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Chicago Guided City Tours

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Our Chicago Guided City Tours make for truly unique gifts they're sure to remember forever.

Cloud 9 Living's experience gifts are the perfect solution for anyone on your list and are guaranteed to bring a smile to your gift recipient's face.

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Walking Food Tour of Chicago
Walking Food Tour of Chicago
Avg. Rating of 4-half
(65 Reviews)

Enjoy this unique food tasting and cultural walking tour through Chicago's most delicious and historic neighborhoods.
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Region: Chicago
From: $50
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Downtown Chicago Kayak Tour
Architectural Kayak Tour
Avg. Rating of 5
(12 Reviews)

Explore the unique and intriguing past of Chicago's historic buildings from the seat of a kayak as you paddle the famous Chicago River.
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Region: Chicago
From: $76
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Chicago Lakefront Bike Tour
Chicago Lakefront Bike Tour
Avg. Rating of 5
(3 Reviews)

Take in Chicago's unique culture while getting a little exercise on this informative and relaxing bike tour.
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Region: Chicago
From: $49
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Hot Dog on Food Tour in Chicago
Bucktown & Wicker Park Food Tour
Avg. Rating of 5
(27 Reviews)

Enjoy this guided food tour of Bucktown & Wicker Park, two of Chicago's trendier neighborhoods which are home to some of the city's best restaurants and eateries.
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Region: Chicago
From: $50
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Deep Dish Pizza in Chicago
Chicago Pizza Tour
Avg. Rating of 4-half
(14 Reviews)

Come see the beautiful city of Chicago "One Slice at a Time" with this fun and delicious Chicago Pizza Tour!
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Region: Chicago
From: $60
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Chicago Prohibition Tour
Chicago Prohibition Tour
Avg. Rating of 4-half
(4 Reviews)

Plunge into one of the most defining moments in American history as you sip your way through the Chicago Prohibition Tour!
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Region: Chicago
From: $45
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Chicago Bike, Food and Beer Tour
Bikes, Bites, and Brews Tour
Avg. Rating of 5
(7 Reviews)

Enjoy Chicago's famous food, historic architecture and great beer on this Bikes, Bites and Brews tour.
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Region: Chicago
From: $79
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Chinatown Food Tour in Chicago
Chinatown Food Tour
Avg. Rating of 4-half
(14 Reviews)

Enjoy this unique food tasting and cultural walking tour through Chicago's remarkable Chinatown neighborhood.
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Region: Chicago
From: $60
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River North Food Tour in Chicago, IL
River North Food Tour

Experience the history, architecture and culture of River North while tasting delicious food on this River North Food Tour!
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Region: Chicago
From: $55
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Chicago Pizza & Cocktails Tour
Pizza & Cocktails Tour
Avg. Rating of 4-half
(3 Reviews)

A slice of classic Chicago style pizza isn't quite the same without a tasty adult beverage to go with it. Combine the best of both worlds with the Pizza & Cocktail Tour of Chicago!
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Region: Chicago
From: $80
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From: $50
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Chicago's Best Food Tour
Best of Chicago Food Tour

Chicago boasts nearly 7,000 restaurants within its city limits. Sit back, relax, and taste the best of the best with this Best of Chicago Food Tour!
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Region: Chicago
From: $105
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South Side Food Tour in Chicago
South Side Culinary Tour

Disover the rich history of Chicago's up-and-coming South Side while indulging in some of the best food in town!
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Region: Chicago
From: $132
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Pilsen Food Tour in Chicago
Pilsen Food and Culture Tour

Explore the unique and mouthwatering cuisine of Chicago's Pilsen neighborhood while learning about the rich and vibrant history of this up and coming area.
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Region: Chicago
From: $132
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Little Arabia Food Tour in Chicago
Little Arabia Food Tour
Avg. Rating of 4-half
(2 Reviews)

