Top Chicago Historical Tours - page 3

Chicago Museum of Contemporary Art: General Admission Ticket

3.5

(92)

1 to 3 hoursFree Cancellation

from $22

Head to one of Chicago’s top neighborhoods for food lovers—and try donuts from four of the Windy City’s top specialty bakeries—on this indulgent walking tour. Meet your guide at the Chicago French Market in the morning, and come hungry: you’ll enjoy four different donuts, each representing different culinary styles and traditions. As you go, wander the West Loop and Restaurant Row, and learn more about Chicago’s dining scene.

Delicious Donuts & Sweet Treats: West Loop Walking Tour

(62)

1 hour 30 minutes to 2 hoursFree Cancellation

from $70

Enjoy an active and entertaining way to explore Chicago’s highlights with this small-group Segway tour. Meet your guide at a convenient location in downtown Chicago, get acquainted with your Segway before setting off, and then hit the road. You’ll discover top Windy City highlights, including Millennium Park, the Buckingham Fountain, the Museum Campus, and more, all while learning about the city’s history and insider facts from your guide.

2-Hour Guided Segway Tour of Chicago

4.7

(496)

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

from $65

Likely to Sell Out

Chicago City Tour with Architecture River Cruise Option

4.8

(716)

2 to 4 hoursFree Cancellation

from $50

Lincoln Park Hauntings Ghost Investigation Tour

(45)

2 hours 15 minutesFree Cancellation

from $40

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once seemed as though the stunning architectural details of Chicago's Old Post Office would be lost to time while the building sat vacant for almost two decades. But the 2.8 million square foot building, completed in 1934, recently went through a monumental renovation and now serves as a modern multi-use event and office space that meets today's need for large, light-filled workspaces. See how historic artifacts and building details have been creatively incorporated into the Old Post Office's design including the conversion of the roof to a 3.5-acre urban rooftop park. Old places can become new spaces when a developer with vision collaborates with an award-winning architectural team.

Explore the Historic Old Post Office in Chicago

(20)

Let’s take photos at one of Chicago’s most famous spots - the bright red CHICAGO sign at the Chicago Theatre! During this 30-40 minute photo walk, I’ll help you pose and feel comfortable while taking high-quality photos using iPhone, optimized for social media. You’ll receive about 50 digital photos, including 5 professionally color-edited images, delivered via a private online gallery. Please download your photos within 14 days after receiving access, as the gallery link will expire.

from $15

Express Chicago Photo Tour of Landmarks

(4)

30 to 40 minutesFree Cancellation

from $99

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!

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

3.9

(2,233)

from $49

Likely to Sell Out

Chicago Murder Mystery Tour

(734)

This is not a bus tour, 90% of our tours are 11 people or less, as we specialize in small, personalized group tours. This gives us the space and time to take pictures and have great conversation! The personal, small tour approach allows travelers to have a personal tour experience of the city. With our small tour there are opportunities for questions and non-scripted conversations. A true experience. We have additional tours that accommodate large groups but this tour is geared towards sights and fluid conversations about the black starts of Chicago! The guide will take photos for you while educating you on the city and it's historical residents. On the Chicago Soul House tour, travelers tour the South Side of Chicago and can see the homes of the city's stars. The antidotes and stories are being told by someone who sang at the same lounges as Jennifer Hudson, played with Muhammad Ali as a child and traveled to Chicago during the Great Black Migration.

from $35

Likely to Sell Out

2 Hour Private Chicago Soul House Tour

3.8

(4)

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.

from $65

Chicago Food and Culture Walking Tour

4.6

(17)

Discover the heart of Chicago’s Chinatown with your authentic history and culture tours, exclusively offered by the official Chinatown Visitor Center. Led by experienced local guides, your tours dives deep into the neighborhood’s rich heritage, hidden landmarks, and cultural traditions. Unlike generic tours, we bring you behind the scenes with insider stories, community connections, and exclusive access to local favorites. Experience Chinatown through the eyes of those who know it best. A minimum of 2 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.

