Top Chicago Historical Tours

Original Chicago Architecture Interiors Tour: Dazzling Interiors

(1,580)

Chicago Crime and Mob Bus Tour

from $35

4.6

(3,280)

1 hour 30 minutes to 2 hoursFree Cancellation

from $49

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Chicago River 90-Minute Architecture Tour

4.7

(9,859)

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.

from $45

Total Chicago: From Architecture to Food

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

(1,204)

4 hours 30 minutesFree Cancellation

from $91

Price varies by group size

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

(141)

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.

from $35

Field Museum of Natural History Admission Tickets

4.6

(511)

4 hoursFree Cancellation

from $29

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

(421)

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.

from $35

Chicago City Minibus Tour

(550)

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.

from $50

Chicago's Original Gangster Tour by Bus

4.7

(127)

1 hour 45 minutesFree Cancellation

from $48

Likely to Sell Out

Join us in the daytime or evening for City lights and breathtaking views

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.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

4.7

(3,125)

45 minutesFree Cancellation

from $28

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

4.8

(15,967)

1 hour to 1 hour 30 minutesFree Cancellation

from $39

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

(255)

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.

from $47

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

(285)

2 hours 30 minutesFree Cancellation

from $90

Price varies by group size

The Chicago Loop is the city's epicenter of culture, commerce, and design.

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers and hidden architectural gems, allowing you to explore at your own pace. Uncover the rich history from the Great Fire of 1871 to the architectural masterpieces that define the skyline. Stroll past renowned theaters, museums, and captivating public art pieces that contribute to the city’s creative spirit. The Loop offers a unique perspective on Chicago's past and present, whether it's your first visit or a familiar stroll. — Self-guided exploration of Chicago’s historic Loop area — Learn about the city’s architectural innovations and history — Visit iconic landmarks like the Art Institute and Millennium Park — Perfect for first-time visitors or seasoned Chicagoans alike

Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

(3)

2 hours to 2 hours 30 minutesFree Cancellation

from $10

4.4

(131)

African American Heritage Tour of Chicago

4 hoursFree Cancellation

from $125

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.

Chicago Architecture Center River Cruise aboard First Lady

(5,707)

1 hour 30 minutes

from $57

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

4.0

(54)

1 hour to 1 hour 15 minutes

from $30

Chicago Walking Tour: Must-See Chicago

(143)

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.

from $35

Field Museum of Natural History Early Access Ticket

4.5

(55)

2 to 4 hoursFree Cancellation

from $73

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.

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

(1,020)

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!

from $51

Chicago River Ghost & Dark History Night Cruise

4.0

(109)

Take your architecture spotting off the streets and inside some of the most iconic buildings in Chicago with this unique Art Deco-themed tour. Get up close and personal with the glamorous style of the early 20th century as you delve beyond the downtown facades to explore glorious interior spaces from the 1920s and 1930s, with their ornate brass and marble details, mosaics, stained glass, and other treasures that most architecture tours miss.

from $46

Likely to Sell Out

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

(96)

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.

from $35

2-Hour Chicago Lakefront & Museum Campus Segway Tour

(349)

Considered Chicago’s original “Millionaire’s Row,” Prairie Avenue in the Near South Side is renowned for its Gilded Age mansions—and this tour makes exploring easy (and delightfully spooky). In the evening, meet your guide in front of the Glessner House, and set off with ghost-hunting gear to accompany you. In between spotting highlights including the Marshall Field Jr. Mansion and the Henry B. Clarke House, you’ll hunt for specters and hear ghost stories.

from $70

Special Offer

Tourgoers in front of the Marshall Field Mansion

Prairie Avenue Haunted History Tour and Ghost Hunt

(12)

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

BYOB Spray Paint and Sip at Studio W.I.P.

Alana_M, Apr 2026

Great experience. Do it. Date night, birthdays, creative outlet, just go.

