Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treat and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!
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The Chicago Theatre - Our tour kicks off beneath the iconic marquee of the Chicago Theatre, a familiar sight from numerous films and TV shows, before we venture into the lively city.
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Chicago Pedway - If the weather is favorable, we’ll make our way to the Chicago Pedway. This distinctive feature of the city is a network of underground tunnels used daily by locals and commuters, especially during the harsh Midwest winters.
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City of Chicago - City Hall - We’ll pass by the City Hall-County Building, commonly referred to as City Hall, which houses the government offices of both the City of Chicago and Cook County.
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Picasso Statue - Our next stop is the Chicago Picasso sculpture by Pablo Picasso in Daley Plaza. Installed in 1967, The Picasso marked a significant shift in civic and urban planning, expanding the concept of public art beyond mere commemoration.
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Chicago River - Feel like a local as you zip past buildings and take in more stunning views. If your guide opts for a water taxi, you’ll experience the Chicago skyline from a unique vantage point, sharing in the daily commute of Chicagoans.
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Chicago Riverwalk - This award-winning $150 million, 1.25-mile promenade along the south bank of the Chicago River downtown offers breathtaking views. Weather permitting, we’ll stroll along the Riverwalk, admiring several towering buildings like Marina Towers, the Wrigley Building, and the Chicago Tribune.
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Wrigley Building - We’ll pass the Wrigley Building, located on the Magnificent Mile directly across Michigan Avenue from the Tribune Tower. Its two elaborate towers, built between 1920 and 1924, originally housed the Wrigley Company’s corporate headquarters.
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Tribune Tower - We’ll pass by the Tribune Tower, a 463-foot-tall (141 m), 36-floor neo-Gothic skyscraper at 435 North Michigan Avenue.
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The Magnificent Mile - We’ll pass through the Magnificent Mile, a premier commercial district in downtown Chicago. Part of the 1909 Burnham Plan, this area was transformed in the 1920s from an industrial and residential zone into a bustling hub of shops, restaurants, hotels, and attractions on North Michigan Avenue.
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Chicago Cultural Center - Step inside this Chicago Landmark building, managed by the Department of Cultural Affairs. The Cultural Center serves as the city’s official reception venue, where the Mayor of Chicago has welcomed presidents, royalty, diplomats, and community leaders.
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Millennium Park - Next, we’ll visit the picturesque Millennium Park, home to the iconic Bean sculpture. Here or nearby, your guide will conclude the tour and provide recommendations for more sights, lunch spots, or drinks.
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Cloud Gate - We’ll pass by Cloud Gate, a public sculpture by Indian-born British artist Anish Kapoor, which serves as the centerpiece of AT&T Plaza at Millennium Park in the Loop community area.
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River North - Your food tour begins with a classic Chicago treat: the Chicago-style hot dog. Every local has their own preferred way to make it, and you’ll get to try your guide’s favorite version.
Next, indulge in the world-famous Chicago deep-dish pizza! This hearty dish, a staple of Chicago’s food scene, originated in River North in the 1940s to provide filling meals at low prices. Your guide will take you to a beloved local pizzeria to sample the authentic version.
After enjoying pizza and hot dogs, we’ll visit two more essential establishments in Chicago’s food culture. Our tasting journey continues with a classic Chicago sandwich: Italian beef. You’ll sample this sandwich at a true Chicago institution, complete with no-frills decor.
- Historic Water Tower - We’ll pass by the beautiful water tower, built in 1869 to house a large water pump drawing water from Lake Michigan. It is the second-oldest water tower in the United States.
- The Loop - Stroll through the main streets near the Loop, where you’ll find a unique blend of museums, restaurants, bars, historic landmarks, modern architecture, shops, and art galleries.
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- Transportation between tour halves
- Taste Chicago’s famous food like Chicago-style hot dog
- Try Deep dish pizza at an iconic Chicago pizza place
- Join professional English-speaking local guide
- Discover Chicago on 4 Food Stops with 4 Food Samples
- Get tips on what else to see, do and eat during your stay
- Discover Chicago’s incredible architecture both old and new
- Enjoy classic Chicago-style popcorn
- Taste a classic Chicago sandwich: Italian beef
- Gratuity
- Drinks and additional food
- This is a child-friendly walking tour. Children under the age of 6 are permitted to join this tour free of charge.
- Please note: food options and portion sizes will vary depending on the season and where we stop that day but the total amount of food included will be equal to a full meal.
- Suitable for all ages and fitness levels, but please note that this tour covers between 4.8 to 6.4 km (3-4 miles) of walking.
- 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.
- Experiences happen rain, shine, or snow. Please dress accordingly.
For a full refund, cancel at least 24 hours before the scheduled departure time.