Guided tour

Chicago: Food, History and Architecture Tour with Tastings

4.8 / 5

17 reviews

Chicago: Food, History and Architecture Tour with Tastings

Likely to sell out
Likely to sell out

From US$ 99 per person

Get an extensive overview of Chicago's history, beautiful architecture, and delicious food on a guided day tour through the city.

About this activity

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Covid-19 precautions
Special health and safety measures apply. Learn more
Reserve now & pay later
Reserve now & pay later to book your spot without any charges today. Learn more
Duration 5 hours
Check availability to see starting times.
Live tour guide
Small group
Limited to 9 participants


  • Marvel at the stunning architecture of the Chicago skyline
  • Feel like a local as you ride public transportation and try Chicago classics
  • Enjoy food samples such as Chicago-style hot dog, pizza and Italian beef
  • Get a taste for the city's most famous food in a historic neighborhood
  • Join a carbon neutral tour, organized and led by an eco-certified tour operator
Full description

Discover the best of Chicago on a comprehensive guided tour. Learn more about the city's history and vibrant food scene as you discover various bustling neighborhoods and historic areas.

Start your tour under the dazzling marquee of the Chicago Theater, recognizable from movie-musical Chicago before heading off into the bustling city. First, stop at the Chicago Pedway, used by locals and commuters daily to move about the city in a network of underground tunnels.

From here, head towards the official seat of the government for the city at City Hall. Check out its classic interior design and architecture. 

Next, enjoy your first food tasting of the day, traditional Chicago-style popcorn. Weather permitting, your guide will take you for a stroll along the Chicago Riverwalk, pointing out familiar buildings such as the Marina Towers, the Britannica Building, and the Willis Tower.

From here, make your way to another delicious destination where you can sample locally made chocolate from a local shop. 

Then, you will either hop on the ‘L’ train or a water taxi on the Chicago River, depending on the weather and time of year. Either option offers a uniquely local Chicago experience. Feel like a local as you zip past buildings and catch even more awesome views.

Next, take a stroll through the beautiful lakefront parks along Michigan Avenue. Arrive at the picturesque Millennium Park, home to the iconic Bean sculpture. By then, you’ll hopefully have built up an appetite because it’s time to begin your ultimate food experience.

Travel with your guide up to the River North neighborhood, the original Chicago foodie destination. Your first food sampling is a local favorite, a Chicago-style hot dog.

Next up is the world-famous Chicago deep-dish pizza, the staple of the Chicago food scene. Visit a pizza place that’s an icon to Chicago natives to try the real deal for yourself. After you’ve filled up on pizza and hot dogs, take a stroll through two more establishments, each one essential to Chicago’s food culture.

Then continue your tasting journey with a classic Chicago sandwich: Italian beef. Sample this sandwich in a true Chicago institution. Your tour ends here, but don’t forget to get some recommendations from your guide of where else you visit or eat during tour time in the city.

  • Access to Chicago Riverwalk
  • Access to Millennium Park
  • Access to Chicago Pedway
  • Live tour guide
  • Pizza
  • Sandwich
    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
    Traveler requirements
    • You are required to bring and wear a mask

    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
    Customer reviews

    Overall rating

    4.8 /5

    based on 17 reviews

    Review summary

    • Guide
    • Value for money
    • Service
    • Organization

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    Star rating:

    our guid Wallach was amazing, every question we asked him he knew the answer for, was able to customize our tour on the fly for us when we expressed interest in things he did not originally plan on covering. and even whent so far as to end the tour hotell. then gave us the locations of several other places and restaurants we should try while we were in town.

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    April 17, 2021

    My guide showed good knowledge of Chicago. He seemed very personable as well. Probably too much food at the end. As glad as I was to get a taste of the Chicago classics, the three stops were overkill. Plus, stopping for chocolate at Fannie May? Seriously, I can get that anywhere. Not a treat specific to Chicago at all.

    April 1, 2021

    Our tour Guide was so friendly. He was knowledgeable and fun. The only thing I would add is to have a speaker for him to talk through for people in the back. With mask and construction it made his great information hard to hear. I would definitely recommend this tour to my family and friends.

    March 19, 2021

    Product ID: 243137