Chicago Cultural Tours

Discover Chicago's rich culture with top tours including architectural cruises, food walks, museum visits, and secret interior tours. Book your adventure today!

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2 Hour Bridgeport /Stockyard Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Bridgeport /Stockyard Tour, led by H

From $45.00 USD

2 Hour Bronzeville, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Bronzeville, led by Historian Dilla,

★ 5.0 (2)

From $45.00 USD

2 Hour Chatham, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Chatham, led by Historian Dilla, who

From $45.00 USD

2 Hour Englewood, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Englewood, led by Historian Dilla, w

From $45.00 USD

2 Hour North Lawndale, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like North Lawndale, led by Historian Dil

From $45.00 USD

2 Hour Pilsen and Little Village, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Pilsen, led by Historian Dilla, who

From $45.00 USD

2 Hour Private Chicago Soul House Tour

This is not a bus tour, 90% of our tours are 11 people or less, as we specialize in small, personalized group tours. This gives us the space and time to take pi

★ 4.0 (5)

From $65.00 USD

2 Hour Pullman/Roseland Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Pullman, led by Historian Dilla, who

From $45.00 USD

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Looking for fun things to do in Chicago? Look no further! Join one of our professional guides on a scenic 6-8 mile Chicago Segway tour. Glide effortlessly throu

★ 5.0 (385)

From $64.40 USD

2-Hour Chicago's Chinatown History and Culture Tour

Discover the heart of Chicago’s Chinatown with your authentic history and culture tours, exclusively offered by the official Chinatown Visitor Center. Led by ex

★ 3.8 (5)

From $30.00 USD

90 minute Chicago's Chinatown History and Culture Tour

Explore the highlights of Chicago’s Chinatown in just 90 minutes with our expert-guided History and Culture Tour. This tour takes you through iconic landmarks,

From $30.00 USD

A Woman's Place: The Chicago Women's History Walking Tour

Forget the history you learned in school—Chicago’s story looks very different when told through the women who helped shape it. On this captivating 2-hour walkin

From $31.50 USD

African American Heritage Tour of Chicago

This tour visits the homes of Louis Farrakhan, the former home of Elijah Muhammad and the former home of Muhammad Ali. We will pass by and take pictures at the

★ 4.4 (144)

From $125.00 USD

Art Institute of Chicago Skip-the-Line Exclusive Guided Tour

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour exclusive guide

★ 5.0 (344)

From $90.10 USD

Bike Tour of Chicago's Lakefront Neighborhoods

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excell

★ 4.9 (263)

From $59.00 USD

Bucktown and Wicker Park’s 606 Trail: A Walking Tour

The Bloomingdale Trail was built on a former railway line that once served as the industrial backbone of Chicago's north side. On this self-guided audio tour th

From $5.00 USD

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mil

★ 5.0 (2)

From $11.75 USD

Chicago Architecture, History and Culture Loop Walking Tour

Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, inc

★ 5.0 (3)

From $50.00 USD

Chicago Audio Guided Walking Tour 3h and 25 Audio Commentaries

Chicago, a city with undeniable charm, awaits you for a walking exploration of its 25 must-see attractions. From the Riverwalk to Marina City to the famous Clou

From $7.00 USD

Chicago City Tour with Architecture River Cruise Option

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago

★ 4.8 (736)

From $49.95 USD

Chicago Crime, Mobsters & Ghosts Walking Tour

Join us along the historic streets and alleys of Chicago as we walk among the spirits of mobsters and ghosts of the condemned. This tour is for lovers of histo

★ 4.7 (461)

From $34.00 USD

Chicago Custom Private Walking Tour with A Guide ( Private Tour )

Chicago can sometimes feel inaccessible to visitors, but a private walking tour with a local guide takes the mystery out of the city. This personalized tour foc

From $129.34 USD

Chicago Downtown Sports History Adventure

Uncover the essence of Chicago's sports culture on this guided tour through the downtown area. Learn about the city’s iconic sports figures, explore fascinating

From $5.00 USD

Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets

Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary thea

From $263.00 USD

Chicago Family Food and Bike Tour with Top Attractions

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in Ame

★ 4.8 (101)

