Top Chicago Historical Tours - page 2

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Lincoln Park Hauntings Ghost Investigation Tour

2 hours 15 minutesFree Cancellation

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

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.

Chicago Landmarks and Museum Campus Small Group Segway Tour

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

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

Haunted Chicago Booze and Boos Ghost Walking Tour

2 hours 30 minutesFree Cancellation

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

Chicago Loop Self-Guided Audio Tour: Architecture & History Walk

2 hours to 2 hours 30 minutesFree Cancellation

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.

Field Museum of Natural History Early Access Ticket

2 to 4 hoursFree Cancellation

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

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

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

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became a global force in culture, commerce, and architecture. Our tour will explore building interiors like the world's oldest skyscrapers, City Hall, the underground Pedway, and the old library. We will observe public art like the Picasso and the Bean. While immersed in the places where it happened, Chicago's colorful stories will vividly spring to life. This walking tour aims to enhance your understanding of modern-day Chicago by a deep dive exploration of its history. Your guide to the city is the friendly and well-informed Dave Lineal: local artist, culture vulture, and historian. Dave is tested and certified by the Chicago Tour-Guide Professionals Association. This is an outdoors / indoors all-weather walking tour with a duration of two hours. We will meet under the marquee at the Chicago Theater, 175 N. State Street.

History and Architecture of Chicago Loop Walking Tour

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.

Chicago Favorites Ultimate Food and Walking Tour

3 hoursFree Cancellation

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.

360 CHICAGO Observation Deck Admission

1 to 4 hoursFree Cancellation

3.9

(1,314)

from $27

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

Wind and Souls an Adults Only Ghost Tour in Chicago

Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.

Private 45-Minute Chicago Skyline Helicopter Tour

45 minutesFree Cancellation

Learn all about the history beyond one of Chicago’s best-known thoroughfares—and spot numerous architectural icons as you go—on this small-group walking tour of the Magnificent Mile. Meet your guide at the Chicago Architecture Center and set off to soak up the street’s ambiance, and discover highlights like the Wrigley Building, John Hancock Center, and more. Entry to the Chicago Architecture Center is also included, so you can extend the experience.

Chicago Walking Tour: The Magnificent Mile

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).

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

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.

Prairie Avenue Haunted History Tour and Ghost Hunt

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.

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

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.

Special Offer

Chicago Insider Segway Tour

Chicago Lake and River Architecture Tour

Paint your own street art at Studio WIP

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

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.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Catherine_M, Sep 2026

Spencer was the best!

This was a wonderful tour that showed some hidden gems in the city. Our tour guide, Spencer was knowledgeable, enthusiastic and brought the history of Chicago architecture to life. He offered to share recommendations on attractions and dining and gave us his email. True to his word, he promptly answered an email asking for dining recommendations in a specific part of town. I highly recommend this tour.

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.