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Segways are fun and easy to ride!

Experience Chicago in a new way on this small-group Segway tour. Visit Chicago’s "front yard," and see more of the sights in less time. Glide along the fragrant floral paths of Grant Park to the famous Buckingham Fountain. Then, travel along the banks of Lake Michigan to the Museum Campus for top-notch views of the city’s iconic skyline. Guided Segway training and helmets are included, making this a beginner-friendly tour.

Chicago Landmarks & Museum Campus Small Group Segway Tour

2 hoursFree Cancellation

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Enjoy waterfront views of downtown Chicago on a 2-hour brunch cruise through the heart of the city. Board a luxurious yacht at Navy Pier then relax on deck with a complementary mimosa. Find a comfortable spot on the three climate-controlled observation decks, and enjoy a sumptuous buffet while the onboard DJ spins a leisurely afternoon playlist. Capture unforgettable images of downtown skyscrapers and architectural landmarks as you navigate along the historic shoreline, then loop back and finish your outing at the bustling Navy Pier.

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

2 hoursFree Cancellation

Private Arrival Transfer from Chicago Airports (ORD) (MDW)

Ensure a hassle-free arrival at Chicago O'Hare International Airport (ORD) or Midway Airport (MDW) with this private transfer service to your downtown Chicago hotel (or farther-flung Chicagoland destination). Take the stress out of finding a taxi at Chicago's busy airports and book a private vehicle in advance. Travel in style by luxury sedan or SUV that can accommodate up to six passengers.

Private Arrival Transfer from Chicago Airports (ORD) (MDW)

1 hourFree Cancellation

Navy Pier 4 - Ride Pass

Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO

Likely to Sell Out

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Discover a side of the Windy City that many visitors overlook—and immerse yourself in its vibrant street art scene—on this urban walking tour. With your art-expert guide in the lead, you can focus on soaking up the city's ambiance, and spotting artworks and murals you may not have discovered on your own. As you go, listen to in-depth commentary about the artists and artworks, and explore some of the city's hippest neighborhoods.

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

2 hoursFree Cancellation

Nat "King" Cole landmark - Nat lived in this house until he was too big to stay! L.A. and television called him!

African American Heritage Tour of Chicago

4 to 7 hoursFree Cancellation

Chicago Food Tour

Get to know the “must eats” in Chicago's buzzing Loop District on this small-group or private walking tour. As you explore, listen to in-depth commentary from your guide about the culinary history of Chicago, and get a taste of the city's most iconic foods, from hot dogs to deep-dish pizza. You'll enjoy personalized attention and the chance to chat about your favorite tastings, all while admiring Chicago landmarks along the way.

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

2 hoursFree Cancellation

Price varies by group size

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

Delve into the rich history and notable architecture of one of Chicago’s most luxurious neighborhoods—and learn insider stories as you go—with this self-led smartphone audio walking tour. Upon booking, download the app and set off at a time and pace that works best for you. Discover Gold Coast landmarks from historic piano bars to the original Playboy Mansion, and stop and start the tour whenever you like.

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

Feel the presence of the unseen as we wander through haunted history under the moon's glow.

Discover some of the Windy City’s spookiest ghost stories—and step back in time to the era of gangsters, bootleggers, jazz performers, and more—on this small-group walking tour. Meet your guide in Chicago’s Lincoln Park neighborhood, and set off after dark. You’ll visit supposedly haunted former burial grounds, pubs, theaters, and more—and will hear about macabre legends and unexplained happenings as you go.

Embers of the Windy City: Chilling Chicago Ghost Tours

1 hourFree Cancellation

111 E Wacker Drive

Enjoy an immersive way to discover Chicago's more recent architectural heritage with this small-group walking tour. Led by your architectural expert guide, you'll discover many of the Windy City's modern, postmodern, and other newer structures, including works by architects like Mies van der Rohe, Bertrand Goldberg, and beyond. As you go, your guide will point out the buildings many visitors overlook, and share stories from their history you wouldn't otherwise hear.

