Top Chicago Historical Tours - page 5

2 Hour Bronzeville, Chicago Tour

Private Wicker Park and Bucktown Walking Tour

from $45

2 hours 30 minutesFree Cancellation

If you want culture, history, food, cinema and film and a heavy dose of all things Chicago this is your tour! Get ready to EAT. We are true fans of Chicago, The Bear and good food which is why we start our tour at the world famous Pequod's pizza where a hot pie will be ready waiting for us to pickup and try. Enjoy this in the pedicab as we begin our leisurely ride through the city getting an open air view of some of Chicago's cutest neighborhoods. Next up we go to Margies Candies for a Banana Split before embarking on a ride all the way from the west side to River North, crossing the Chicago River and getting some photos at the iconic LaSalle Flowers. End your epic Chicago adventure at Mr. Beef or Kasama! Your tour vehicle will be a decorated 6 seat pedicab driven by one of our knowledgeable tour guides. Comfortable for up to 4-5 adults, 6 if kids/teenagers are in the mix. Look at the photos of the cab and feel free to reach out with any questions.

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from $195

Per group

The end of our tour, and the start of The Bear, Mr Beef!

The Bear Private Pedicab Food Tour of Chicago

2 to 3 hoursFree Cancellation

from $200

Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant city at your own pace. Begin at Millennium Park where Anish Kapoor's Cloud Gate reflects the skyline that pioneered skyscraper design and continues to push architectural boundaries today. Wander along the Chicago Riverwalk where boat tours explain how the city reversed the river's flow and rebuilt in steel and stone after the Great Fire of 1871. Marvel at the ICAs world-class collection. Explore the Magnificent Mile's shopping and historic Water Tower, then discover the vibrant neighborhoods where Polish, Mexican, and African American communities have shaped Chicago's culture. Experience the blues at clubs where Muddy Waters and Buddy Guy defined a genre, then savor deep-dish pizza in the taverns that perfected this Chicago original.

Discover Chicago: A Self-Guided Walking Tour

Discover Chicago: A Self-Guided Walking Tour

8 hours 30 minutesFree Cancellation

2.0

Looking for a convenient way to see Chicago rain or shine? Discover Chicago and its remarkable landmarks in a unique way with a private tour designed just for you. Enjoy the comfort of a private car as a friendly local guide takes you through the city’s iconic architecture, vibrant neighborhoods, and scenic drives. This tour allows you to explore at your own pace while receiving insider tips and local insights. - Private tour for 1-3 people with a local guide - Explore iconic landmarks and vibrant neighborhoods - Flexible itinerary tailored to your interests - Enjoy the comfort of a private car with scenic drives

from

Personalized Private Driving Tour of Chicago for 1-3 People

Personalized Private Driving Tour of Chicago for 1-3 People

from $395

Discover the rich history and architecture of downtown Chicago with local expert Dave Lineal. Walking underneath the soaring buildings, we will learn how Chicago grew to become a global force in culture, commerce, and architecture. How did this roaring city come to be? We will hear the tales of Chicago history immersed in the places where it happened -- exploring historic building interiors like the world's oldest skyscrapers, City Hall, and the old library. This deep dive in city history and architecture aims to deepen our appreciation of what Chicago is today.

History and Architecture of Chicago Loop Walking Tour

Explore the best of the Great Lakes region on this four-day tour departing from Chicago. Travel through lakeside cities like Milwaukee, Green Bay, and Traverse City, discover national parks and stunning beaches, and visit the iconic Mackinac Island—ranked among the world’s most beautiful islands. Guided by local experts, you’ll enjoy scenic walks, museum visits, and the region’s natural wonders with comfortable transport and included breakfasts. This well-paced trip gives nature lovers and explorers the ultimate lakeshore adventure across Superior, Huron, and Michigan.

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from $30

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

4 daysFree Cancellation

from $1,125

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary flavors with its most iconic landmarks. Savor Chicago Pizza, Hot Dogs, Italian Beef, Garrett’s Chicago Mix Popcorn, and the original Palmer House Brownie, or elevate your day with our VIP craft beer upgrade. This unforgettable Chicago in a Day Tour explores Millennium Park, the Chicago Riverwalk, Michigan Avenue, Cloud Gate, Chicago Theater, and more, guided by true local experts. Enjoy a 5-hour journey through culture and cuisine, plus a FREE 2-hour bike or kayak rental to continue the adventure along Lake Michigan. Recently honored among the “Top 10 Food Tours in America” (USA Today) and “Top 20 Food Tours in the World” (TripAdvisor), this award-winning Culinary Tour is one of the top Things to do in Chicago. Don’t miss the most delicious, scenic Full Day Food Tour in Chicago—all in one extraordinary day.

