Guided tours in Chicago

Walking, bike and themed tours of the city itself.

For the operators we researched and recommend, see our food tours and cooking classes in Chicago, or the experiences overview.

Guided tours

Chicago Architecture, History and Culture: Loop Walking Tour

Guided tour3 hours5.0 from 3 reviewsfrom $50

This architecture and history tour gives an introduction into what defines Chicago. We'll walk the streets of the Loop, see beautiful interiors and, of course, get to ...

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Chicago: The Devil In The White City Bus Tour

Guided tour3 hours4.5 from 2 reviewsfrom $64

Dive into the dark history of Chicago with The Devil In The White City Bus Tour. Explore sites from Erik Larson’s bestselling book, including the infamous Murder Castl...

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Chicago: Full-Day Guided City Tour by Bus

Guided tour1 dayfrom $128

Discover the best of Chicago on a full-day city tour with a local guide. See the city's top sights, including Millennium Park and Michigan Avenue, and customize your e...

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From Chicago: 1-Hour Nature Horseback Ride

Guided tour1 hour4.0 from 2 reviewsfrom $138

Escape the city for a relaxing horseback ride through peaceful natural landscapes near Starved Rock State Park, with convenient transportation from Chicago.

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Chicago in Spanish. Architecture. Mafia, Secrets. Interiors, Underground

Guided tour3 hours5.0 from 2 reviewsfrom $45

At 10:30 AM, the Chicago that few know begins. Be amazed by experts who turn monuments into stories, secrets into souvenirs, and a tour into an unforgettable experience.

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Chicago: University of Chicago Student-Led Campus Tour

Guided tour2 hoursfrom $160

Explore the University of Chicago on a student-led tour. Discover the campus’s unique blend of Collegiate Gothic and modern architecture and learn about its rich history.

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Chicago: Prairie Avenue Ghost Hunt

Guided tour2 hoursfrom $38

Dive into the haunted history of Chicago's Millionaire's Row with the Prairie Avenue Ghost Hunt. Encounter the spirits of Gilded Age magnates like Marshall Field and G...

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The Chicago Theatre Tour Experience

Guided tour1 hour4.7 from 167 reviewsfrom $32

Unlock the secrets of Chicago's most-photographed venue with The Chicago Theatre Tour Experience. Marvel at the grandiose architecture and walk in the footsteps of leg...

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Downtown Chicago TV & Movie Filming Locations Walking Tour

Guided tour2 hours4.8 from 24 reviewsfrom $43

From Ferris Bueller’s Day Off to The Untouchables to The Dark Knight, enjoy a fascinating walking tour to over 30 film locations in Chicago. Learn unique behind-the-sc...

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Chicago: Art Institute Skip-the-Line Guided Tour 12ppl Max

Guided tour2.5 hours5.0 from 58 reviewsfrom $90

Experience some of the world's most famous pieces of art on a guided tour of the Art Institute of Chicago. Explore great art, before the doors even open to the general public.

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Chicago Amazing Lakefront Bike Tour

Guided tour2 hours4.2 from 15 reviewsfrom $49

Chicago's lakefront is a biking paradise! Join us for a fun, casual ride and urban safari. Our route includes it all: beaches, lagoons, gardens, animals, architecture ...

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Chicago: Underground Pedway & Downtown Secrets Walking Tour

Guided tour2 hours4.8 from 316 reviewsfrom $28

Explore downtown Chicago through its underground passageways, known as "The Pedway," accessing beautiful interiors from both above ground and below, with secrets along...

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Chicago: Secret Interiors Architecture Walking Tour

Guided tour2 hours4.8 from 658 reviewsfrom $31

Discover the hidden interiors of Chicago's most iconic buildings on a guided architecture tour. Explore the Rookery, Chicago Cultural Center, Marquette Building, and C...

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Chicago: Art of a City, Downtown Chicago Guided Walking Tour

Guided tour2.5 hours5.0 from 2 reviewsfrom $55

Chicago's iconic art, architecture, and history await! Walk with our expert guide through the city’s streets, discovering masterpieces and uncovering the rich stories ...

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Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

Guided tour3 - 4 hours4.9 from 196 reviewsfrom $48

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.

