Top Illinois Historical Tours

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

Immerse yourself in Chicago’s rich and dynamic African American heritage during this half-day tour. Highlights include interior visit to an African American museum, a stop at the birthplace of gospel music in Bronzeville, and a look at the Obama home in Hyde Park and Jennifer Hudson's childhood home.

Swap the standard Chicago itinerary for the chance to experience a whole different side to the city. Walk in the footsteps of Al Capone and John Dillinger while hearing tales of Chicago's haunted past. This walking tour takes you to prohibition-era speakeasies, sites of real life mob shootouts, and provides special access to places tied to historical events that have shaped Chicago.

Explore a new side of Chicago and the city'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, John Dillinger, and more famous figures hung out. There are ample chances to get out of the bus and pose for pictures in front of a historic courthouse, among other infamous sites.

Delve into the world of natural history with admission to Chicago’s Field Museum. Choose general admission or upgrade to visit one or more special exhibits. Spend as long as you like exploring the museum's extensive collection of artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Also take advantage of daily tours led by knowledgeable Field Museum docents, free with admission.

Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue, State Street, and the vibrant Loop area. Revisit the heyday of the skyscraper and visit stunning, art deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.

The Field Museum of Natural History is one of Chicago’s most-visited museums—and this package deal offers a way to beat the crowds and see its top exhibitions without stress. Secure your tickets before you travel, arrive an hour before the galleries open to the public, and explore in the company of a museum docent. You’ll see collection highlights like Sue the Tyrannosaurus Rex, the Griffin Halls of Evolving Planet, and much more.

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.

Book in advance to take this popular tour that details the mob history of Chicago during the Prohibition Era (1920s-1930s). Learn about the exploits of gangsters like Capone, Dillinger, Moran, and others as you travel by minibus to sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine's Day Massacre. Your guide adopts gangster attire and characteristics that add dramatic flair to the historical commentary.

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Discover the birthplace of one of the 20th century’s most revered authors on this tour of Oak Park, Illinois’ Ernest Hemingway Birthplace Museum. Pick from a range of convenient start times, make your own way to the museum, and head right inside with the included admission. You’ll see where Hemingway was born, will learn about his family and early years, will explore the house’s restored rooms, and otherwise immerse yourself fin Hemingway’s life and times.

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chicago River while hearing chilling tales of disasters, infamous criminals, and eerie legends tied to the city’s past. This relaxed river cruise blends atmospheric storytelling with some of the best nighttime views of Chicago’s renowned skyline and landmarks. Grab a drink from the onboard bar, settle in, and let the city’s shadowy history unfold as you cruise through the heart of downtown. By the end of the journey, you’ll have experienced Chicago’s skyline in a whole new way—while uncovering the chilling events, legends, and mysteries that shaped the city. Please arrive 30 minutes in advance!

Skip the guesswork and discover the real haunts of Capone, Dillinger, and The Outfit on a walking tour that then also you shows how those same streets become movie stars. Walk the city corners seen in *The Untouchables* and *Public Enemies,* and hear how Chicago wrote the script for American gangster history. This isn’t just another sightseeing tour—it’s a front-row seat to crime, cinema, and the city that made them both.

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.

Chicago is famous for its architecture, and the best way to see it is on a cruise down the Chicago River. Glide by historic and modern marvels like the Civic Opera House, Wrigley Building, and Willis Tower from the comfort of an open-deck boat. Live narration reveals each building’s fascinating history, so you'll learn more than you would just observing on your own.

Maximize your Chicago sightseeing on a river cruise—and travel aboard a unique historical vessel, which other tours don’t offer—on this one-of-a-kind excursion. Pick from different departure times and board a classic Chicago fireboat, which served the city’s fire department from 1937 to 1981. As you sail Lake Michigan and the Chicago River, view architectural highlights including the Wrigley Building and Chicago Lighthouse, and chart the boat’s firefighting history via the on-board displays and commentary.

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.

Exploring Oak Park, Illinois, where Frank Lloyd Wright resided during the crucial early years of his career, offers a captivating journey through the evolution of his architectural vision. The neighborhood is renowned for hosting the largest collection of Wright's work. Built between 1892 and 1909, your stroll through the neighborhood takes you to several private homes and Wright’s studio providing a fascinating glimpse into his creative progression and the birth of the iconic Prairie style. View the exteriors of nearly a dozen of Wright’s structures. This one-hour walking tour covers nearly a dozen homes on Chicago and Forest avenues and on Elizabeth Court.

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.

Discover one of the Windy City’s most spooky, gruesome destinations when you book advance tickets to the Medieval Torture Museum. Perfect for Halloween—or any other creepy-crawly occasion—this museum includes a wealth of information about medieval torture practices and devices, plus realistic models to add a macabre edge. Book tickets before you travel for a seamless visiting experience, and make use of an audio guide and included ghost-hunting app.

Travel through architectural history on this express, small-group walking tour, which covers Chicago's most famous buildings in chronological order (and which is speedy enough to cater to the most time-pressed travelers). With a guide in the lead, there's no need to fuss over maps or worry about directions. Simply stroll along and listen to the in-depth commentary on Chicago's architectural history; you'll learn about each building, and will have plenty of chances to stop for photos.