Camile was a great instructor and had such a good vibe. Learned some really helpful techniques from him ( creating text, drip, splatter and overlay/drop shadow) that were easy to incorporate into our work. We also had a minute to practice on the walls. They had canvases prepared and a ton of spray paint colors to share with the group. In addition to that there were a lot of stencils to choose from. I would only say that there needs to be better ventillation. But other than that, it was a great experience and we would definitely do it again!

African American Heritage Tour of Chicago

Sheila_C, Apr 2026

Must Go To Tour

This was one of the best tours my sister and I have ever gone on together. Steve, our tour guide was very knowledgeable, patient and thorough. He explained and showed us things that we did not know about Chicago and it's a must go see. Stop believing how TV shows depict Chicago, especially the South Side. The BRONZEVILLE homes are absolutely beautiful. Its a great tour for all ethnicities to see. It was eye opening for sure. Steve gave us plenty of time to take pictures, ask questions, and to eat a great meal. The visit to the museum was great also.

Field Museum of Natural History Early Access Ticket

Jim_C, Apr 2026

Well Worth the Price

As museum people, we jumped on this opportunity for an early access tour. There were only two other people on our tour and all of us showed up 15 minutes early so no time was lost waiting for the temporally challenged. Our guide, Mariah, was friendly, charming, and very knowledgeable. She guided through the museum, supplemented the exhibits, and answered all our questions. It was especially nice to see Sue, the T-rex. Without the crowds. After the tour, which coincided with the opening of the museum, we visited other exhibits at the museum. The museum filled quickly, particularly as school groups started to arrive, so we were very happy to have had this early access opportunity, particularly with such an outstanding guide as Mariah.

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

Rebecca_M, Mar 2026

Art Tour Extraordinaire

This was a tour about which songs will be song! Our guide, Spiro, was AMAZING! He was knowledgeable, patient, kind, and engaging…he even extended the tour slightly to make sure we all got to see what we wanted to see within the museum (for me, that was St. George Slaying the Dragon, which was not part of the tour). I love tours, and I have taken them all over the world, and this one ranks amongst the best!

Field Museum of Natural History Admission Tickets

Heather_T, Feb 2026

Highly recommend!

Wow-what an incredible museum! I spent hours exploring! Highly recommend if you’re interested in earth’s history! So much to discover about plants, animals, and people. SUE is extraordinary! The ticket was super easy to purchase and I walked right in upon arrival. Overall, a fantastic experience!

Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

Sandra_L, Feb 2026

Recommended highly!

This was an enjoyable, educational experience. Samantha was knowledgable and could answer any question asked of her. We have been to the museum many times, but wanted a deeper understanding than we could obtain from reading the plaque by a picture. Samantha provided that insight. Thank you for a great morning at the museum!

Haunted Chicago Booze and Boos Ghost Walking Tour

Tammy_B, Oct 2025

Mother daughter night in Chicago

Bobby Thomas was our guide. Although new to Chicago, he was very knowledgeable in history. We enjoyed hearing the stories, and the drinks along the way were a fun bonus. We all enjoyed each other’s company so much that we went to eat together afterward, including our guide! Highly recommend!

Chicago's Original Gangster Tour by Bus

MARIADOLORES_L, Aug 2025

Comfortable fun tour

The tour guide was knowledgeable and funny. I thought we would get out of the vehicle to explore some sites but as it turns out through no fault of the company, many of the sites are not there anymore or they are privately owned businesses that you couldn't go into anyway. Still the tour was very interesting, and again the tour guide was fun

Chicago Landmarks & Museum Campus Small Group Segway Tour

WaiWen_C, Jun 2025

Great Segway Tour seeing Chicago!

We were visiting from Philadelphia，and Celest was our guide. She was energetic, informative and knowledgeable regarding the city and the sights. She was adamant about safety, and gave us a great lesson on how to ride the Segway, and what to look out for while we were sight seeing. My family and I had a lot of fun, and would recommend this one of a kind tour of the city. It is the BEST way to see it by covering lots of ground more than walking on foot.