Top Chicago Walking Tours

Private Christmas Walking Tour in Chicago with Christkindlmarket

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

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic skyscrapers and stunning lobbies, learning the fascinating stories behind their designs. This 2.5-hour tour is perfect for architecture enthusiasts and curious travelers alike, providing a unique perspective on the birthplace of modern skyscrapers. Whether you’re a local or a visitor, discover why Chicago's skyline is renowned worldwide. - Private tour lasting 2.5 hours, perfect for families and small groups - Visit landmark buildings like The Sullivan Center and The Rookery - Expert local guide shares insider knowledge about architectural history - Flexible meeting points available for your convenience

Private Chicago Loop Architecture Walking Tour

2 hours to 2 hours 30 minutesFree Cancellation

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy to customize the tour itinerary and content for your group. 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.

Private History and Architecture of Chicago Loop Walking Tour

Private History and Architecture of Chicago Loop Walking Tour

2 hours 30 minutesFree Cancellation

Chicago can sometimes feel inaccessible to visitors, but a private walking tour with a local guide takes the mystery out of the city. This personalized tour focuses on the exteriors of iconic monuments, including museums, while your guide shares insights into Chicago’s culture and history. If you wish to explore inside a museum, just let us know in advance and we can create a customized itinerary for you. Perfect for families, solo travelers, or couples, this tour highlights must-see landmarks and hidden gems alike. Connect with the city through local stories, insider knowledge, and expert guidance for an unforgettable experience.

Chicago Custom Private Walking Tour with A Guide ( Private Tour )

2 to 8 hoursFree Cancellation

$126$120

Skip the lines and uncover ancient wonders at Chicago’s Field Museum, home to SUE, the world’s most complete T. rex. Marvel at dazzling artifacts, real mummies, and hidden treasures from lost civilizations. Step into a world of discovery and adventure! Tour is available in following language: English Spanish & French Highlights: • Explore the Field Museum of Natural History with a 5-Star Private Guide • Skip the line and dive straight into world-class exhibits with ease • See SUE the T. rex, ancient mummies, and dazzling gemstones up close • Learn fascinating secrets of dinosaur fossils and Ancient Egypt artifacts • Discover millions of years of history with expert insights at every step Stand face-to-face with a giant T. rex and unlock the mysteries of ancient worlds with Rosotravel! Experience the magic of Chicago’s Field Museum of Natural History with Skip-the-Line Tickets and a Licensed Private Guide. Step into adventure with us today!

Field Museum of Natural History Chicago Tour with Tickets

Field Museum of Natural History Chicago Tour with Tickets

Discover the stories, styles, and spirit that built Chicago into the architectural capital of the world. On this walking tour through the Loop, you’ll explore the birthplace of the skyscraper, visit landmarks like the Chicago Theatre, the Pablo Picasso at the Daley Plaza, and Millennium Park, and see how the city rose from the Great Fire to define modern design. Led by a friendly local guide who’s passionate about Chicago’s history and architecture, this tour brings the skyline to life one building, story, and photo stop at a time. Whether you’re an architecture enthusiast, a first-time visitor, or a curious local, you’ll walk away seeing Chicago in a whole new way.

Downtown Chicago Loop Walking Tour (Private)

Downtown Chicago Loop Walking Tour (Private)

$27$26

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

Chicago Downtown Sports History Tour - An App-Guided Adventure

Chicago Downtown Sports History Tour - An App-Guided Adventure

$5$5

Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat for the elite to a vibrant, diverse community shaped by migration, policy, and social change. Explore iconic landmarks like the Museum of Science and Industry while gaining insight into the impacts of racial segregation and urban renewal. This tour is designed for history buffs and urban studies enthusiasts, offering a nuanced perspective on the intersection of race and community development. - Walk through Hyde Park and learn about its historical significance - Visit key sites related to civil rights and urban policy - Understand the neighborhood's transformation and ongoing challenges - Perfect for history lovers and those curious about social dynamics

Hyde Park Walking Tour History Race and Urban Change

Hyde Park Walking Tour History Race and Urban Change

3 hoursFree Cancellation

$5$5

Step into the vibrant, resilient heart of Chicago's South Side. On this immersive journey through Bronzeville, you will uncover the epic story of the Great Migration—a time when millions of African Americans fled the Jim Crow South to build a self-sustaining 'Black Metropolis'. From the birthplace of gospel music to the headquarters of a newspaper that changed the nation, discover the triumphs of entrepreneurship, the brilliance of cultural innovation, and the unyielding spirit of a community that shaped modern America. A 3.9 km self-guided tour with 7 stops over 121 min Ideal for travelers interested in Identity, Migration & Globalization and History & Memory Immersively told in a podcast style by experts and locals Matching audio content, AI guide and navigation through the app