Chicago Walking Tour: Modern Architecture

1 hour 30 minutesFree Cancellation

Special Offer

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about the city’s past. See the stunning interiors and exteriors of noteworthy buildings and leave with a comprehensive understanding of the city’s downtown.

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

2 hoursFree Cancellation

Beverly Hills

Explore Chicago like a local—and visit the city’s distinctive, characterful neighborhoods, in addition to its major landmarks—on this Half-day tour. Set off from downtown with just a small group for company, and leave the driving to your guide—you’ll explore dozens of Windy City neighborhoods, from Hyde Park and Bronze Ville to Lincoln Park and the Gold Coast. Learn all about Chicago culture and history as you go.

Small-Group Tour of Chicago Neighborhoods: North and South Side

4 hours 30 minutesFree Cancellation

Likely to Sell Out

The Chicago Theatre Tour Experience

Enjoy the opportunity to go behind-the-scenes at one of the Windy City's most storied venues on this insider tour of the Chicago Theater. Let your guide lead the way, as you hear about the theater's architecture, history, and famous performers throughout the years. Stand on the famed stage and take in the atmosphere, and see artist signatures from notable performers, including Frank Sinatra and Dolly Parton. A great activity for fans of music and live performance.

The Chicago Theatre Tour Experience

1 hour to 1 hour 15 minutes

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

Chicago is renowned for its wealth of spectacular architecture—and this small-group tour gives you the special chance to discover building interiors that most visitors overlook. In the afternoon, meet your guide in Downtown Chicago, and get ready to discover the interiors of five of the city’s most striking art deco skyscrapers. As you go, soak up the skyline views, and learn more about the city’s unique architectural history.

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

1 hour 30 minutesFree Cancellation

Likely to Sell Out

Historic Homes and Cottages of Wicker Park Walking Tour

Discover one of Chicago’s most picturesque, historic neighborhoods—and learn all about the buildings that make it an architectural standout—on this small-group walking tour of Wicker Park. Meet your guide in the morning, and set off on foot: you’ll discover the 19th-century workers’ cottages that fill the neighborhood, will admire local landmarks like mansions and historic baths, and will learn all about the city’s architectural history.

Historic Homes and Cottages of Wicker Park Walking Tour

1 hour 30 minutes

Chicago Walking Tour: Connecting Past and Present

Chicago is world-renowned for its architecture—and this small-group walking tour offers the ideal introduction to its iconic buildings, its architectural eras, and the starchitects who have left their impression on the city. Meet your guide at the Chicago Architecture Center and set off on foot: you’ll discover highlights like the Wrigley Building and Marina City, will see works by Renzo Piano and Frank Gehry, and will learn all about Chicago history.

Chicago Walking Tour: Connecting Past and Present

1 hour 45 minutesFree Cancellation

Historic Loop Skyscrapers

Explore the Loop's famous architecture—and learn insider facts and stories that you wouldn't encounter if exploring alone—on this small-group walking tour. Led by your Chicago Architecture Center–certified guide, you'll discover some of the city's oldest skyscrapers, dating from the late 19th and early 20th centuries. Admire the Rookery building, see the Marquette building, and much more, all while soaking up the city's ineffable energy.

Chicago Walking Tour: Historic Skyscrapers

1 hour 30 minutesFree Cancellation

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Chicago’s “L,” or elevated train, is an icon of public transportation and a major feature of the Loop neighborhood. On this interactive tour, you’ll learn about the railway’s history while experiencing it as a rider. Meet your guide in the morning and set off with just a small group for company. As you ride between stops, you’ll also view Chicago icons like the Willis Tower, and will learn about the city’s architectural history.

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

2 hoursFree Cancellation

Drunk Shakespeare Ticket – Chicago

Drunk Shakespeare Ticket – Chicago

1 hour 30 minutesFree Cancellation

Likely to Sell Out

Workers Cottages of Oldtown Triangle Walking Tour

Leave behind Chicago’s buzz and see the Windy City as it used to be, some 150 years ago. The Oldtown Triangle—one of the most beloved ‘hoods in the city—survived the Great Chicago Fire of 1871, and it still stands today as a beacon to history. With your guide at the helm, you’ll witness fantastic architecture, national landmarks, and hear stories of the city’s often wild past.

