Page 9 - Best Experiences in Chicago

Local Recommendations from our My Guide Chicago team

Book Top Experiences and Tours in Chicago:

If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!

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Chicago: Downtown Donut Tour with Tastings

89 Reviews

Chicago: Downtown Donut Tour with Tastings

Take a trip with Chicago's only donut tour. Making 4 stops at some of the city's best donut shops, you'll sample all the best donuts Chicago has to offer. Enjoy samples at each location and learn about the history of donuts in the windy city.

$68.00

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Chicago: Lake Michigan Skyline Cruise

700 Reviews

Chicago: Lake Michigan Skyline Cruise

See the sights of Chicago from Lake Michigan on this sightseeing lake cruise. Admire stunning views of the Chicago skyline and see many of the city’s iconic landmarks.

$37.57

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Chicago: Art Institute Skip-the-Line Tour with Guide

30 Reviews

Chicago: Art Institute Skip-the-Line Tour with Guide

Experience some of the world's most famous pieces of art on a guided tour of the Art Institute of Chicago. Explore great art, before the doors even open to the general public.

$132.50

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Chicago: Ghosts & Haunted History Walking Tour

1 Reviews

Chicago: Ghosts & Haunted History Walking Tour

Walk with us as the sun sets through downtown Chicago hearing some of the most gruesome and creepy Chicago stories. Expect more history and humor than hauntings.

$29.00

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Chicago: 1.5-Hour Scenic Sunset Lake Cruise

633 Reviews

Chicago: 1.5-Hour Scenic Sunset Lake Cruise

Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise. Toast the end of the day with a glass of wine, ice-cold beer or hand-crafted cocktail.

$45.00

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Chicago: American Writers Museum Flexible Date Entry Ticket

97 Reviews

Chicago: American Writers Museum Flexible Date Entry Ticket

Explore over 400 years of American writing of all genres with this entry ticket to the American Writers Museum. Benefit from a flexible entry date and see the interactive Nation of Writers Gallery.

$0.00

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Chicago: Milwaukee Harley-Davidson Museum & Brewery Day Tour

3 Reviews

Chicago: Milwaukee Harley-Davidson Museum & Brewery Day Tour

Discover the mechanics behind how motorcycles work and learn about the iconic history of Harley-Davidson through a gallery of bikes from 1903 to the present.

$125.00

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Chicago's Original Dazzling Architectural Interiors Tour

26 Reviews

Chicago's Original Dazzling Architectural Interiors Tour

Explore fascinating interior spaces in downtown Chicago with an expert guide.

$35.00

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Travel between Chicago O'Hare and Madison

4 Reviews

Travel between Chicago O'Hare and Madison

Discover Madison with easy transfer from/to Chicago O'Hare Airport on modern buses operated by Coach USA

$38.10

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Amazing Lakefront Segway Tour of Chicago

109 Reviews

Amazing Lakefront Segway Tour of Chicago

Glide around the Chicago lakefront on a Segway tour. Zip past the cascading fountains of Millenium Park, admire the city's towering skyline, and swoop through Grant Park’s manicured gardens.

$65.00

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Chicago: Westside Food Tasting Bike Tour with Guide

16 Reviews

Chicago: Westside Food Tasting Bike Tour with Guide

Eat around the world without leaving Chicago! Enjoy the city's best ethnic cuisines while biking through its most historic neighborhoods and along the gorgeous 606 and Lakefront trails.

$89.99

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