Podcast Tour Chicago The Promised Land and the Black Metropolis

Podcast Tour Chicago The Promised Land and the Black Metropolis

2 hours 1 minuteFree Cancellation

$7$7

The Bloomingdale Trail was built on a former railway line that once served as the industrial backbone of Chicago's north side. On this self-guided audio tour through Bucktown and Wicker Park, you'll hear how the factories, immigrants, and artists who lined these tracks transformed two scrappy neighbourhoods into some of the city's most sought-after real estate. The tour starts at Walsh Park, the eastern terminus of The 606, named with a nod to Chicago's universal zip code prefix. Further along, you'll stop at the Damen Avenue Arts Plaza, where the Flat Iron Arts Building stands as a reminder of how artists were deliberately recruited to revive a struggling neighbourhood. The tour ends at Western Avenue, the longest continuous city street in the world at 24.5 miles, where the trail continues west into Logan Square and Humboldt Park.

Bucktown and Wicker Park’s 606 Trail: A Walking Tour

Bucktown and Wicker Park’s 606 Trail: A Walking Tour

30 minutes to 1 hourFree Cancellation

$5$5

Chicago is inseparable from its Black history, where local pioneers helped shape the city’s story. On this self-guided audio tour through downtown Chicago, you’ll hear untold stories of Black excellence, resilience, and activism that transformed both the city and the nation. From Underground Railroad stations to civil rights battlegrounds, you’ll discover how Chicago became a beacon for those seeking freedom and opportunity. Starting at the site of Jean Baptiste Point DuSable’s mansion near the Chicago River, you’ll follow the footsteps of the city’s founder: a Black man who established Chicago’s first trading post in the 1770s. You’ll walk through the heart of the Loop, exploring sites where pioneering entrepreneurs like John Jones built businesses that became platforms for activism. The tour ends at Grant Park, where Barack Obama delivered his historic presidential acceptance speech in 2008 – a moment that represented the culmination of generations of struggle.

Resilience and Revolution: Audio Tour of Chicago’s Black History

Resilience and Revolution: Audio Tour of Chicago’s Black History

2 hours to 2 hours 30 minutesFree Cancellation

$15$14

Trace a century of daring architectural gambles in Chicago's Loop. From six-foot brick walls to soaring glass curtain walls, discover how engineers conquered swamp soil, roaring fires, and howling winds to invent the modern skyscraper. - A 1.6 km self-guided tour with 8 stops over 96 min - Ideal for travelers interested in Urbanism, Infrastructure & Innovation and Art, Design & Aesthetics - Immersively told in a podcast style by experts and locals - Matching audio content, AI guide and navigation through the app

Podcast Tour Engineering Skyward Chicagos Vertical Pioneers

Podcast Tour Engineering Skyward Chicagos Vertical Pioneers

1 hour 36 minutesFree Cancellation

$7$7

Venture along Michigan Avenue on an interactive tour to uncover Chicago's hidden gems and iconic landmarks. Dive into the city's rich history, answer trivia, and complete challenges for a unique experience blending sightseeing with gaming. Explore the Magnificent Mile and Cultural Mile with this unique adventure: Solve puzzles, explore the city, and find hidden gems at your own pace. Try a new type of experience with your smartphone, the perfect mix between a walking tour, sightseeing, and a scavenger hunt.

Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game

Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game

1 to 2 hoursFree Cancellation

$17$16

This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the neighborhood’s transition from a wealthy enclave to a gritty artist hub and its modern gentrification. Key Highlights: * Radical History: Learn about labor leader Lucy Parsons and the search for hidden bombs in the park. * Beer Baron Row: Hear tragic tales of murder and madness tied to grand Victorian mansions. * Quack Medicine: Discover how Theophilus Noel’s "Vita-Ore" empire funded iconic local architecture. * Mob Intrigue: Visit the former Russian Baths where mobsters met in steam rooms to avoid FBI wires. * Massacre Connections: See where the St. Valentine’s Day Massacre was planned and its getaway car destroyed.

Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour

Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour

45 minutes to 1 hour 15 minutesFree Cancellation

$10$9

Discover how a city of rigid steel and glass skyscrapers transformed its streets into a world-class, democratic art gallery. On this immersive walking tour through Chicago's Loop, you will uncover the dramatic, controversial, and inspiring stories behind the city's most iconic monumental sculptures. From Picasso's misunderstood masterpiece to the interactive joy of the Crown Fountain, learn how these colossal works of art challenged the public, defied architectural norms, and ultimately became the beloved soul of the Windy City. - A 2.4 km self-guided tour with 6 stops over 89 min - Ideal for travelers interested in Art, Design & Aesthetics and Urbanism, Infrastructure & Innovation - Immersively told in a podcast style by experts and locals - Matching audio content, AI guide and navigation through the app

