Things to do in
Chicago Pedway

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Chicago Pedway: Our most recommended tours and activities

Chicago: Food, Architecture and History Tour

1. Chicago: Food, Architecture and History Tour

Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago). 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. 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 where you can sample locally made chocolate from a Chicago staple. Next, take a stroll through the beautiful lakefront parks along Michigan Avenue. End up in 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. Start your food tour with a well-known Chicago fare: the Chicago-style hot dog. Every Chicagoan has their own preference as to how the dog should be made, and you’ll get a chance to try your guides’ favorite version. 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 real Chicago institution. Your tour ends here, and your guide will be happy to direct you back to your accommodation or share tips for what else to see and do in the city.

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Chicago: History, Culture and Architecture Walking Tour

2. Chicago: History, Culture and Architecture Walking Tour

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.

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Other Sightseeing Options in Chicago Pedway

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What people are saying about Chicago Pedway

Overall rating

4.9 / 5

based on 36 reviews

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!!

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!!!

This was my first time to Chicago this tour was absolutely amazing. Kelly was knowledgeable about everything Chicago..she was able to answer all questions & gave great recommendations. Would highly recommend..

Small group, only 10 on our tour. Our guide was Kevin and he did a great job. Very fun and informational. I highly recommend a smaller group.

Very informative with a guide that guarantees you get a look into local favorites.