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Chicago in a Day: Food, History & Architecture Walking Tour

Guided tour4.5 hours4.9 from 151 reviewsfrom $99

Discover the architecture and food scene of Chicago on a guided walking tour. Learn more about the prohibition era, explore the city's vibrant food scene, and taste so...

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Chicago's Best First Walk: Millennium Park & River Stories

Guided tour2 hours4.5 from 2 reviewsfrom $50

Explore how an abandoned industrial area transformed into the world's most renowned city park. Through vivid stories, experience the transformation process of Chicago.

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Chicago Walking Tour: See Inside Art Deco Masterpieces

Guided tour2 hours4.9 from 10 reviewsfrom $35

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 eve...

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Chicago: Sunset Tour by Open-top Bus with Live Guide

Guided tour1.5 hours4.6 from 92 reviewsfrom $39

Experience the Windy City’s dazzling skyscrapers and skyline with a sunset tour on an open-top double-decker bus. See Chicago from downtown to Museum Campus to Millenn...

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Walkin' with Colin: Chicago Tour du Jour

Guided tour2 hours5.0 from 8 reviewsfrom $44

Walkin'W/Colin is a one of a kind feet on the street experience recommended by 100% of travelers on Trip Advisor! Chicago History-Mystery-Comedy-Tragedy on a tour du j...

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Chicago Architecture & True Crime History Tour

Guided tour2 hours4.9 from 56 reviewsfrom $35

Interested in an architecture tour or a true crime tour during your stay? Get the best of both worlds with an expert guide who brings Chicago’s skyscrapers and its ser...

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Chicago: Art Institute Small Group Tour with Early Access

Guided tour2 hours2.9 from 6 reviewsfrom $90

Enjoy exclusive early access to the Art Institute of Chicago on a small-group guided tour. Explore Impressionist, American & Modern galleries and uncover the stories b...

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Chicago: Architecture Boat Tour with Drinks

Guided tour1.5 hours4.8 from 579 reviewsfrom $42

Experience the iconic scenery, skyscrapers, and architecture of Chicago on a guided boat cruise through the heart of the city. Pass by the Willis Tower, Wrigley Buildi...

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Amazing Lakefront Segway Tour of Chicago

Guided tour1.5 hours4.5 from 148 reviewsfrom $65

Glide around the Chicago lakefront on a Segway tour. Zip past the cascading fountains of Millenium Park, admire the city's towering skyline, and swoop through Grant Pa...

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Chicago: Ghost Bus Tour of Haunted Locations

Guided tour3 hours4.5 from 8 reviewsfrom $54

Join a ghost tour of Chicago established by author and seasoned paranormal researcher Ursula Bielski. Take the bus to intriguing sites, including the Lincoln Park Zoo,...

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Chicago Crimes Night Tour

Guided tour2 hours4.6 from 98 reviewsfrom $55

Explore Chicago's criminal history on a 2 - 2.5 hour night time tour. Discover the history of Chicago’s most famous criminals, gangsters and mobsters, such as the famo...

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Chicago's ORIGINAL Dazzling Architectural Interiors Tour

Guided tour2 hours4.9 from 54 reviewsfrom $28

Chicago's ORIGINAL (and recently copied) architecture interiors tour, with exclusive access to downtown Chicago's most beautiful, dazzling interiors.

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Chicago: City Minibus Tour with Optional Architecture Cruise

Guided tour2 - 4 hours4.6 from 173 reviewsfrom $49

Discover downtown Chicago, as well as some nearby neighborhoods on a minibus tour. Choose to add an architectural cruise of Chicago for the best way to see Chicago fro...

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Embers of the Windy City: Chilling Chicago Ghost Tours

Guided tour1 hour4.5 from 50 reviewsfrom $27

Discover the chilling side of Chicago on a haunted walking tour! Explore historic sites, hear spine-tingling tales, and meet ghostly mobsters. Join us for a night of t...

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Chicago: Downtown Chicago Skyline Helicopter Tour

Guided tour7 - 20 minutes4.4 from 215 reviewsfrom $130

See Chicago from above on a thrilling helicopter flight over the city’s most iconic landmarks. Enjoy stunning skyline and lakefront views with a professional pilot gui...

