Top Chicago Art Tours

Get off the beaten path to experience some of Chicago's best street art on this immersive tour. With a guide in the lead, you can leave the navigation to them and simply take in the scenery. Listen to in-depth commentary focused on the street-art community, the artists, and the history and meaning behind the art.

The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.

Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat, O’Keeffe, and many more. As you go, your guide will share the stories behind the masterpieces, and will help bring the history of the museum and its collection to life.

Discover one of Chicago’s top architectural marvels when you explore Frank Lloyd Wright’s UNESCO-listed Frederick C. Robie House, located right on the University of Chicago’s campus. Considered a masterpiece of Prairie School architecture, the building is famed for its cantilevered roof and rich wood details. Save money when you book tickets to the house in advance; call ahead to reserve a space on one of the museum’s frequent, small-group public tours.

Explore the art glass crafted and designed by the Tiffany Glass and Decorating Company during this 2-hour walking tour in Chicago. Following an expert guide from the Chicago Architecture Foundation, visit 4 late 19th-century landmarks that contain glass works by Louis Comfort Tiffany and his contemporaries. This sophisticated, informative tour is a must-do for history and architecture fans. The tour includes general admission to the Art Institute of Chicago for the tour plus 1 other day. 

Discover the ‘dark side’ of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine’s Day Massacre, learn about ‘The Enforcer’s Safe,’ and stop by local watering holes.

Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside neighborhoods. You have a chance to get out and visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.

Admire the incredible façades and intricate interiors of the Windy City's 1920s art deco and art moderne buildings during this architecture walking tour of Chicago. Uncover the history of Chicago art deco architectural along with the city's influential role in the development of this iconic artistic style, as you get an up close and personal look at its wealth of gorgeous period buildings. This art deco Chicago walking tour also includes a certified guide.

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.

Enjoy a quintessential Chicago experience when you go on an architecture-themed river tour. Pick from multiple convenient start times, and board your vessel—the Lady Liberty—directly from the Chicago Riverwalk. Your trained docent guides will give you a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and you can spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

One of the fantastic things about Chicago’s downtown is its underside consisting of hidden streets, train stations, and pedestrian tunnels. It’s filled with innovative and interesting design features you won’t find in any other city, and much of it has its roots from more than a century ago! Do you know who appreciates Chicago’s underbelly? Rats! These fascinating creatures have a lot in common with Chicago: they’re scrappy, they’re adaptable, they’re resilient, and their fates are thoroughly interconnected. Underground Chicago (Plus Rats!) is a fun, one-of-a-kind tour experience where you’ll explore an underground labyrinth discovering features people rarely notice and the stories behind them. Along the way, you’ll hear lots of surprising RAT FACTS that will likely give you a new appreciation for these critters. I hope you can join for this unique tour experience showcasing Chicago’s infrastructure and urban wildlife!

Follow an artist through Chicago’s vibrant art scene, and you’ll see the city with new eyes. On this guided tour, you’ll walk through West Town’s B-Line, a modern art corridor with 1970s origins, home to some of the best street art in the world. You’ll hear facts, trivia, a few wild stories and more, finishing up with optional beers—and crafts!—at a hyperlocal brewery.

Get ready to discover the storied architecture of Chicago. You’ll take the first elevator ride of the morning up to Skydeck at Willis Tower to see the city from a birds-eye prime vantage spot. Journey back to street level for an immersive tour of the Loop guiding you from the iconic ‘L’ train circling downtown Chicago to the city’s impressive Art Deco architecture. This insider’s look will supply you with the history to truly appreciate these colossal structures. A 90-minute river cruise awaits at the end of the tour taking you from the Chicago River to Lake Michigan.

This is the only tour in Chicago that explores 'Ferris Bueller's Day Off' from the perspective of art. It's also the only tour that immerses you in the actual artwork featured in the 1986 American teen comedy. Over the course of the tour, you'll visit 3 floors of the museum, see 16 pieces of art, and leave with an appreciation of the works, their relationship to characters, and their placement in the camera's frame.

We find quality art from around the city by local artists that have significance towards local artists. Unique opportunity to appreciate homegrown art from local Chicagoans and to receive artistic inspiration.

This tour provides information and history beyond just the art and landscape of Millennium Park. It's a comfortable stroll through one of the most visited parks in Chicago. Our professional tour guides will share the history of the people who made the park possible as well as the world-renowned artists and architects who curated Millennium Park into the icon it is today.

You are invited to come along for an adventurous exploration experience led by one passionate, 5-STAR tour guide, on a mission to reveal the remarkable history, mystery, comedy and tragedy that embody The Windy City! Interact with Chicago in new found ways across two-hours of downtown discoveries! Expect an engaging, entertaining and wide-eye-opening experience, full of knowledge nuggets and tater thoughts you simply won't find anywhere else! During our loop around "Da Loop" we will peel back the layers of this Great Big Onion Town step-by-step, peeking in and out of extraordinary buildings, strolling up and down the block, above the river and below ground. Along the way, walkin', talkin' and gawkin' through the city as our small group takes a closer look at those oft overlooked destinations, uncovering jaw dropping stories and secrets along the way!