Top Chicago Historical Tours - page 2

2-Hour Chicago Lakefront & Museum Campus Segway Tour

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

1 hour 30 minutes

Chicago Night Crimes Tour by Bus

(6,365)

from $57

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

2 hours to 2 hours 30 minutesFree Cancellation

4.8

(503)

from $55

Special Offer

Haunted Chicago Booze and Boos Ghost Walking Tour

2 hours 30 minutesFree Cancellation

Take a deep dive into Chicago's food scene on a small-group walking tour. Head for several of the city's most-notable eateries, including Billy Goat Tavern, known for its "cheezborger," Pizzeria Uno, birthplace of Chicago’s legendary deep-dish pies; and Al’s Beef, a favorite since 1938. Along the way, hear about the friendly rivalry with New York's pizza scene, Chicago's meatpacking roots, 1920s speakeasies, gangsters, and more.

Chicago Food and Culture Walking Tour

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.

4.6

(17)

from $42

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

(1,047)

from $36

The Art Institute of Chicago is home to over 300,000 works of art by local and international artists. With so much to explore, it’s easy to get overwhelmed by all of the options during a visit. Sit back and let an expert guide handle the planning as they take you through the museum’s major pieces. Learn about the history and context behind each piece in this culturally enriching experience.

Art Institute of Chicago Private Expert Guided Tour

Price varies by group size

(107)

from $215

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

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.

4.7

(2,364)

from $45

Chicago True Crime and Gangsters Tour

(8)

from $35

Chicago Murder Mystery Tour

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your interests guide you. Our expertly crafted audio experience unveils exclusive historical insights and hidden stories that even longtime residents don't know, transforming you from tourist to insider as you uncover the authentic soul of the Windy City. Unlike rigid group tours that rush you past remarkable details, you'll have the flexibility to choose which attractions captivate you most, creating a personalized journey that matches your curiosity and schedule perfectly. You'll experience the city as locals do – unhurried, authentic, and deeply connected to the stories that shaped this magnificent metropolis, all while enjoying a superior experience that combines the convenience of independence with the depth of expert knowledge.

(750)

from $35

Chicago Self-Guided Audio Tour

Lincoln Park Hauntings Ghost Investigation Tour

2 hours 15 minutesFree Cancellation

(47)

from $40

Lakefront Segway Tour in Chicago

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

4.6

(146)

from $70

360 CHICAGO Observation Deck Admission

1 to 4 hoursFree Cancellation

3.9

(1,276)

from $30

Enjoy an introduction to Chicago’s highlights and history—on wheels. This small-group Segway tour offers a new, and zippy, way to explore. Meet your guide near Millennium Park, and begin with a personalized training session. Once you’re comfortable on your Segway, explore Millennium Park, roll along the Lakefront, and more. As you go, learn little-known Chicago stories and tidbits, from mafia history to the innovations that changed the city.

Chicago Insider Segway Tour

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on your phone. -Tour at your own pace and schedule -Professionally produced, narrated and musically edited immersive experience -Guided by technology. Put your phone in your pocket as the smart phone tour guided you with voice turn by turn. -Great deal -See and learn about Chicago's haunted spots, tragic events, fires, and the spirits that stayed behind. -Listen again after taking the tour. -The tour never expires, go or listen (after the on location tour) anytime. This haunted adventure is a smart phone guided on location tour. You go to the first stop, open the tour, enter your experience code and press play. From there you are guided turn by turn through Huntsville. The app knows your location and seamlessly guides you each step of the way.

(52)

from $72

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

1 hour to 1 hour 15 minutesFree Cancellation

4.8

(5)

from $10

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks on this scenic lunch cruise along Lake Michigan. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

3.9

(368)

from $63

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!

Chicago Favorites Ultimate Food and Walking Tour

3 hoursFree Cancellation

(2,172)

from $85

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.

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

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

2 hours 30 minutesFree Cancellation

Price varies by group size

(205)

from $90

Feel the presence of the unseen as we wander through haunted history under the moon's glow.

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.

Embers of the Windy City: Chilling Chicago Ghost Tours

1 hourFree Cancellation

4.4

(121)

from $26

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.

Chicago Architectural River Cruise

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

4.7

(840)

from $50

from $144

Chicago Walking Tour: Must-See Chicago

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.

(154)

from $35

Chicago Museum of Contemporary Art: General Admission Ticket

1 to 3 hoursFree Cancellation

3.5

(92)

from $22

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Original Chicago Architecture Interiors Tour: Dazzling Interiors

FENESA_r, Jul 2026

I started this tour with...

I started this tour with a small group, and from our very first stop, I absolutely fell in love. Unfortunately, I had to leave early because I had tickets to the opera, and the show overlapped with the tour. That was completely my mistake, I simply didn't plan my schedule well. Even though I only got to see three of the five buildings, I can honestly say this tour was incredible. I already know I'll be booking it again so I can experience the entire thing. This is one tour you simply have to do. It's fascinating, beautifully put together, and absolutely worth your time. Highly recommend! ✨🏛️❤️

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

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.

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! 🎩💐

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.

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 🇬🇧