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Chicago: Field Museum of Natural History Ticket or VIP Tour

Guided tour4.7 from 829 reviewsfrom $29

Explore the world of dinosaurs, ancient Egypt, glittering gemstones, and prehistoric North America at the Field Museum of Natural History.

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Chicago: Offbeat Guided Street Art Tour

Guided tour2 hours3.9 from 41 reviewsfrom $40

Celebrate Chicago's vibrant street art scene on a guided walking tour of the city's most eclectic neighborhoods. Learn about the artists, their art, and the future of ...

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Chicago: Art Deco Skyscrapers Walking Tour

Guided tour1.5 hours4.9 from 31 reviewsfrom $35

Art Deco's lavish materials and geometric ornament epitomized the prosperity and optimism of the Roaring 20s. Learn the history and characteristics of this modern deco...

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Lincoln Park Haunted History Walking Ghost Tour

Guided tour2.5 hours4.8 from 5 reviewsfrom $39

Experience a chilling tour where you are the ghost hunter, guided through Chicago's most eerie sites and immersed in their chilling tales including Lincoln Park and th...

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Chicago: Discover the City's Most Delicious Donuts With Us

Guided tour2 hours4.9 from 99 reviewsfrom $70

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 sample...

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Art Institute of Chicago Express Highlights Tour

Guided tour2.5 hours5.0 from 8 reviewsfrom $84

Unlock the highlights of the Art Institute in just 2 hours with an expert guide—see ancient wonders, iconic masterpieces, and hidden gems on this fast-paced, express tour.

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Chicago Night Driving Tour with Skydeck and River Cruise

Guided tour3.5 hours4.4 from 44 reviewsfrom $204

Experience Chicago's most prominent sights on this night tour with hotel transfers. Enjoy a skyline cruise of the Windy City, and head to the top of the Skydeck observ...

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Chicago: Ultimate City Attractions Bike Tour

Guided tour3 hours4.9 from 58 reviewsfrom $59

Cruise Chicago’s lakefront parks, Millennium Park, Museum Campus & Buckingham Fountain on an engaging Chicago Bike Tour. Enjoy skyline views, amazing stories, & relaxe...

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Chicago: Lakefront Neighborhoods Bike Tour

Guided tour3 hours4.9 from 138 reviewsfrom $59

Join a guided bike tour of Chicago neighborhoods, parks, and beaches of the Near North Side. Pass by the opulent lakeside neighborhoods of the Gold Coast, Old Town his...

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Chicago: Fantastic Lakefront and Museum Campus Segway Tour

Guided tour2 hours4.9 from 160 reviewsfrom $62

Explore Chicago's picturesque Lakefront on a Segway. Chicago's gorgeous lakefront, parks, and skyline are yours to roll through for a fun-filled tour.

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Chicago: Magnificent Mile Walking Tour

Guided tour1.5 hours4.5 from 7 reviewsfrom $35

Learn how the Magnificent Mile developed from a warehouse district into the Champs-Élysées of Chicago. Admire a wide range of architectural styles including Parisian, ...

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Chicago by Night: Skyline, Riverwalk & Navy Pier Lights

Guided tour2 hours5.0 from 1 reviewsfrom $50

Join the nighttime tour led by the local guide to experience the most dazzling side of Chicago. The guide will vividly present the city through captivating stories.

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Sheboygan Arts & Lakefront Segway Tour

Guided tour2 hours5.0 from 1 reviewsfrom $101

Discover the maritime history of Sheboygan on a guided Segway tour. See the lighthouse, schooner remains, shipwreck sites, and the Sheboygan Life-Saving Station.

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Downtown Milwaukee Walking Tour

Guided tour2 hours5.0 from 1 reviewsfrom $16

Explore the unique architecture and streetscape of downtown and learn how Milwaukee's three founders used Lake Michigan, three rivers, and the harbor to create the Mil...

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Chicago E-Bike Tour: Lakefront, Skyline, and Museum Campus

Guided tour2 hours5.0 from 3 reviewsfrom $65

Explore Chicago by electric bike! Ride the lakefront, Grant Park & Museum Campus, discover Chicago stories, and enjoy incredible skyline views with an expert local guide.

