Top Chicago Historical Tours

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.

(271)

from $35

Original Chicago Architecture Interiors Tour: Dazzling Interiors

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.

(1,711)

from $35

Field Museum of Natural History Admission Tickets

4 hoursFree Cancellation

4.6

(545)

from $29

Historical and Architectural Chicago Fireboat River & Lake Cruise

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

(371)

from $47

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.

Explore Chicago's legendary architecture and history.

Chicago River 90-Minute Architecture Tour

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!

4.7

(10,383)

from $45

Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night Cruise

Vito's Vault Chicago Speakeasy Dinner Theatre

4.1

(147)

from $46

3 hoursFree Cancellation

Price varies by group size

(29)

from $88

Chicago Walking Tour: Historic Treasures of Chicago

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

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.

(433)

from $35

Chicago's Original Gangster Tour by Bus

1 hour 45 minutesFree Cancellation

4.6

(153)

from $48

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum, free time at the Milwaukee Public Market, and an optional Miller Brewery tour and tasting. Enjoy scenic views along the lakefront and an outside visit to the Milwaukee Art Museum before returning to Chicago. Ideal for travelers looking for a relaxed, well-rounded introduction to Milwaukee.

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

8 to 10 hoursFree Cancellation

4.3

(9)

from $125

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

4.3

(1,861)

from $44

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.

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

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

2 hours 30 minutesFree Cancellation

Price varies by group size

(316)

from $90

Total Chicago: From Architecture to Food

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

(1,299)

from $101

Discover one of downtown Chicago's highlight museums, and explore the works of leading artists across myriad media and genres, when you book tickets to the Museum of Contemporary Art. Choose from multiple entry times throughout the day, make your own way to the museum, and get ready to explore. Exhibitions are ever-changing, but you can expect to see works by artists the likes of Kara Walker, Jasper Johns, Cindy Sherman, and beyond.

Chicago Museum of Contemporary Art: General Admission Ticket

1 to 3 hoursFree Cancellation

3.5

(92)

from $22

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

1 hour to 1 hour 15 minutes

4.0

(56)

from $32

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

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.

3.9

(2,312)

from $49

Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

Experience Chicago in a new way on this small-group Segway tour. Visit Chicago’s "front yard," and see more of the sights in less time. Glide along the fragrant floral paths of Grant Park to the famous Buckingham Fountain. Then, travel along the banks of Lake Michigan to the Museum Campus for top-notch views of the city’s iconic skyline. Guided Segway training and helmets are included, making this a beginner-friendly tour.

(6,336)

from $57

Chicago Landmarks & Museum Campus Small Group Segway Tour

(235)

from $70

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

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.

(610)

from $50

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,478)

from $39

Immerse yourself in the pizza culture of Chicago on this hearty lunch tour. Enjoy deep dish—and then go beyond it, with commentary from your food-loving guide and tastes of four different pizza varieties. Learn all about Chicago's history and culinary heritage as you go, and receive an introduction to the city's pizza scene that's more in depth than what other tours offer, with lunch included.

Chicago West Loop Pizza Crawl

3 hours

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.

(8)

from $79

Tourgoers in front of the Marshall Field Mansion

Prairie Avenue Haunted History Tour and Ghost Hunt

2 hours 20 minutes

Our goal is to disturb and unsettle you of whatever assumptions you may have about Chicago. We do so with our entertaining and brilliantly researched experiences, that highlight the historic gangster past of Chicago, and also shares the hidden beauty, natural wonders, and cultural highlights of America's third-biggest city. Guests walk away more historically oriented travelers, with a reason to visit Chicago again.

(12)

from $40

Chicago True Crime and Gangsters Tour

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

(8)

from $35

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Glenn_F, Jul 2026

Samantha P is wonderful tour guide

Samantha P was an outstanding tour guide for our Art Institute Tour. My wife took a lot of art history in college and was impressed by Samantha P knowledge while I know nothing about art but found her description and context of the artwork very understandable.

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Josephine_M, Jun 2026

Perfect way to see Chicago!

We had such a great time- Tammy was our guide and she emphasized all the safety planning, eased us into riding and was incredibly patient during our ride! She was also a complete hoot - even my grumpy teenager was laughing and having fun! Thanks Tammy!!

Chicago Walking Tour: Historic Treasures of Chicago

Laura_O, Jun 2026

Chicago Architecture Walking tour with Bill

After already doing the architecture tour by boat, I wanted to spend more time getting up and close with the buildings. Bill was a fantastic tour guide who shared so much knowledge and history about some of Chicago's most fascinating buildings. It was like a behind the scenes tour of Chicago that many visitors never experience. I learned so much about the cultural center and Tiffany's domes. Would highly recommend. Your ticket includes entry to the Chicago Architecture Museum, so we checked that out after the tour too.

African American Heritage Tour of Chicago

Deniece_C, May 2026

Love for Southside

I thoroughly enjoyed learning about the rich history of the Southside of Chicago. Steve is very knowledgeable and gave a wonderful history lesson about the remarkable black people who triumphed through immense adversity and made their mark on Chicago and beyond. It was heartwarming to stand in front of the residence where these beautiful people once resided.

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

Therese_M, May 2026

Art Institute Highlights Tour

The tour of the Art Institute we took with Samantha P. was excellent. We had the opportunity to see as many highlights as time permitted. Samantha was very knowledge and open to the many questions we asked. I would definitely recommend this tour & Samanatha in particular.

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!

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.

Chicago's Original Gangster Tour by Bus

Ann_S, Oct 2025

What an adventure!

Marie was great. We enjoyed the tour very much. She was informative and funny. Very impressive. We were visiting from Arizona and when friends gave me the list of tours this one caught my attention as my parents were born in that era and my dad was an Indiana State trooper in the 40’s. I will recommend this adventure to anyone I know is visiting Chicago.

Vito's Vault Chicago Speakeasy Dinner Theatre

Stephen_L, Oct 2025

Join Vito and the Gang for a great night... Just don't forget the password😉

Absolutely brilliant evening! Vito and the team put on a fantastic night. A small, intimate speakeasy-style bar and restaurant with stunning 1920s-inspired décor. Dinner was delicious, and the service was excellent. The show was outstanding — a perfect mix of amazing singing, lively dancing, and plenty of laughs! Huge thanks to Vito and the team for such a wonderful experience that we both thoroughly enjoyed. Just don’t forget the password 😉 Stephen 🇬🇧