Page 2 - Best Sightseeing Tours 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: Fireworks Cruise with Lake or River Viewing Options

252 Reviews

Chicago: Fireworks Cruise with Lake or River Viewing Options

Get up-close and personal to the epic Navy Pier fireworks display every Wednesday & Saturday during the Summer. Choose between viewing from either the Chicago River or Lake Michigan.

$28.00

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Chicago: Guided Tour with Skydeck and Shoreline River Cruise

20 Reviews

Chicago: Guided Tour with Skydeck and Shoreline River Cruise

See the best of Chicago in just 1 day on this guided sightseeing bus tour. Visit iconic landmarks including Chicago Skydeck, the Bean, and Adler Point, and learn about Chicago’s history and culture.

$254.00

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Chicago River: Guided Sunset Cocktail & Architecture Tour

53 Reviews

Chicago River: Guided Sunset Cocktail & Architecture Tour

Climb aboard a 90 passenger historic riverboat & sip cocktails while cruising the Chicago River! Relax and learn about the history & architecture of the city via live narration with a drink in hand.

$59.00

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Chicago: Architecture River Cruise Skip-the-Ticket Line

3894 Reviews

Chicago: Architecture River Cruise Skip-the-Ticket Line

Cruise along the Chicago River on a boat tour and discover hidden architectural gems among the city’s renowned landmarks, with live narration.

$53.00

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Chicago: The Curious Curse of the Chicago Cubs Audio Tour

Take a fictional, self-guided audio tour exploring the mysterious curse of the Chicago Cubs. Experience the magic of GPS-playback on this immersive stroll.

$4.99

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Chicago: Full Day Food Walking Tour + FREE Bike/Kayak Rental

2 Reviews

Chicago: Full Day Food Walking Tour + FREE Bike/Kayak Rental

Make the most of your day in Chicago by sampling Chicago's iconic style foods, seeing top attractions with a local, expert guide. Includes a FREE 2 hr bike or kayak rental to explore even more.

$99.99

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Chicago Walking Tour: See Inside Art Deco Masterpieces

1 Reviews

Chicago Walking Tour: See Inside Art Deco Masterpieces

Experience the elegance, glam, and glitz of the 1920s on this 2-hour walking tour of downtown Chicago! Most tours walk right by these stunning masterpieces without ever going inside -- but we do!

$35.00

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Chicago TV & Movie Locations Walking Tour

Whether you’re a movie fanatic or simply want to take a Chicago sightseeing tour that hits iconic landmarks, this private walking tour is for you!

$320.00

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Chicago’s Festive Lights: A Magical Christmas Journey

"Experience the holiday magic in “Chicago’s Festive Lights”, starting at 875 North Michigan Avenue, through N State St, and ending at Christkindlmarket for a traditional Christmas celebration."

$679.64

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Chicago: Downtown Donut Tour with Tastings

86 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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Route 66 Self-Guided Drive from Chicago to St Louis

1 Reviews

Route 66 Self-Guided Drive from Chicago to St Louis

Embark on a self-guided road trip from Chicago to Springfield. Drive along the historic Route 66, explore the Route 66 Hall of Fame and Museum, and visit the Illinois State Capitol.

$4.34

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