Chicago Guided City Tours
- See All 67 Experiences
- Action & Adventure
- City Tours
- Food & Wine
- Life & Culture
- Spa Packages
- Water Activities
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.
Create a memory. Give the gift of experience!
Enjoy this unique food tasting and cultural walking tour through Chicago's most delicious and historic neighborhoods.
More Details and video
Explore the unique and intriguing past of Chicago's historic buildings from the seat of a kayak as you paddle the famous Chicago River.
Take in Chicago's unique culture while getting a little exercise on this informative and relaxing bike tour.
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.
Come see the beautiful city of Chicago "One Slice at a Time" with this fun and delicious Chicago Pizza Tour!
Plunge into one of the most defining moments in American history as you sip your way through the Chicago Prohibition Tour!
Enjoy Chicago's famous food, historic architecture and great beer on this Bikes, Bites and Brews tour.
Enjoy this unique food tasting and cultural walking tour through Chicago's remarkable Chinatown neighborhood.
Experience the history, architecture and culture of River North while tasting delicious food on this River North Food Tour!
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!
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!
Disover the rich history of Chicago's up-and-coming South Side while indulging in some of the best food in town!
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.
Discover a mecca of food in Albany Park and along Kedzie Avenue on the Little Arabia Food Tour!
Embark on a one of a kind culinary and cultural tour through Chicago's "Little India"!
Culture yourself while getting a little exercise on this fun and relaxing evening bike tour of Chicago!
Kayak at night, through the city and down the Chicago River to watch a brilliant fireworks display from the cockpit of a kayak.
Discover the historic, scenic and seedier side of Chicago on the South Side Gangster Bike Tour!
Watch the sun dip behind one of the world's most spectacular city skylines on the Chicago Sunset Bike Tour!
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!
Take in some of the city's favorite landmarks and watch a magnificent fireworks display on the Fireworks Segway Tour in Chicago!
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!