Top Chicago Historical Tours

Chicago Gangsters and Ghosts Walking Tour

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.

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

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.

Historical and Architectural Chicago Fireboat River & Lake Cruise

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.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

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.

Field Museum of Natural History Admission Tickets

4 hoursFree Cancellation

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

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.

Chicago in a Day Walking Tour: Food, History & Architecture

4 hours 30 minutesFree Cancellation

Price varies by group size

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

African American Heritage Tour of Chicago

4 to 7 hoursFree Cancellation

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.

Chicago City Minibus Tour

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.

Chicago's Original Gangster Tour by Bus

1 hour 45 minutesFree Cancellation

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.

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

2 hours 30 minutesFree Cancellation

Price varies by group size

Chicago Night Crimes Tour by Bus

Stop off the bus at Chicago Landmark Building with Prohibition Era History

2 hours to 2 hours 30 minutesFree Cancellation

Learn about the history and legends surrounding the 1893 Chicago World's Fair and notorious criminal H.H.Holmes on a half-day tour inspired by the popular book ‘The Devil in the White City.’ Explore important locations such as the Prairie Avenue Historic District, Jackson Park, Midway Plaisance Park, and the ‘Murder Castle’ of H.H. Holmes as you learn more about the World's Columbian Exposition and Victorian Chicago.

The Devil in the White City: A Haunting History Tour

3 hoursFree Cancellation

Chicago Murder Mystery Tour

Discover more of Chicago beyond downtown with this convenient South Side open-top shuttle transfer. Travel from central Chicago to some of the city’s most important cultural and historic destinations, including Jackson Park, the Obama Presidential Center campus, and the Griffin Museum of Science & Industry. Enjoy an easy ride south without arranging taxis, rideshares, or public transit connections. The shuttle first stops near the Obama Presidential Center and Jackson Park, giving you access to one of Chicago’s most historic lakefront spaces. Explore the area at your own pace, take photos, or continue your visit independently. The route also serves the Griffin Museum of Science & Industry, one of Chicago’s most popular attractions and one of the largest science museums in the world. This is a great option for travelers who want a simple, affordable way to visit Chicago’s South Side highlights from downtown. Choose a one-way transfer or an all-day ticket for added flexibility.

Roundtrip Shuttle to South Side and Obama Presidential Center

30 minutesFree Cancellation

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.

Chicago Walking Tour: A Walk Through Time

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.

2-Hour Chicago Lakefront & Museum Campus Segway 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 hidden spaces, from Frank Lloyd Wright’s sunlit masterpiece inside the Rookery to the world's largest Tiffany stained-glass domes at the Cultural Center and Marshall Field Building. Walk through the stunning Gilded Age luxury of the Palmer House and iconic movie backdrops along La Salle Street at a relaxed, conversational pace. We combine world-class history with photo vantage points, ending with personalized local recommendations. Don’t just see Chicago, experience it from the inside out.

Chicago's Secret Interiors Architectural Walking Tour

Chicago Walking Tour: Must-See Chicago

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!

Chicago River Ghost & Dark History Night Cruise

Immerse yourself in American literary traditions, and enjoy a wide range of interactive exhibitions, during a visit to Chicago’s one-of-a-kind American Writers Museum. Conveniently located on Michigan Avenue, the museum was established in 2017, and is one of the city’s newest highlight institutions. Guarantee your admission, and prevent any travel hassles, by securing your tickets in advance. Once inside, you’ll have time to explore at your own pace.

American Writers Museum Admission Ticket

1 to 5 hoursFree Cancellation

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s most influential neighborhoods. Guests will enjoy curated tastings from locally owned Black restaurants while learning about the people, businesses, and historical moments that helped shape Chicago’s Black cultural landscape. Along the route, we visit significant landmarks, including the site where Barack and Michelle Obama’s love story began, historic community gathering spaces, public art, and locations connected to the neighborhood’s rich legacy of entrepreneurship, music, education, and civil rights. Unlike traditional food tours that focus primarily on dining, this experience connects each tasting to the larger story of the community, providing travelers with insider knowledge and meaningful cultural context.

Explore Chicago Black Culinary Heritage

2 hours 45 minutesFree Cancellation

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Paint your own street art at Studio WIP

Mikaela_R, Sep 2026

Awesome Experience, totally recommend!

It was great! You could tell he was passionate about what he does and was also very good. It was cool to know he also makes majority of the stencils himself too. Fantastic experience, loved the freedom and wide variety of options with stencils as well. We both finished our canvas happy with the finished product! We also took the red line from downtown to the studio and back.