Likely to Sell Out

A Chicago hot dog loaded with bold, colorful toppings is one of the tastiest Things to do in Chicago. Our Chicago Food Tours feature this classic bite, making Food Tours in Chicago unforgettable.

Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

5 hoursFree Cancellation

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects modern civic expression. What defines Chicago’s identity as a center of American innovation? Cloud Gate offers a striking reflection of skyline and sky. The DuSable Bridge stands as an engineering achievement tied to the city’s growth. Along the waterfront, Navy Pier reveals Chicago’s connection to commerce and recreation. This route connects cultural landmarks with the story of a city shaped by industry and design. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

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from $99

Private Cultural Walking Tour in Chicago with Lakefront Landmarks

Private Cultural Walking Tour in Chicago with Lakefront Landmarks

from $869

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians who made up what was known as the “Chicago Outfit” • Hear from producer Richard Junger, an urban historian, professor and author passionate about Chicago • Do it all in 45 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code. The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

45 minutes to 1 hour

3.0

from $7

Step into the shadows of Chicago’s past on this adults-only haunted pub crawl, where ghost stories, historic landmarks, and legendary nightlife collide. Beginning near the iconic Palmolive Building, this guided experience takes you through the city’s Gold Coast and beyond, uncovering the eerie aftermath of the Great Chicago Fire and the restless spirits it may have left behind. Along the way, you’ll visit a curated mix of historic sites and local bars, blending chilling storytelling with time to grab a drink and soak in the atmosphere. Adults 21+ only, must have valid I.D.

Burning Spirits Haunted Pub Crawl

from $35

Roam the lively heart of Lincoln Square with its cafés, delis, and other fun and fascinating stores; stand beside the Berlin Wall; take in ghastly history, gorgeous murals, and 300-year-old oak trees; and, at your journey’s end, find yourself rewarded by the sight of an architectural gem. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. Join the game! Highlights include: • Explore Merz Apothecary, Gene's Sausage Shop and Delicatessen, Lincoln Square Mural and lesser-known places. • Enjoy a uniquely crafted story brought to you by our top-notch/gifted/talented writers. • Try a new type of experience, the perfect mix between a tour, outdoor escape game, and treasure hunt. After your booking you will receive an email with instructions on how to download and play the game on your phone. We recommend that each user purchases a ticket for an optimal experience, although several people can share a phone.

Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago

Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago

1 hour 50 minutes to 2 hours 20 minutesFree Cancellation

3.3

(3)

from

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

Chicago Chinatown: Dragon Kings Puzzle Adventure

48 minutes to 1 hour 18 minutesFree Cancellation

3.8

(10)

from

For sightseers looking to put a spooky spin on their night and avoid the overpacked city tours that tell history most of us already know, this Chicago Family-Friendly Ghost Tour is just the thing. Stop at popular Chicago attractions, including the Flying Dragon sculpture, the Chicago Stock Exchange Arch, the Abraham Lincoln statue, and Buckingham Fountain, while a guide tells you ghost stories along the way.

Haunted Chicago: Lincoln Park Ghost & History Walking Tour

Haunted Chicago: Lincoln Park Ghost & History Walking Tour

1 hour 30 minutesFree Cancellation

4.1

(12)

from $30

Chicago Haunts and Hooligans Tour

1 hour 30 minutesFree Cancellation

Enjoy a flexible way to explore Chicago—and combine your sightseeing with a fun-filled scavenger hunt game—with this two-in-one smartphone excursion. Upon booking, receive access to the game on your smartphone, and set off at a time that works best for you. In between admiring highlights like the Chicago History Museum, Standing Lincoln Monument, and Lincoln Park Zoo, you’ll solve clues and participate in challenges.