Workers Cottages of Oldtown Triangle Walking Tour

1 hour 45 minutesFree Cancellation

Chicago Cultural Center

Discover Chicago architectural treasures—and immerse yourself in the Windy City's history—on this small-group walking tour. Your focus is the iconic stained glass pieces crafted and designed by the Tiffany Glass and Decorating Company. Following your guide from the Chicago Architecture Center, visit four late-19th-century landmarks that contain glass works by Louis Comfort Tiffany and his contemporaries. This in-depth, insider tour is a must-do for history and architecture fans.

Chicago Walking Tour: Tiffany Treasures

1 hour 30 minutesFree Cancellation

Museum of Illusions Chicago Admission Ticket

Step into the captivating realm of illusions, where reality is never exactly as it appears. Museum of Illusions is a one-of-a-kind, visual, sensory, and educational experience designed to engage your sense of wonder and challenge perceptions through the science behind optical illusions. We offer over 50 immersive, hands-on exhibits to explore. Our illusion rooms, installations and holograms let you defy gravity, grow and shrink your body, walk into a life-size kaleidoscope, and play tricks on your senses at every turn. It’s a mind-bending journey that deceives the senses and reveals how the brain interprets reality.

Museum of Illusions Chicago Admission Ticket

45 minutes to 1 hour 30 minutes

Chicago True Crime and Gangsters Tour

Our goal is to disturb and unsettle you of whatever assumptions you may have about Chicago. We do so with our entertaining and brilliantly researched experiences, that highlight the historic gangster past of Chicago, and also shares the hidden beauty, natural wonders, and cultural highlights of America's third-biggest city. Guests walk away more historically oriented travelers, with a reason to visit Chicago again.

Chicago True Crime and Gangsters Tour

1 hour 30 minutesFree Cancellation

Downtown Chicago TV and Movie Sites Guided Walking Tour

Downtown Chicago TV and Movie Sites Guided Walking Tour

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Top Attractions in Chicago

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Entrance to Chicago Riverwalk surrounded by skyscrapers, Chicago

Attractions

Chicago Riverwalk

The Magnificent Mile in Chicago on a warm spring day.

Attractions

The Magnificent Mile

The statue of a lion at the entrance to Art Institute of Chicago, USA

Attractions

Art Institute of Chicago

A woman exploring the view from the Skydeck Chicago at Willis Tower.

Attractions

Skydeck Chicago at Willis Tower (Sears Tower)

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People Also Ask

What are the best art and culture tours in Chicago?

There are plenty of high-quality Chicago art and culture tours to choose from. Looking at ratings and reviews given by previous customers, these are the best tours available right now:

What are the most affordable art and culture tours in Chicago?

Chicago art and culture tour prices vary depending on duration and inclusions. If you're looking for high-quality experiences on the lower end of the price range, these are the best tours to book now:

Are guided art and culture tours in Chicago worth it?

Yes, guided art and culture tours in Chicago are considered worth it by travelers. They provide an engaging way to explore the city's diverse neighborhoods, world-class museums, and iconic architecture with insights from knowledgeable local guides. Whether you're cruising the river, touring the Art Institute, or sampling food in Chinatown, these tours offer a deeper understanding of Chicago's creative and cultural identity.

Per one customer who booked the Chicago in a Day: Food, History & Architecture Walking Tour, "David was an awesome guide of the city. Chicago is an amazing town and we learned so much. The food and architecture is top-notch. We had a great time and our group was fun!"

What should I know before booking art and culture tours in Chicago?

What are the best tips for enjoying art and culture tours in Chicago?

What Chicago art and culture tours are one hour or less?

Even if you're short on time, you can find fun Chicago activities to fit your schedule. Here are some of the best Chicago art and culture tours to enjoy in an hour or less:

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