Guided tour

Chicago: History, Culture and Architecture Walking Tour

Chicago: History, Culture and Architecture Walking Tour

Likely to sell out

From US$ 47 per person

Likely to sell out

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 to receive 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. Learn more
Duration 2.5 hours
Check availability to see starting times.
Live tour guide
Private or small groups 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.
  • Access to Chicago City Hall
  • Access to Chicago Riverwalk
  • Access to Chicago Pedway
  • Access to Millennium Park
  • Live tour guide
    Covid-19 precautions
    Safety measures in place
    • All areas that customers touch are frequently cleaned
    • You must keep social distance while in vehicles
    • The number of visitors is limited to reduce crowds

    Select participants and date



    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

    4.9 /5

    based on 32 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.

    June 26, 2022

    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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    June 2, 2022

    I had an amazing time on this tour! In my opinion, the walking tour allowed me to see so much more of the city, up close and from my own personal viewpoint. The tour guides were very friendly, funny, and knowledgeable. We were even given "Garrett's Popcorn" and "Fannie May Chocolate" as some sweet treats. I highly recommend this tour, and I'm so glad that I did it!!

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    September 22, 2021

    Product ID: 243062