From $79.00 USD

Chicago Gangsters and Prohibition Private History Tour

Discover Chicago’s infamous gangster past on a private, fully personalized tour through the city’s historic Prohibition-era streets. Travel in comfort with your

★ 2.3 (3)

From $114.05 USD

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on your phone. -Tour at y

★ 4.8 (5)

From $9.75 USD

Chicago in Spanish. Architecture. Mafia, Interiors, Underground

Discover the real Chicago with those who really know it! At ChicaGo Turismo we transform a simple tour into an unforgettable experience. More than visiting mon

★ 5.0 (11)

From $45.00 USD

Chicago Insider Segway Tour

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chica

★ 4.9 (52)

From $64.80 USD

Chicago Jewish History Landmarks Private Guided Walking Tour

Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden

From $227.00 USD

Chicago Landmarks and Museum Campus Small Group Segway Tour

Looking for fun things to do in Chicago? Explore the city with one of your professional guides on a scenic 6-7 mile tour. Begin your adventure by gliding throug

★ 5.0 (239)

From $70.00 USD

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discover

★ 4.8 (131)

From $86.68 USD

Chicago Loop Self-Guided Audio Tour: Architecture & History Walk

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skysc

★ 5.0 (5)

From $9.99 USD

Chicago Murder Mystery Tour

You will solve a murder as you learn real Chicago history! Play detective as you unravel a murder mystery, and learn about Chicago's true crime legends and Proh

★ 5.0 (755)

From $35.00 USD

Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

Channel your inner Sherlock Holmes in this murder mystery hunt around The Chicago Loop. In the “Murder in The Chicago Loop” transports you to the year 1923.

★ 5.0 (1)

From $59.00 USD

Chicago Pope Leo XIV's Roots Tour

Discover the unique journey of Pope Leo XIV through Chicago on this interactive bus tour. Visit his childhood home and childhood church in the suburb of Dolton

From $79.00 USD

Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.

★ 4.9 (207)

From $539.00 USD

Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver,

From $223.41 USD

Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenie

From $1,200.00 USD

Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle

Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Millennium Park and Riverwalk! Snap a picture by the famous Cloud

From $24.99 USD

Chicago Seadog River & Lake Architectural Tour

Soak in unobstructed views of Chicago’s world-famous architecture from the water with an exciting ride on our Seadog River and Lake Architectural Tour! Sail thr

★ 4.5 (301)

From $41.65 USD

Chicago Self-Guided Audio Tour

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as y

★ 3.9 (9)

From $6.00 USD

Chicago to Mackinac Island Scenic Tour

Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel thro

From $685.00 USD

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Learn how Art Deco

★ 4.9 (102)

From $35.00 USD

Chicago Walking Tour: Historic Skyscrapers

Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build them and

★ 4.8 (72)

From $35.00 USD

Chicago Walking Tour: Historic Treasures of Chicago

Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the

★ 4.9 (445)

From $35.00 USD

Chicago Walking Tour: The Magnificent Mile

Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping distric

★ 4.9 (51)

From $35.00 USD

Chicago Walking Tour: Tiffany Treasures

Learn about the life and work of Louis Comfort Tiffany as we visit some of Chicago’s most magnificent art-glass and mosaic installations, each designed and craf

★ 4.7 (47)

From $35.00 USD

Chicago West Loop Sweet Treats Food Tour: Donuts, Cookies, & More

We begin at a local shop synonymous for their quality donuts––Do-Rite Donuts. From there we’ll walk the Randolph corridor, learning about the history of Chicago

★ 5.0 (89)

From $70.00 USD

Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours

★ 4.9 (797)

From $79.99 USD

Chicago's Secret Interiors Architectural Walking Tour

We invite you to step inside the city’s most exclusive, jaw-dropping architectural treasures. Led by an expert local storyteller, you’ll discover breathtaking h

★ 4.9 (47)

From $35.00 USD

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-

★ 4.9 (274)

From $59.00 USD

Chicago’s Millennium Park Self Guided Audio GPS Walking Tour

Our tour will take you through Millennium Park, starting at the Millennium Park Welcome Center. We’ll wander past shining sculptures, playful fountains, and pea