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Art Institute of Chicago Highlights Tour & Photoshoot

Guided tour1.5 hours5.0 from 1 reviewsfrom $95

Visit one of the most iconic art museums in the world; see 7 out of the 12 highlights, discover stories behind iconic masterpieces, enjoy a personalized photo shoot an...

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Chicago: Elevated Architecture Walking Tour

Guided tour2 hours4.4 from 5 reviewsfrom $35

Learn the history behind Chicago's famous elevated rail system and admire the city’s architecture on this guided walking tour. See the galleries at the Chicago Archite...

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Chicago: Tiffany Art Glass Works Walking Tour

Guided tour1.5 hours4.3 from 10 reviewsfrom $35

Take a walking tour and learn about the life of Louis Comfort Tiffany. View some of his most well-known glass works as you stroll around Chicago.

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Chicago: Evolution of the Skyscraper Walking Tour

Guided tour1.5 hours3.9 from 11 reviewsfrom $35

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 f...

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Chicago: Street Art Tour

Guided tour1.5 hoursfrom $25

Embark on a journey through the vibrant West Town neighborhood for a tour of the city's unique outdoor street art! Led by your Studio W.I.P. guide, delve into the rich...

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Chicago: Small Group Tour with Skydeck & River Cruise

Guided tour4 hours4.2 from 8 reviewsfrom $189

Explore the highlights of Chicago on a guided tour that includes city highlights, the Skydeck and a boat cruise on the Chicago River.

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Chicago History and Architecture Tour

Guided tour2.5 hours4.4 from 15 reviewsfrom $49

Embark on a guided tour through Chicago's vibrant heart, from the bustling Navy Pier to the iconic Cloud Gate, topped off with the option to enjoy a classic Chicago sa...

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Chicago: Icons Guided Architecture Walking Tour

Guided tour1.5 hours4.4 from 4 reviewsfrom $35

Explore Chicago's iconic architecture on a lively walking tour around the city with an expert guide and visit the galleries of the Chicago Architecture Center.

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Chicago: Crime and Mobster Walking Tour with Ghost Stories

Guided tour2 hours3.1 from 2 reviewsfrom $34

Explore Chicago's dark past on a guided walking tour. Hear tales of gangsters and ghosts, and discover the city's famous landmarks and hidden corners.

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Chicago: Graceland Cemetery Guided Walking Tour

Guided tour2 hours5.0 from 1 reviewsfrom $40

Embark on a guided tour of Graceland Cemetery in Chicago. Learn about the lives of the architects who shaped the city's skyline and hear intriguing stories about the c...

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Chicago Downtown Highlights Private Walking Tour

Guided tour4 hoursfrom $413

Explore the vibrant city of Chicago on a private walking tour led by a knowledgeable local guide

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Chicago: Workers Cottages of Oldtown Triangle Walking Tour

Guided tour2 hours5.0 from 2 reviewsfrom $40

Embark on a captivating architecture walking tour through Chicago's Oldtown Triangle, a neighborhood rich in history and architectural charm.

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Chicago: Wicker Park Architecture Walking Tour

Guided tour2 hours5.0 from 2 reviewsfrom $40

Embark on a guided walking tour of Chicago's Wicker Park and discover the neighborhood's architectural marvels. Learn about the rich labor history that makes Wicker Pa...

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Chicago: Wind and Souls Adults Only Guided Ghost Tour

Guided tour1.5 hours4.4 from 10 reviewsfrom $35

Explore Chicago's haunted past on a spooky walking tour! Visit the Alley of Death, the eerie Congress Plaza Hotel, and hear the tragic tale of the Iroquois Theater.

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Chicago: Best of Attractions Walking Tour +Bike/Kayak Rental

Guided tour2 hours5.0 from 7 reviewsfrom $45

Explore Chicago's best with a guided tour covering Millennium Park, Riverwalk, Michigan Ave, the Chicago Theater, and more. Maximize your experience with a complimenta...

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Chicago: Historic Skyscrapers Guided Walking Tour

Guided tour1.5 hours4.2 from 4 reviewsfrom $35

Explore famous buildings and architecture on a walking tour in Chicago, home to some of the world's earliest skyscrapers. See why Chicago is often called "The Birthpla...