Chicago's Secret Interiors Architectural Walking Tour

Linda_N, Sep 2026

Architectural Splendor in Chicago

Architectural interiors in the Loop were wonderful works of art. Our tour guide was Annie - very knowlegable about the buildings we visited plus told some interesting side stories. She also gave us some tips about a neighborhood and museum that we were visiting the next day. Well worth your time.

African American Heritage Tour of Chicago

Antonette_J, Aug 2026

Must Book this tour!!!! You get more than you expect!!!!

This tour is a must if you’re in Chicago. Steve was an amazing guide knowledgeable and entertaining.. not a dull moment. If you’re reading this you have to book now and if you get Steve please give him an extra tip for me.. I didn’t have enough cash to show my true appreciation. Priceless..Also Good reviews are a bonus.

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

Jodie_B, Aug 2026

Informative, speedy way to view the key pieces.

We know a little about art, so it was helpful to enter the gallery before opening time (you notice the crowds, once it is open to the public) and have Megan guide us to the pictures you should see if on limited time. 2 to 2 1/2 hours is probably the amount of time you need before you decide you have had enough.

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Ramin_P, Aug 2026

Relaxed and Great Fun. Incredible sense of freedom.

Michael took very good care of us and was very accommodating on our arrival. Segway lesson was fun and clearly explained. Michael’s tour of Chicago was just right - funny, informative, not too much, not too little. The sense of freedom and ease of movement on the Segways was perfect for a big spacious cityscape - our group of . It seemed pricey at first but we were happy that we had had a good experience and it was well worth it. We would do it again - maybe trying one of the other tours they offer (ours was the Museum Campus). A really good way to see the city.

Private 45-Minute Chicago Skyline Helicopter Tour

Jayme_K, Jul 2026

Great View

What an incredible experience! The helicopter ride gave us breathtaking views of the Chicago skyline, Lake Michigan, and all the iconic landmarks. The staff was friendly, professional, and made us feel safe from start to finish. It was smooth, exciting, and definitely one of the highlights of our trip. Highly recommend to anyone looking for a unique way to see Chicago!

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

Lucy_E, Jul 2026

Art Institute tour

This is an amazing art museum - one of the best in the world. And Amanda is a skilled tour guide, helpfully pointing out benches and clearly describing the history of the art pieces we were enjoying. She asked what people were interested in seeing before starting and tailored her tour from there. She is clearly very knowledgeable.

Haunted Chicago Booze and Boos Ghost Walking Tour

Elena_H, Jun 2026

The last bar made me a believer

The whole trip was fun and educational. You need the stomach to handle some tragic gruesome stories about Chicago history, but I enjoyed it. I was agnostic about ghosts until the last bar, which made my friends and I itchy and nauseous with its seriously creepy vibe. The host was passionate and friendly and kept things moving at a great pace.

Chicago's Original Gangster Tour by Bus

DulceMaria_D, May 2026

So gangsta! ⭐️⭐️⭐️⭐️⭐️

Honestly, this exceeded my expectations. I’m a Chicagoan and it felt like I experienced a visit to my own city. It was two hours of “wow” with orchestrated 1920’s music evolving into blues..it was amazing. I recommend and appreciate people like our guide who obviously value our city’s richest history. This was more than a gangsta historical tour, you learn a lot more about origins and impacts. I left being a little extra proud of our city. Thank you! 🎩💐

Field Museum of Natural History Admission Tickets

Julie_C, Mar 2026

Too Much for 1 Day

There is so much to see and explore. Get rest before coming and go see the things you’re interested in first. There is so much to see and experience that it can’t be done in a single day. My kids have very different tastes and we split up. There was something of intense interest for both.

Small Group Tour of Chicago Neighborhoods: North and South Side

Allison_O, Sep 2025

Excellent overview of Chicago

Steve will take you on a comprehensive tour of the area around downtown Chicago and surrounding neighborhoods-we covered about 100 blocks over 5+ hours. I did not find any other tours of the area and would never have found all these sights on my own - it may seem a bit expensive but is truly worth it as you will see so much with a local character providing history and perspective. Steve is a real character and very amusing- and definitely knows his city. We did have some hiccups- he was not aware we had reservations for the tour but as soon as I called him he came to pick us up. So I recommended that you call him to confirm at the number listed on the reservation! (And I agree with prior comments about the driving -a little erratic at time's but on observing other drivers it may just be Chicago drivers ). I definitely recommend this tour if you want a good overview of Chicago!