From $9.75 USD

Chinatown Food Tour

Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore the nei

From $98.00 USD

Chinatown History and Culture Tour

Winner of 10 Best History Tours by USA Today in 2026, and the "ORIGINAL" Chinatown tour since 2001. Discover the history, culture, and hidden stories of Chica

From $25.00 USD

Discover Chicago: A Self-Guided Walking Tour

Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant c

★ 2.0 (1)

From $3.52 USD

Downtown Chicago Loop Walking Tour (Private)

Discover the stories, styles, and spirit that built Chicago into the architectural capital of the world. On this walking tour through the Loop, you’ll explore t

From $27.00 USD

Field Museum Basic Admission Ticket Plus VR Experience

A visit to the Field Museum unlocks a world of discovery with access to captivating exhibitions like the Griffin Halls of Evolving Planet and the iconic SUE the

From $42.00 USD

Guided Audio Road Trip Route 66

Live the mythical Route 66 as it should be: at your own pace, with freedom and with the feeling of being walking a living history. This audio guide accompanies

★ 1.0 (1)

From $29.40 USD

Historic Homes and Cottages of Wicker Park Walking Tour

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty, from the mun

★ 5.0 (51)

From $45.00 USD

History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walking among gigantic towers of downtown, we will learn why and ho

★ 5.0 (24)

From $33.00 USD

Hyde Park Walking Tour History Race and Urban Change

Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat

From $5.00 USD

Inside Tour of Chicago’s Fine Arts Building

Take a time travel journey inside Chicago's best-kept secret: a 125-year-old architectural marvel. This extraordinary building was envisioned by renowned archit

★ 4.9 (28)

From $45.00 USD

Intro to Chicago Architecture

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from ea

★ 5.0 (24)

From $35.00 USD

Lake Michigan Fireworks Cruise in Chicago

No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close and personal every Wedne

★ 4.2 (142)

From $60.00 USD

Logan Square Walking Tour Experience

An amazing, local's guided tour of one of Chicago's coolest neighborhoods. Learn the history and get advice from a local who knows this area and make your Chica

From $35.00 USD

Mackinac Island Private Day Tour from Chicago

Discover the charm of Mackinac Island on a delightful journey from Chicago, blending history, culture, and stunning landscapes. Without cars, the island embrace

From $1,350.00 USD

Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game

Venture along Michigan Avenue on an interactive tour to uncover Chicago's hidden gems and iconic landmarks. Dive into the city's rich history, answer trivia, an

From $17.04 USD

One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, wher

★ 3.0 (2)

From $450.00 USD

Original Chicago Prohibition Bus Tour

Our Original Bus Tour is a deep dive into Chicago's most notorious era. Taking you to neighborhood gems you may not find on your own, grab a drink and enjoy the

★ 5.0 (4)

From $55.00 USD

Pilsen Chicago Walking Tour: Street Art & Mexican History

Discover Pilsen, one of Chicago’s most vibrant neighborhoods, known for its colorful street art, rich Mexican heritage, historic architecture, and thriving loca

★ 5.0 (5)

From $35.00 USD

Podcast Tour Chicago The Promised Land and the Black Metropolis

Step into the vibrant, resilient heart of Chicago's South Side. On this immersive journey through Bronzeville, you will uncover the epic story of the Great Migr

From $5.63 USD

Private & All-Inclusive Chicago Downtown Highlights Walking Tour

On this private walking tour our expert local guide will take you to see some of Chicago’s best-known attractions! The day will begin with you meeting with yo

From $223.00 USD

Private and All-Inclusive Tour of Chicago

Experience the best of Chicago on this private full-day city tour designed for a fun, stress-free day of exploring. Enjoy comfortable hotel pickup, ride in a sp

★ 5.0 (1)

From $750.00 USD

Private Architectural Walking Tour in Chicago Historic Residences

This private architectural walking tour in Chicago explores residences that reflect the city’s design evolution. You will begin along Lake Shore Drive, where ea

From $869.00 USD

Private Architectural Walking Tour in Chicago Loop Landmarks

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through the Loop’s architectural wonders with our Loop Architecture

From $869.00 USD

Private Chicago Architecture Walking Tour

Discover the heart of Chicago’s architectural legacy on this guided walking tour through the historic Loop District. Step back in time as you explore some of th