Discover a mecca of food in Albany Park and along Kedzie Avenue on the Little Arabia Food Tour!
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Region: Chicago
From: $60
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Indian Food & Cultural Walking Tour in Chicago
Little India Food & Culture Walking Tour
Avg. Rating of 5
(2 Reviews)

Embark on a one of a kind culinary and cultural tour through Chicago's "Little India"!
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Region: Chicago
From: $75
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Fireworks Bike Tour in Chicago
Fireworks Bike Tour
Avg. Rating of 5
(2 Reviews)

Culture yourself while getting a little exercise on this fun and relaxing evening bike tour of Chicago!
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Region: Chicago
From: $49
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Fireworks Kayak Tour in Chicago
Fireworks Kayak Tour
Avg. Rating of 4-half
(8 Reviews)

Kayak at night, through the city and down the Chicago River to watch a brilliant fireworks display from the cockpit of a kayak.
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Region: Chicago
From: $76
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Al Capone South Side Tour
South Side Gangster Bike Tour
Avg. Rating of 5
(1 Reviews)

Discover the historic, scenic and seedier side of Chicago on the South Side Gangster Bike Tour!
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Region: Chicago
From: $61
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Chicago Sunset Bike Tour
Chicago Sunset Bike Tour

Watch the sun dip behind one of the world's most spectacular city skylines on the Chicago Sunset Bike Tour!
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Region: Chicago
From: $43
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Downtown Segway Tour in Chicago
Downtown Chicago Segway Tour
Avg. Rating of 5
(6 Reviews)

Cruise through the beautiful parks and sidewalks of Chicago as your guide entertains you with fascinating stories, great photo ops and little known facts of the area!
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Region: Chicago
From: $70
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Evening Segway Tour in Chicago
Fireworks Segway Tour

Take in some of the city's favorite landmarks and watch a magnificent fireworks display on the Fireworks Segway Tour in Chicago!
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Region: Chicago
From: $70
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From pizza to pedaling, culture to cocktails, fireworks, and so much more — experience the sheer delight of Chicago guided city tours!

There are countless things to do in Chicago. Among this infinite list are the city's food tours, featuring an array of ways to eat, drink and be merry. Enjoy an all-encompassing experience of the Windy City's most mouthwatering cuisine, fascinating histories, unique districts, rich entertainment and more — the Walking Food Tour of Chicago is a must-do for locals and visitors alike! Explore the sights and sounds of the city's most diverse neighborhoods.

Indulge in tastes of classic, Chi-town style pies, accompanied by refreshing libations on the Chicago Pizza and Cocktails Tour! Or wander through culture-infused streets on food tours that blend Chicago sightseeing with the authentic eats of renowned areas like Little India, Chinatown, Little Arabia, Bucktown and Wicker Park.

Give a hearty "Cheers!" to Chi-town while diving into the riveting stories of spirits' past on the Prohibition Cocktail Tour. Engage in one of America's most intriguing blasts from the past, featuring people and places to see in Chicago that shaped this famous dry era. Take a stroll down memory lane, while sipping on forbidden fruits of the 20s and 30s!

Maybe you prefer to move 'n' groove your way along Chicago guided city tours? You've come to the right place! Check out the very best things to see in Chicago with Cloud 9 Living's unique collection of ways to get around that go beyond walking.

Hop on a bike and pedal your way to famous Chicago attractions! Coast by the scenic Lakefront, enjoying the fresh air of Lake Michigan and the awe-inspiring views of the skyline. Check out the city's skyscrapers in the warm glow of sunset. Roll along the South Side turf for an up-close and personal exploration of the homes, hideouts and hot spots of renowned mobsters like Al Capone. Or take sightseeing in Chicago by storm on the ever-popular Bikes, Bites, and Brews Tour; indulge in the most tempting local eats and treats while cycling through areas like Wrigleyville, Gold Coast, Old Town, and Lincoln Park.

Want to put a super-unique twist on Chicago guided city tours? Check out urban architecture, evening fireworks, and downtown landmarks like Navy Pier, The Field Museum, Millennium Park, Soldier Field, and much more by either kayak or Segway!