from $39

2-Hour Chicago's Chinatown History and Culture Tour

3.8

(5)

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

from $30

Lake Michigan Skyline Cruise in Chicago

4.4

(906)

30 to 45 minutesFree Cancellation

from $33

Delve into the rich history and notable architecture of one of Chicago’s most luxurious neighborhoods—and learn insider stories as you go—with this self-led smartphone audio walking tour. Upon booking, download the app and set off at a time and pace that work best for you. You’ll discover Gold Coast landmarks from historic piano bars to the original Playboy Mansion, and can stop and start the tour whenever you like.

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

4.3

(7)

50 minutes

from $8

Embark on an interactive adventure through Chicago’s Chinatown with the Dragon Kings Quest, a mobile escape game blending urban exploration, riddles, and local legends. Use your phone and the Questo app to follow clever clues, unlock stories, and discover must-see landmarks from Chinatown Square and colorful murals to hidden gems and Ping Tom Memorial Park. Go at your own pace, play solo or with friends, and experience the city in a totally new way. Fun for all ages—perfect for families, date nights, or teams seeking a unique outdoor challenge!

Chicago Chinatown: Dragon Kings Puzzle Adventure

4.1

(9)

48 minutes to 1 hour 18 minutesFree Cancellation

from $8

Price varies by group size

There’s so much amazing architecture in Chicago but wandering around alone can leave you overwhelmed, and unsure of what you’re looking at. Check out some of Chicago's most important new buildings on an architecture walking tour. The tour is focused on the area around the Chicago Architecture Center (CAC), beside the Chicago River, so you don’t get overwhelmed exploring the whole city. Admission to the CAC’s galleries is also included.

Chicago Architecture Walking Tour: What's New

(82)

Chicago is renowned for its wealth of spectacular architecture—and this small-group tour gives you the special chance to discover building interiors that most visitors overlook. In the afternoon, meet your guide in Downtown Chicago, and get ready to discover the interiors of five of the city’s most striking art deco skyscrapers. As you go, soak up the skyline views, and learn more about the city’s unique architectural history.

from $35

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

(89)

Leave behind the stuffy, slow-moving tour groups and explore Chicago’s Millennium Park on your own with a private, self-guided app tour. Using just your smartphone, pausing as you like, you’ll learn all about “The Bean,” Lurie Garden, Crown Fountain, and more. With your GPS cuing your audio experience, this tour lets you go at your pace, style, and time, with lifetime access and no expiry.

from $35

Chicago Millennium Park Self-Guided Walking Tour

4.6

(5)

1 to 2 hoursFree Cancellation

from $15

3.9

(356)

Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO

1 to 30 daysFree Cancellation

from $84

4.6

(145)

Lakefront Segway Tour in Chicago

Chicago Architecture Center Exhibits Admission

from $70

4.4

(76)

45 minutes to 1 hourFree Cancellation

from $7

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.

Chicago Self-Guided Audio Tour

3.9

(9)

3 to 9 hours

from $6

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

(213)

Leave behind Chicago’s buzz and see the Windy City as it used to be, some 150 years ago. The Oldtown Triangle—one of the most beloved ‘hoods in the city—survived the Great Chicago Fire of 1871, and it still stands today as a beacon to history. With your guide at the helm, you’ll witness fantastic architecture, national landmarks, and hear stories of the city’s often wild past.

from $35

Workers Cottages of Oldtown Triangle Walking Tour

(50)

1 hour 45 minutes

from $45

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What are people saying about Chicago

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

Stephanie_S, May 2026

A Wonderful Afternoon at the Art Institute

Sergio was our art expert. The experience was memorable. There were so many pieces I had walked past so many times before and now I will never walk past again without stopping and taking them in. I can’t wait to take his tour again. I will never go to the Art Institute without a tour again. There is so much to learn and so little time. Sergio has a strong presence and it was evident he was one of the top guides at the museum. I learned so much in 2.5 hours.

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 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.

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 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.