Chicago chocolatier
  • See the famous Chicago Theatre
What's Not Included
  • Gratuity
Additional Information

Chicago is a city complete with stunning architecture, delectable cuisine, and significant landmarks both historic and contemporary. This walking expedition takes you to some of the city’s popular locations with a resident tour guide, offering you insider knowledge on what sets Chicago apart from other cities. Moreover, we’ll include a few delightful local snacks to fuel you during the exploration.

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

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

Customer Ratings
(65 Ratings)
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Mar 17, 2024
Great architecture tour of Chicago - 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.
Review provided by Viator
Mar 17, 2024
Food, history & architecture - Great experience. We would definitely do it again should we come back to Chicago. Highly recommend the experience. It was an adventure doing the tour on St. Patrick’s Day which made it more fun.
Review provided by Tripadvisor
Mar 12, 2024
Dave’s Chicago tour - 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.
Review provided by Viator
Mar 9, 2024
Experience Chicago Architecture - 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.
Review provided by Viator
Feb 20, 2024
Very nice tour - 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!
Review provided by Viator
Feb 13, 2024
Great walking tour - 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.
Review provided by Viator
Feb 9, 2024
Dash-Best Tour Guide - Dash was the best tour guide I could ever imagine. He gave us so many unique stories and pointed out even the smallest of details that I wouldn’t have otherwise noticed as a regular tourist walking down the streets of Chicago. He was so knowledgeable about the city, it’s history, the cuisine and the best spots to have a great time. We were a group of 9 and Dash always made sure we had all the breaks and stops we needed to have a comfortable tour. Highly recommend, thank you Dash for an amazing time!
Review provided by Tripadvisor
Jan 31, 2024
Chicago Unveiled: A Dashing Detour with Delight - Forget the generic bus tours and skip the overcrowded tourist traps. If you're looking for a private tour of Chicago that ignites your senses and leaves you with memories that shimmer, then brace yourself for this tour. It's not just a sightseeing expedition; it's an exhilarating immersion into the Windy City's soul, orchestrated by a master storyteller named Dash. From the moment I met Dash, his infectious enthusiasm was palpable. He wasn't a walking encyclopedia spouting facts; he was a passionate local weaving tales of hidden gems and forgotten corners. We strolled through sun-dappled alleys, where vibrant murals whispered stories of resilience, and stumbled upon quaint squares tucked away from the urban clamor, humming with a quiet charm. Dash's itinerary wasn't rigid; it danced to the rhythm of my curiosity. He detoured at the whim of a captivating storefront, delving into the history of Chicago's artisanal scene. Dash wasn't just my guide; he was my confidante and curator of unforgettable experiences. He recommended hidden treasures – a jazz room buzzing with local talent, a rooftop bar with breathtaking skyline views... By the end of the tour, Chicago wasn't just a city; it felt like a secret sanctuary, revealed by a trusted friend. Dash didn't just show me the sights; he unlocked the city's hidden heartbeat, its warmth, its grit, its undeniable magic. His tour wasn't just a tour; it was a portal to a Chicago that most tourists never see, a city that whispers its secrets to those who dare to listen. **Five stars, with a dash of magic dust.**
Review provided by Tripadvisor
Jan 8, 2024
Very detailed information about the city. Good! - The treats the guide offered to us. It was very kind of Rich and we would do it again if we came back.
Review provided by Viator
Nov 29, 2023
Learn about some incredible buildings - 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.
Review provided by Viator
Select Date and Tickets
up to 15 guests
1 Adult
May 2024