Chicago Walking Tours

Chicago Walking Tours

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For authentic cuisine with a rich history, embark on a Chinatown food and walking tour with Bobby’s Bike Hike, America’s longest running city bike tour company. As you stroll through Chinatown’s neighborhoods on this 2.5-hour tour, you’ll sample Cantonese dim sum and tea, try Portuguese-Chinese baked goods, and so much more. Plus, you’ll learn about the history behind the cuisine and culture. Details
TripAdvisor user rating 5.00 out of 5
3176 Reviews
$63.21
Get ready to sample Chicago’s iconic food, including deep dish pizza, the original chocolate brownie, and local craft beers. This walking tour brings you around to some of the most renowned restaurants and bars in the city. Along the way, you’ll come across Chicago’s landmarks, well-known neighborhoods, and historic spots. This tour is not recommended for kids under the age of 17. Details
TripAdvisor user rating 5.00 out of 5
3176 Reviews
$63.21
Presented by Chicago Detours, 1893 World’s Fair Tour with Bars and Food offers a three-hour experience that’s broken up into 95% indoors and 5% outdoors. Tour highlights include seeing the grand lobby of the Auditorium Building, tasting mouth watering German food at the Berghoff Restaurant, a secret alley building, one of the last elevators with a human operator in downtown Chicago and more. Details
TripAdvisor user rating 5.00 out of 5
597 Reviews
$49.00 $42.00
You Save: $7.00
Operated by Bobby’s Bike Hike, this comedy walking tour will make your sides hurt from so much laughing! Spend 2.5 hours exploring Chicago’s Old Town neighborhood where you’ll visit a comedy club, sample local craft beer, and learn more about the area’s history. Due to the nature of this tour, only guests ages 21 and up are permitted to participate. Details
TripAdvisor user rating 5.00 out of 5
3176 Reviews
$67.75
Presented by Chicago Detours, the Best Architecture Walking Tour Since Sliced Bread is a 1.5-hour experience for guests of all ages to enjoy. The tour showcases architecture, graphic design, fashion design and pop culture, while learning about how they connect with Chicago’s history. Highlights include Michigan Avenue Bridge, Jeanne Gang’s famous Aqua Tower, Chicago’s underground layers and more. Details
TripAdvisor user rating 5.00 out of 5
597 Reviews
$25.00
Presented by Chicago Detours, Historic Chicago Walking Bar Tour offers a 2.5-hour experience sampling some of the area’s best eats and drinks, seeing the beautiful architecture and learning about its history from the Prohibition era. Highlights include Tribune Tower, the famous Billy Goat Tavern, a 19th-century mansion, a former historic jazz club and speakeasy, Magnificent Mile and more. Details
TripAdvisor user rating 5.00 out of 5
597 Reviews
$36.00
There’s nothing more magical than Chicago during the holiday season. Embark on a walking tour through Chicago’s most festive neighborhoods and restaurants. Sample the city’s best pizza while marveling at sights and decorations along the Magnificent Mile, strolling through Christkindlmarket, and sipping on the Windy City’s best craft beer. It’ll be a holiday season unlike any other! Details
TripAdvisor user rating 5.00 out of 5
3176 Reviews
$67.75
Presented by Chicago Detours, Loop Interior Architecture Walking Tour offers a unique way to get an in-depth view of downtown Chicago’s beautiful architecture. Guests will see inside a variety of lobbies, corridors, the underground Pedway system and more, with roughly 95% of the tour taking place indoors. Highlights include the “Chicago Picasso” sculpture, Chicago Cultural Center and more. Details
TripAdvisor user rating 5.00 out of 5
597 Reviews
$28.00