Guided tour

Chicago: History, Culture and Architecture Walking Tour

Guided tour

Chicago: History, Culture and Architecture Walking Tour

From US$ 59 per person


Take a private or shared group walking tour of some of Chicago’s greatest hits: incredible architecture both old and new, delicious local treats, stunning river views, and much more.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
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Covid-19 precautions
Special health and safety measures are in place. Check your activity voucher once you book for full details.
Duration 2.5 hours
Check availability to see starting times.
Live tour guide
Private group available


  • Get around The Loop like a local: at street level, underground, or perhaps even on the famous elevated rails
  • Enjoy classic made-in-Chicago snacks like Chicago-style popcorn and homemade chocolate
  • Discover why Chicago’s art, food scene and architecture is one of a kind
  • Feel the energy and buzz in one of Chicago’s beautiful lakefront parks
  • Join a carbon neutral tour, organized and led by an eco-certified tour operator
Full description
Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago) before heading off into the bustling city. Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily to move about the city in a network of underground tunnels. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, make your way to another delicious destination. Along the way, enjoy views of the world-famous Wrigley Building and the incredible Chicago Tribune building, the heart of Chicago’s thriving and historic journalism industry. Your second tasty confection is locally made chocolate from a Chicago staple. Finally, take a stroll through the beautiful lakefront parks along Michigan Avenue. Round up your tour in the picturesque Millennium Park, home to the iconic Bean sculpture. Here, your guide will conclude your tour and point you in the right direction toward more amazing sights, great lunch spots, or drink recommendations.
  • English-speaking guide
  • Popcorn tasting
  • Chocolate tasting
  • Gratuities

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Meeting point

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

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Important information

What to bring

  • Comfortable shoes
  • Weather-appropriate clothing

Know before you go

  • This tour is organized and led by the world's largest travel B-Corp certified company. B-Corp Certification measures a company’s social and environmental impacts and responsible tourism practices
  • This tour runs year-round and will proceed rain or shine unless such weather constitutes a dangerous situation
  • In the event of road or attraction closures, your guide will do their best to work around the obstacles or take your tour to alternate locations
Customer reviews

Overall rating

4.8 /5

based on 38 reviews

Review summary

  • Guide
  • Value for money
  • Service
  • Organization

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We had a great time, our guide John was very knowledgeable and took the time to provide plenty of details and the background around the places we’ve seen during the tour. He was entertaining as well and very approachable. We’d definitely recommend this tour and John to other people interested in this type of tour.

March 25, 2023

ASK FOR LARA! Such a great tour! Our tour guide Lara was the best! She was funny, witty, spunky & her background as a teacher was the cherry on top! FOOD was delicious and FILLING! If for whatever supernatural reason you’re not full by the end of the tour I would recommend you to go see a doctor since you may have a second stomach you’re not aware of & this is coming from a foodie. We always had leftovers which was nice to see Lara give our extra food to those in need! We got to see so much! I recommend you bring comfy shoes for sure! We went at an easy pace and Lara always made sure we were good. Also bring some water since you do get thirsty! I wish I would have gone at the beginning of my trip and not towards the end of it. I would have had more time to appreciate all the details and history of beautiful Chicago! Thank you LARA!!!

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March 25, 2023

Kelly, our guide, was phenomenal! We live in the Chicagoland suburbs so thought to take an official tour to learn more details than the obvious ones we already knew. Kelly fulfilled that with much knowledge, grace and charm. Had a wonderful tour and learned a lot!!!

March 25, 2023

Product ID: 243062