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11 results
Best Seller
Sample some of the Windy City's tastiest donuts—and head to locals-loved dessert destinations that most visitors miss—on this one-of-a-kind walking tour. With your guide in the lead, head to a number of Chicago’s tastiest donut bakeries, all while exploring the city's vibrant downtown Loop neighborhood. All tastings are included in the tour cost, and vegan, gluten-, and nut-free options are also available upon request.
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4.9
(1,415)
Delicious Donuts & City Sights: Chicago's Original Donut Tour
2 hours
Free Cancellation
from
$70
Head to one of Chicago’s top neighborhoods for food lovers—and try donuts from four of the Windy City’s top specialty bakeries—on this indulgent walking tour. Meet your guide at the Chicago French Market in the morning, and come hungry: you’ll enjoy four different donuts, each representing different culinary styles and traditions. As you go, wander the West Loop and Restaurant Row, and learn more about Chicago’s dining scene.
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5.0
(61)
Delicious Donuts & Sweet Treats: West Loop Walking Tour
1 hour 30 minutes to 2 hours
Free Cancellation
from
$70
Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.
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4.8
(16,018)
Chicago Architecture River Cruise
1 hour to 1 hour 30 minutes
Free Cancellation
from
$39
Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.
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4.9
(1,220)
Chicago in a Day: Food, History & Architecture Walking Tour
4 hours 30 minutes
Free Cancellation
from
$101
Price varies by group size
Delve into Chicago’s one-of-a-kind cuisine and learn something that you would never expect on this small-group Secret Food Tour. Eat your way through the most prominent neighborhoods of the city and immerse yourself in its tastes and flavors. Stroll through the Loop and Millenium Park, wander down the Riverwalk and discover iconic sights and hidden gems from another perspective. Get inside Chicago’s life through food and connect your heart and soul to the Windy City vibe while tasting classic deep-dish pizza, dipped Italian beef, and Chicago-style hot-dogs. • Benefit from small-group experience and undivided attention from your local guide • Savor the classic Chicago eats and get to know the history of their creation • Witness fascinating art objects, architecture landmarks, and beautiful cityscapes • Get useful recommendation of where to eat and drink from your guide
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5.0
(4)
Chicago Foods Tour with The Loop, Skyline, Millennium Park
3 hours
Free Cancellation
from
$145
Special Offer
Explore a new side of Chicago and the city's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, John Dillinger, and more famous figures hung out. There are ample chances to get out of the bus and pose for pictures in front of a historic courthouse, among other infamous sites.
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4.6
(3,300)
Chicago Crime and Mob Bus Tour
1 hour 30 minutes to 2 hours
Free Cancellation
from
$42
$49
Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.
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4.9
(2,058)
Chicago Favorites Ultimate Food and Walking Tour
3 hours
Free Cancellation
from
$85
Likely to Sell Out
Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and combine it with tasting the most delicious and iconic treats of the Chi after whetting your appetite, absorbing the unique beauty of the city. Discover more sights in a shorter time using a bike Get a true taste of the City by the Lake following the tips of a local guide Discover iconic neighborhoods and be entertained with historical insights. Learn about the peculiarities of local cuisine and its origins.
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Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer
4 hours
Free Cancellation
from
$179
Immerse yourself in Chicago's thriving craft beer scene—and visit locals-loved breweries you'd be unlikely to stumble across otherwise—on this half-day brewery tour. Travel in style, and get in the spirit, aboard a traditional Prohibition–style barrel bus. Visit several unique breweries, and go on behind-the-scenes production facility tours. Discover the science behind the brewing process, and enjoy plenty of beer samples throughout the tour.
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4.9
(348)
Chicago Craft Brewery Barrel Bus Tour
3 hours 45 minutes
Free Cancellation
from
$100
Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.
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4.9
(735)
Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults
4 hours 30 minutes
Free Cancellation
from
$89
Explore downtown Chicago through the lens of movies and TV on this walking tour that takes you to the filming locations for *Ferris Bueller’s Day Off*, *The Untouchables*, *The Dark Knight*, *The Bear*, *the Blues Brothers*, and more. Along the way, your local actor-guide shares behind-the-scenes stories, trivia, and fun facts you won’t get from walking the city on your own.
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4.3
(24)
Downtown Chicago TV and Movie Sites Guided Walking Tour
2 hours
Free Cancellation
from
$44
Top Attractions in Chicago
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Attractions
The Magnificent Mile
From $12
Attractions
Chicago Theatre
From $12
Attractions
Skydeck Chicago at Willis Tower (Sears Tower)
From $12
Attractions
Chicago River
From $28
Attractions
Chicago Riverwalk
From $12
Attractions
Art Institute of Chicago
From $12
Attractions
The Magnificent Mile
From $12
Attractions
Chicago Theatre
From $12
Attractions
Skydeck Chicago at Willis Tower (Sears Tower)
From $12
Attractions
Chicago River
From $28
Attractions
Chicago Riverwalk
From $12
Attractions
Art Institute of Chicago
From $12
Attractions
The Magnificent Mile
From $12
Attractions
Chicago Theatre
From $12
Attractions
Skydeck Chicago at Willis Tower (Sears Tower)
From $12
Attractions
Chicago River
From $28
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