Haunted Chicago: Lincoln Park Ghost Escape Game

4.0

(6)

from $8

Hanfu Chinese Traditional Costume Try on

1 dayFree Cancellation

Illinois Holocaust Museum Experience360 Admission

from $20

1 to 2 hoursFree Cancellation

Uncover the essence of Chicago's sports culture on this guided tour through the downtown area. Learn about the city’s iconic sports figures, explore fascinating stories, and discover the hidden sports landmarks that define the lives of Chicago fans. This tour offers a unique perspective on how sports are woven into the fabric of the city, providing insights that only a local guide can share. Whether you're a die-hard sports fan or just curious about the city's history, this tour is perfect for anyone looking to delve deeper into Chicago's athletic legacy. - App-Guided tour focusing on Chicago's rich sports history - Explore the downtown area and discover hidden sports icons - Learn about legendary figures and their impact on the city - Ideal for sports enthusiasts and those interested in local culture - Opportunities to purchase Chicago sports-related souvenirs

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from $12

Chicago Downtown Sports History Adventure

Chicago Downtown Sports History Adventure

from $5

We wrote the book(s) on Chicago ghosts! Now in our 26th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's haunted history over more than two decades. Chicago Hauntings is the original Chicago ghost tour and still the best. Our tours are based on all original research, unlike the many other knock-off tours you'll find today. Beware of the imitations. Imagine walking in the steps of Chicago's most notorious criminals at the city's original courthouse, putting your fingers into actual bullet holes from Chicago's gangland days, feeling the haunting presences near the site of the old Cook County gallows, and gazing upon the waters where 844 souls lost their lives in the horrific Eastland disaster of 1915. Come along and experience all this and more.

The legendary historic and haunted Tribune Tower

Chicago Hauntings Original Ghost Walk through Old Chicago

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired European styles to bold American Art Deco and Modernist innovations to today’s Contemporary designs that continue to set the pace for world-leading architecture. As you journey through Chicago’s spectacular skyscraper canyons and stunning interiors, you’ll see how economics, technology, creativity, and gritty determination shaped Chicago’s ever-evolving skyline. Whether you’re a visitor or you’re a Chicagoan who has never explored the architectural masterpieces you see every day, join us today on this enlightening adventure.

Intro to Chicago Architecture

1 hour 45 minutesFree Cancellation

Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, including the first Europeans to come through here, the Great Chicago Fire, the origin of the skyscraper, the 1893 World’s Fair, Prohibition and the creation of Millennium Park. Along the way, you’ll discover some of the Loop’s most beautiful interiors, found in buildings that thousands of people walk past every day, completely unaware of what’s inside…And how things created inside those buildings shaped our current world for the better. You’ll hear the stories of the men and women--including Jean Baptiste Point du Sable, Daniel Burnham, Potter and Bertha Palmer, and Muddy Waters--who made Chicago what it is today, and those, like Jeanne Gang, who are defining Chicago’s architectural future.

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from $35

Per group

Chicago Architecture, History and Culture Loop Walking Tour

Chicago Architecture, History and Culture Loop Walking Tour

3 hoursFree Cancellation

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.5 hour small group (12 Guest Maximum) guided walking tour is perfect for busy sidewalks and getting up close to monumental art! Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

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from $50

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

2 hours 30 minutesFree Cancellation

(4)

from $52

Take a time travel journey inside Chicago's best-kept secret: a 125-year-old architectural marvel. This extraordinary building was envisioned by renowned architect Solon Spencer Beman, famous for designing the town of Pullman and the iconic Pullman Palace Car Company. Get ready to be transported through time and history as you explore the legacy of this architectural genius and the fascinating stories hidden within these hallowed walls. Join us for an unforgettable adventure into the past and witness the living testament to Beman's architectural prowess.

Likely to Sell Out

Main doorway to the Fine Arts Building, virtually untouched as designed by Solon Spencer Beman, Circa 1885.

Inside Tour of Chicago’s Fine Arts Building

1 hour to 1 hour 30 minutes

4.9

(26)

from $45

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

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.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

KATHLEEN_M, Jul 2026

Awesome way to spend few hours!!

I live in the Chicagoland area. We just wanted to go to the city and do something different. This tour was awesome. Not too much walking, got to go in a lot of buildings with air-conditioning so the weather was not too much of an issue. We just loved it. Learned so much about buildings that we see every day but I’ve never actually gone into. Highly recommend it for locals as well as out-of-towners. Kate was an awesome guide if you can get her I’d recommend that as well.

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.

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.

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!