Top Chicago Historical Tours - page 3

Private 45-Minute Chicago Skyline Helicopter Tour

45 minutesFree Cancellation

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.

(132)

from $849

Per group

Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

4.3

(1,883)

from $44

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

We invite you to step inside the city’s most exclusive, jaw-dropping architectural treasures. Led by an expert local storyteller, you’ll discover breathtaking hidden spaces, from Frank Lloyd Wright’s sunlit masterpiece inside the Rookery to the world's largest Tiffany stained-glass domes at the Cultural Center and Marshall Field Building. Walk through the stunning Gilded Age luxury of the Palmer House and iconic movie backdrops along La Salle Street at a relaxed, conversational pace. We combine world-class history with photo vantage points, ending with personalized local recommendations. Don’t just see Chicago, experience it from the inside out.

4.7

(846)

from $50

Chicago's Secret Interiors Architectural Walking Tour

Chicago's Secret Interiors Architectural Walking Tour

Chicago Architecture Center Exhibits Admission

(25)

from $35

45 minutes to 1 hourFree Cancellation

4.4

(80)

from $15

Tourgoers in front of the Marshall Field Mansion

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

2 hours 20 minutes

5.0

(12)

from $40

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.

from $144

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

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!

4.3

(19)

from $42

Chicago Hop On Hop Off Open Top Bus Tour

Chicago Hop On Hop Off Open Top Bus Tour

Get to know the “must eats” in Chicago's buzzing Loop District on this small-group or private walking tour. As you explore, listen to in-depth commentary from your guide about the culinary history of Chicago, and get a taste of the city's most iconic foods, from hot dogs to deep-dish pizza. You'll enjoy personalized attention and the chance to chat about your favorite tastings, all while admiring Chicago landmarks along the way.

3.9

(2,362)

from $49

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

Price varies by group size

(124)

from $87

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

(1,294)

from $30

Chicago Walking Tour: Art Deco Skyscrapers Loop

Admire the ornamental facades and intricate interiors of the Windy City's art deco buildings during this in-depth walking tour of the vibrant Loop. This small-group tour will introduce you to some of the city's highlight architectural landmarks and its rich history, all in a single excursion. As you go, get an up-close look at landmarks that many other tours overlook—and learn insider stories from your architecture-expert guide.

Chicago Walking Tour: Art Deco Skyscrapers Loop

Wind and Souls an Adults Only Ghost Tour in Chicago

(190)

from $35

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.

4.2

(46)

from $35

Chicago Architecture River Cruise

1 hour to 1 hour 30 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.

(16,782)

from $39

Chicago Walking Tour: The Magnificent Mile

Chicago Walking Tour: The Magnificent Mile

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.

4.9

(49)

from $35

Chicago Self-Guided Audio Tour

Paint your own street art at Studio WIP

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.

(429)

from $50

Special Offer

Chicago Insider Segway Tour

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

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.

4.9

(100)

from $35

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

8 to 10 hoursFree Cancellation

4.5

(11)

from $125

Chicago Haunted Ghost Tour GPS Self-Guided Walking 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.

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

1 hour to 1 hour 15 minutesFree Cancellation

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

(5)

from $10

1 to 30 days

4.0

(363)

from $84

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Chicago’s “L,” or elevated train, is an icon of public transportation and a major feature of the Loop neighborhood. On this interactive tour, you’ll learn about the railway’s history while experiencing it as a rider. Meet your guide in the morning and set off with just a small group for company. As you ride between stops, you’ll also view Chicago icons like the Willis Tower, and will learn about the city’s architectural history.

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

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.

(99)

from $35

Chicago Museum of Contemporary Art: General Admission Ticket

1 to 3 hoursFree Cancellation

3.5

(94)

from $22

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

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

MARK_P, Aug 2026

Excellent tour with Spiro

Excellent tour with our guide, Spiro. Our small group had all levels of interest and experience - from novice to seasoned, and Spiro expertly led us through the museum with emphasis on the Impressionists. He additionally took the time to address questions and other interests. Seeing the museum with a guide as fun and knowledgeable as Spiro elevated our experience. Highly recommend.

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

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Yolanda_M, Jun 2026

Great tour!

I have been on several segway tours over the years and feel like there are less opportunities to explore cities via segway. Fortunately, my husband and I were guided by Kevin in Chicago. After completing the waiver sheets, helmet fitting and training, we were off. We began our tour near Millennium Park and were able to ride through Grant Park and along the Michigan Lake coast. We were able to see some of Chicago’s highlights while having fun. Kevin was always willing to snap a picture of us too. I recommend it!

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.

Field Museum of Natural History Early Access Ticket

Melissa_d, May 2026

Katie and Sue at the Field Museum

The exclusive tour was a really great experience. I went with my partner and Katie was our tour guide. She was very friendly/helpful. We exchanged tidbits about our interests and goals as the museum is so big. We chose a weekday and there was an event that same day. There weren't any large crowds after our tour ended. Not sure if the day or event was a contributing factor. We got to take photos and videos throughout the exhibits without others in the background. There are some fun interactive spots that I imagine are swamped by children. The best part was seeing Sue! The T-Rex is a must visit. The museum contact on viator was also very helpful as we got lost trying to find our way around the museum. They provide good instructions. If you need an ATM, there's one nearby where the outside food concessions are.

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! 🎩💐

Paint your own street art at Studio WIP

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 🇬🇧

Small-Group Tour of Chicago Neighborhoods: North and South Side

Allison_O, Sep 2025

Excellent overview of Chicago

Steve will take you on a comprehensive tour of the area around downtown Chicago and surrounding neighborhoods-we covered about 100 blocks over 5+ hours. I did not find any other tours of the area and would never have found all these sights on my own - it may seem a bit expensive but is truly worth it as you will see so much with a local character providing history and perspective. Steve is a real character and very amusing- and definitely knows his city. We did have some hiccups- he was not aware we had reservations for the tour but as soon as I called him he came to pick us up. So I recommended that you call him to confirm at the number listed on the reservation! (And I agree with prior comments about the driving -a little erratic at time's but on observing other drivers it may just be Chicago drivers ). I definitely recommend this tour if you want a good overview of Chicago!