Chicago, Illinois Tours & Activities in 2026

Chicago , Illinois

From $ 28.00

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.

Chicago , Illinois

From $ 35.00

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's exclusively offered interiors-themed tours in Chicago for more than a decade, and that's INSIDE CHICAGO WALKING TOURS. Our "World Within: Dazzling Interiors of the Loop" tour is Chicago's first and best architecture interiors tour. Accept no imitations! Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t shown them by a seasoned, in-the-know tour guide. Ranging from stained glass mosaics from the turn of the century to soaring Art Deco spaces from the Roaring 20s, these spaces are some of the most beautiful in the city -- and open to us to explore!

Chicago , Illinois

From $ 32.50

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views of Chicago's renowned skyscrapers from a unique vantage point. This tour offers an amazing opportunity to admire the city's breathtaking skyline and architectural wonders. Sunday – Friday Cruises departing prior to 8:00pm feature recorded narration of the city’s skyline, cruises departing after 8:00pm enjoy some music and the sounds of Lake Michigan aboard our Groove Cruise. November - April 9 tours are 30 minutes. Highlights: Spectacular views of Chicago's famous skyscrapers Onboard bar serving refreshing drinks Relaxing and enjoyable sightseeing cruise Experience Chicago like never before on this serene and scenic Lake Michigan boat tour. Remember to bring your camera to capture those social media worthy photos!

Chicago , Illinois

From $ 35.00

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 Prohibition secrets. This two-in-one experience combines a rich historical walking tour with an exciting award-winning murder mystery game. Perfect for people looking for a history tour of Chicago, and also for people looking for a chance to play and have fun. Explore a City, Solve a Murder! Only on the Chicago Murder Mystery Tour.

Chicago , Illinois

From $ 29.00

Explore over 40 million artifacts, including SUE, the world’s largest, most complete T. rex ever discovered! Discover 23 mummified remains in a recreated Egyptian tomb, our dazzling Gem Hall or journey to the powerful Aztec empire! Meet Maximo our newest titanosaur at over two stories tall! The health of our guests and staff is always our top priority and we welcome you back to safely explore nearly half a million square feet of open gallery space.

Chicago , Illinois

From $ 35.00

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famous and mysterious Chicago Pedway, a system of underground tunnels connecting 40 blocks downtown, popping in and out of buildings to see beautiful and fascinating interior spaces. You'll learn to use this system that most locals don't even fully know or use, and you'll be encouraged to continue exploring Chicago on your own after the tour!

Chicago , Illinois

From $ 35.00

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 most memorable buildings, many of which are featured on this tour. After the World's Columbian Exposition of 1893, Chicago was determined to become a great cultural and commercial metropolis. This tour is a testament to that era's ambitions. See buildings by Daniel Burnham, Louis Sullivan, Holabird and Roche and other noted architects and hear the stories behind the city's architectural gems. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 34.00

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 history, true crime, and haunted mysteries. Expect a sultry and gritty cocktail of Chicago's darkest stories hiding in the shadows of the Loop. From Grant Park to the Alley of Death, your expert local guide will shed light on the city’s secrets. Prepare for thrills and just the right amount of chills.

Chicago , Illinois

From $ 35.00

Get the best of both worlds: explore Chicago’s stunning architecture while uncovering its dark past. Inspired by Devil in the White City, this expert-led walking tour reveals the secrets of the city’s skyline and its shadowy history. The Christmas Version is almost all INDOOR, with 2 Christmas related stops, and the tour ending right by the Christkindlmarket. Led by a passionate local guide, you’ll visit architectural gems and hidden landmarks that boat tours miss bringing Chicago’s rich and eerie past to life.

Chicago , Illinois

From $ 35.00

Want a quick introduction to Chicago’s magnificent architecture? This 90-minute tour takes a comprehensive look at the city’s architectural history by viewing buildings in chronological order, from early skyscrapers to new supertall high rises. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 35.00

View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament. Discover the origins of Art Deco and its hallmark motifs while admiring buildings like the Chicago Board of Trade, One LaSalle Street and the Field Building (now the Bank of America Building) -- all of which are designated Chicago landmarks. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 29.00

One actor has five shots of whiskey and then attempts to perform in a Shakespeare play. New York Times Critics' Pick!

Chicago , Illinois

From $ 35.00

Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art Institute of Chicago, Willis (Sears) Tower and more! Get a brief overview of more than a dozen buildings—as well as Chicago landmarks like Millennium Park, the Loop and the Chicago River—on this whirlwind tour. There are lots of photo opportunities along the way, so be sure to bring your camera! As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 27.00

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This Prairie style masterpiece is now a UNESCO World Heritage Site on the 20th Century Architecture of Frank Lloyd Wright List. Discover the residence Wright described as “a cornerstone of modern architecture” on guided tours that take in both the exterior and interior of the building. Inspired by the expansive landscape of the Midwest prairie, Wright’s Robie House is the most famous of the architect’s groundbreaking Prairie houses. Public tours are available Thursday - Monday. The museum is closed Tuesday and Wednesday. Save when you book directly at Visit to learn more.

Chicago , Illinois

From $ 32.00

Come on our chilling ghost tour presented by US Ghost Adventures! Book Directly With Windy City Ghosts and save $5/person. Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy streets. Our Ghost Tour transports you back in time to an era of gangsters, bootleggers, bank robbers, and jazz babies. Windy City Ghosts nightly Ghost Tours take you through Lincoln Park, a beautiful North Side neighborhood with a twisted past. Learn about the forgotten burial ground that is the foundation of this bustling neighborhood. Check the bathroom mirrors in the Lion House of the Lincoln Park Zoo to make sure the ghost of a Victorian woman in white isn’t standing right behind you. Learn what spirit haunted Al Capone to the end of his days. On our Ghost Tour, you’ll hear the strange and disturbing tales associated with each of our carefully selected tour stops.

Chicago , Illinois

From $ 35.00

Though the Art Deco style throws us back in time, it’s actually a futuristic style — it’s meant to make people in the 1920s think of the future. The gleaming materials, the perfect precision of the details… it’s the epitome of glitz, glam, and elegance. On this tour, you’ll walk in the footsteps of those high on the potential of the future, before the infamous Crash of ‘29. We’ll explore several stunning interior spaces within the Loop and near the Chicago River, going inside not only the great Art Deco buildings of the Loop, but also a few buildings you’ll recognize from popular boat tours. But the great thing is that you’ll go where most boat tour guests won’t ever go: inside these gorgeous Art Deco buildings, where you’ll be amazed by the beauty that people don’t know is right there behind closed doors.