★ 4.8 (6)

From $211.00 USD

Private Chicago Guided Tour with Hotel Pickup

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most

★ 5.0 (5)

From $785.27 USD

Private Chicago History Museum Tour

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life

★ 5.0 (27)

From $162.50 USD

Private Chicago Loop Architecture Walking Tour

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic sky

★ 5.0 (13)

From $180.00 USD

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where archite

★ 5.0 (1)

From $1,029.00 USD

Private Family Walking Tour in Chicago Loop Cultural District

This private family walking tour in Chicago introduces the cultural and architectural identity of the Loop district. You will begin in the financial center, whe

From $669.00 USD

Private Historical Ghost Walking Tour in Chicago Lincoln Park

This private historical ghost walking tour in Chicago explores stories rooted in the city’s layered past. You will walk through Lincoln Park, an area shaped by

From $869.00 USD

Private History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walking among gigantic towers of downtown, we will learn why and ho

From $144.00 USD

Private Wicker Park and Bucktown Walking Tour

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time to see a

★ 5.0 (3)

From $195.00 USD

Prohibition Chicago: Myth vs. Reality Walking Tour

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't alw

★ 5.0 (1)

From $35.00 USD

Resilience and Revolution: Audio Tour of Chicago’s Black History

Chicago is inseparable from its Black history, where local pioneers helped shape the city’s story. On this self-guided audio tour through downtown Chicago, you’

From $14.99 USD

Route 66 Multi Day Tour from Chicago to Los Angeles

Travel the legendary Route 66 in 14 unforgettable days - from Chicago to Los Angeles across eight states, discovering over 450 handpicked points of interest. Ex

From $10.00 USD

Self-Guided Podcast Tour Chicago: The Loops Monumental Canvas

Discover how a city of rigid steel and glass skyscrapers transformed its streets into a world-class, democratic art gallery. On this immersive walking tour thro

From $5.63 USD

Skip the Line Chicago Art Institute Tour Semi-Private 12ppl Max

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour semi-private (1

★ 5.0 (248)

From $90.10 USD

Skip-the-line: Art Institute of Chicago Guided Tour

Beat the crowds with an expert art historian guide on this exclusive early morning tour. Immerse yourself among the masterpieces housed within the acclaimed mus

★ 5.0 (629)

From $71.40 USD

Small Group Tour of Chicago Neighborhoods: North and South Side

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that tours multiple neighbor

★ 4.5 (54)

From $125.00 USD

Small Group Walking Tour of Chicago The Loop

Explore Chicago with a passionate local guide on a small-group walking tour that takes you beyond the city's most recognizable landmarks. As you stroll through

From $25.00 USD

Taste of Chicago's Chinatown Food Tours

Best Chinatown Food and Walking Tour in town! The Chicago’s Chinatown Food and Walking Tour is a 3-hour immersive culinary and cultural experience designed to h

★ 5.0 (3)

From $85.00 USD

The Chicago Theatre Tour Experience

A 60-75-minute guided, behind-the-scenes exploration of the historic Chicago Theatre, one of the city’s most iconic landmarks. Stand on the famed Chicago theat

★ 4.0 (58)

From $32.00 USD

The Deep Pockets Of Graceland Cemetery Walking Tour

Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic

★ 4.8 (11)

From $45.00 USD

Visit in French: The Evolution of the Skyscraper

This unique tour will give you a complete overview of Chicago's architecture. While listening to the history of the city, you will see, in chronological order,

From $35.00 USD

Walking Prohibition Tour

Get a closer look into how alcohol flowed through the streets of Chicago! From the “down and dirty” gangster hangouts, to the “jackets required” establishments

From $45.00 USD

Welcome to Chicago: The Essential City Tour with photo stops

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their histo

From $35.00 USD

Wicker Park Walking Tour History Trivia and Local Flavors

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walk

★ 5.0 (1)

From $40.00 USD

Workers Cottages of Oldtown Triangle Walking Tour

This tour will show you many of these delightful cottages and the different styles they were designed and constructed in. You will also learn about their histor

★ 5.0 (57)

From $45.00 USD