Must-See in Chicago: Architecture, History & Culture Tour

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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.


  • Get around The Loop like local: at street level, underground,...
  • Enjoy classic Chicago snacks like Chicago-style popcorn and 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 parks
  • Choose between a shared group or private tour


Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago) and 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 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. Along the way, enjoy views of the world-famous Wrigley Building and the incredible Chicago Tribune building. Your second tasty confection is locally made chocolate from a Chicago staple. 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.


Local English-speaking guide Popcorn tasting Chocolate tasting

Important Information

  • This tour is carbon neutral, operated by a B Corp certified company committed to using travel as a force for good. This Certification measures a company’s social and environmental impacts and responsible tourism practices.
  • The maximum number of people on small group tour will be 16 passengers.
  • This is a child-friendly walking tour. Children under the age of 6 are permitted to join this tour free of charge.
  • Suitable for all ages and fitness levels, but please note that this tour covers about 4.8 km (3 miles) of walking.
  • Experiences happen rain, shine, or snow. Please dress accordingly.
  • 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.

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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