Page 8 - Best Sightseeing 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: Evolution of the Skyscraper Walking Tour

8 Reviews

Chicago: Evolution of the Skyscraper Walking Tour

Chicago built some of the world’s first skyscrapers, with changing designs and technologies over time. Explore how these major developments came about, with examples from classic buildings to super-tall highrises from 1872 to the present.

$30.00

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Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

73 Reviews

Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

Learn about the stories of gangsters, politicians, and more in the spaces where it happened on a bus or walking tour. Visit the speakeasies that made the famous, infamous.

$47.70

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Chicago: Luxury City Minibus + Riverboat Architecture Tour

8 Reviews

Chicago: Luxury City Minibus + Riverboat Architecture Tour

Experience the best of Chicago by land and water on a combined city tour. See the Windy City's iconic landmarks on a bus tour before heading to the river for a boat cruise.

$99.00

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Chicago: Winter Loop Walking Tour (with indoor stops!)

Embark on an unforgettable journey as we explore the vibrant Loop district. Admire the towering skyscrapers and warm up inside some of the city's most breathtaking public buildings and lobbies.

$39.00

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Love is in the Windy City – Chicago Walking Tour

"Explore Chicago’s heart from Millennium Park’s Crown Fountain to Navy Pier, including iconic Cloud Gate and the innovative DuSable Bridge, in a journey through the city’s landmarks."

$597.77

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Chicago: Gangsters & Ghosts Minibus Tour + Riverboat Cruise

Discover Chicago's haunted past on a luxury Gangsters & Ghosts minibus tour, plus a Riverboat Architecture Cruise!

$99.00

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Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

83 Reviews

Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

Watch the fireworks dance over Chicago's skyline on this popular 1-hour speedboat tour. Enjoy panoramic views of a magnificent fireworks display from the waters of Lake Michigan.

$61.82

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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: 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: 45-Minute Family-Friendly Architecture River Cruise

1516 Reviews

Chicago: 45-Minute Family-Friendly Architecture River Cruise

Cruise down the Chicago River and see the city’s most spectacular landmarks on a boat cruise with live, family-friendly commentary and a full-service bar on board.

$28.00

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Chicago: Group Walking Tour

Discover the art and architecture of Chicago on a 2-hour walking tour. Learn the story behind the famous sculpture made by Picasso and why there is a flamingo in the middle of the city.

$20.86

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