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Chicago: Small Group Tour with Cloud Gate & River Cruise

Guided tour2.5 hours4.4 from 2 reviewsfrom $104

Embark on a small group guided tour through Chicago's vibrant heart, from the iconic Cloud Gate to bustling Navy Pier. Enjoy the Shoreline Architecture Boat Cruise alo...

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Chicago Haunted Interior Architecture Ghost tour

Guided tour1.5 hoursfrom $35

Chicago has beautiful skyscrapers... but did you know they have ghosts?! This walking tour reveals secrets of the skyline and shadowy history. Led by local guides, you...

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Chicago Riverwalk: The River Reversal That Shocked the World

Guided tour2 hoursfrom $65

Experience the astonishing engineering wonder - river reversal. Follow the guide and explore the engineering legend that transformed Chicago from an industrial city in...

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Chicago: A Guided Walking Tour of Lincoln Park Zoo

Guided tour2 hoursfrom $66

Follow the guide to enter one of the oldest zoos in the United States, learn about the interesting habits of various animals, and enjoy the magnificent views of Lake M...

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Chicago: Loop Neighborhood Guided Walking Tour

Guided tour2 hours5.0 from 1 reviewsfrom $60

Explore Chicago’s Loop neighborhood on a guided walking tour. Discover the iconic “L” train, admire historic buildings, and uncover hidden gems and public artworks.

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Chicago: The Loop Walking Tour in Spanish

Guided tour2.5 hoursfrom $20

Experience the best of Chicago’s city center as you stroll past celebrated landmarks, impressive architecture, and cultural attractions while learning the stories that...

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Chicago: Family Friendly Ghost Walking Tour with Local Guide

Guided tour1.5 hours3.0 from 1 reviewsfrom $30

This isn’t just a ghost tour, it’s a story-driven walk through one of Chicago’s most haunted landscapes, where real history and local legend collide.

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Buckingham Fountain: Chicago's Golden Age and Grand Vision

Guided tour2 hoursfrom $58

Discover the story behind one of the world's largest fountains on a guided walking tour of Chicago. Walk through Grant Park, enjoy views of Lake Michigan, and capture ...

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Lake Michigan: The Great Lake That Built Chicago's Fortune

Guided tour2 hours5.0 from 1 reviewsfrom $65

Join a local guide on a hiking trip along the shores of Lake Michigan, and discover how the Great Lakes—through trade, engineering, and innovation—transformed Chicago ...

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Chicago: Downtown Highlights Running Tour

Guided tour75 minutes5.0 from 10 reviewsfrom $49

This spectacular running tour of downtown Chicago enables you to get your miles in and enjoy amazing views and visit the most popular attractions of the city at the same time!

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Chicago: Art Deco Madness Walking Tour

Guided tour1.5 hoursfrom $40

Discover the architectural brilliance of the Roaring Twenties on a walking tour of Chicago's Loop district. Explore 6 stunning Art Deco buildings and uncover hidden gems.

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Chicago: Inside Walking Tour Of Fine Arts Building

Guided tour1.5 hoursfrom $40

Immerse yourself in the enchanting world of Chicago's Fine Arts Building, a hidden gem nestled in the heart of downtown. Learn about the building's rich history and it...

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Chicago: Journey of the Flag Bus Tour

Guided tour1.5 hoursfrom $46

Experience the story of Chicago like never before through a downtown sightseeing adventure.

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Manitowoc Maritime & Lakefront Segway Tour

Guided tour2 hoursfrom $101

Glide along the beautiful coastline of Manitowoc on a Segway tour. Learn about the town's rich history and culture from a knowledgeable guide as you explore the charmi...

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Chicago: Millennium Park Tour with Art Institute Ticket

Guided tour2 hoursfrom $108

Discover the story behind Chicago's Millennium Park on a guided walking tour. Learn about the park's transformation and enjoy included admission to the Art Institute o...

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Fish Creek Segway Tour

Guided tour50 minutes5.0 from 4 reviewsfrom €47

Experience the beauty of Fish Creek like never before with a Segway glide. Enjoy stunning views of the islands and the towering Niagara Escarpment.

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