Self-Guided Podcast Tour Chicago: The Loops Monumental Canvas

Self-Guided Podcast Tour Chicago: The Loops Monumental Canvas

1 hour 29 minutesFree Cancellation

$7$7

Winner of 10 Best History Tours by USA Today in 2026, and the "ORIGINAL" Chinatown tour since 2001. Discover the history, culture, and hidden stories of Chicago’s Chinatown on a guided walking tour through one of the city’s most vibrant neighborhoods. Starting at Chinatown Library, you'll visit iconic landmarks, including Chinatown Square, Chinatown Mural, Ping Tom Memorial Park, the Chinatown Gate, Nine Dragon Wall, Pui Tak Center, Chinese Buddhist Temple, St. Therese Chinese Catholic Church, and more. Along the way, you'll learn about Chinese heritage, local traditions, and the community’s lasting impact on Chicago before ending at the historical old Chinatown. - Explore Chicago Chinatown with a knowledgeable guide. - Learn about Chinese culture, history, and traditions. - Admire public art and the Chinatown Mural - Perfect for first-time visitors and returning guests alike

Chinatown History and Culture Tour

1 hour 30 minutesFree Cancellation

$25$24

Bucktown has a knack for keeping secrets - and most of them are deeply unsettling. On this self-guided walking tour, you'll hear the true stories behind the neighborhood's murders, hauntings, and disappearances, encountering a real-life fugitive, the ghost of a pub owner who still tends bar, and a winged creature with red eyes spotted across Chicago. Starting at the former Lincoln Tavern, where a 1980 robbery ended in multiple murders, you'll pass the spot where a 12-year-old boy was killed by a train in 1902. You will see where residents still report signs of his presence, and walk by the only Opus Dei-operated church in the country. The tour ends at Club Lucky, where three bullet holes still visible in the bar mark the spot where a Polish immigrant named Walter met his unfortunate end in January 1967. Sweet dreams.

Dark Tales of Bucktown: A Self-Guided Chicago Tour

Dark Tales of Bucktown: A Self-Guided Chicago Tour

40 minutes to 1 hour 20 minutesFree Cancellation

$12$11

Chicago, a city with undeniable charm, awaits you for a walking exploration of its 25 must-see attractions. From the Riverwalk to Marina City to the famous Cloud Gate, this tour takes you through the history and architecture of Windy City. See iconic venues like the Chicago Theatre and Willis Tower, while learning fascinating stories about Al Capone and Prohibition. An enriching experience for architecture, history and gastronomy lovers, all in one day. - 7.2 km tour through points of interest in Chicago - Discover the historical and modern heritage of the city - Explore at your own pace with captivating audio stories - Ideal for travelers in a hurry or those on a quick visit to Chicago

GPS Audioguide app: From Loop to Millennium Park (Offline).

Chicago Audio Guided Walking Tour 3h and 25 Audio Commentaries

3 hoursFree Cancellation

Explore the highlights of Chicago’s Chinatown in just 90 minutes with our expert-guided History and Culture Tour. This tour takes you through iconic landmarks, historic streets, and cultural sites, sharing authentic stories and insights along the way. Perfect for first-time visitors or those short on time, it’s a quick yet meaningful introduction to one of Chicago’s most vibrant neighborhoods. 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.

90 minute Chicago's Chinatown History and Culture Tour

1 hour 30 minutesFree Cancellation

$30$29

Discover many of Chicago’s top landmarks on a walking tour of the city—and bring kids along for the experience—on this private, family-friendly tour. Pick between a range of start times to suit your busy schedule, meet your guide in Millennium Park, and get ready to explore. You can look forward to seeing highlights from soaring skyscrapers to “the Bean,” all while learning amusing Chicago stories.

Private Family Walking Tour in Chicago Loop Cultural District

Private Family Walking Tour in Chicago Loop Cultural District

$669$636

3 hours 30 minutesFree Cancellation

Walking Prohibition Tour

Step into the birthplace of the modern skyscraper on this immersive walking tour through Chicago’s historic Loop. Discover the stories, innovations, and hidden details behind the buildings that shaped the modern city. What makes this experience unique: • Small-group tour for a more personal experience • Story-driven guiding that brings Chicago’s architecture to life • Focus on early skyscrapers and hidden architectural details • Visit iconic landmarks in the historic Loop • One complimentary copy of my book, Chicago Beyond the Bean, is included per booking.

Chicago Early Skyscraper Walking Tour in the Loop

$39$37

Logan Square Walking Tour Experience

1 hour 20 minutesFree Cancellation

Chicago Gangsters and Ghosts Walking Tour

$35$33

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Must-Dos in Chicago

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What are people saying about Chicago

Avery_W, Oct 2026

Do iiiiiit

This experience was probably one of the best parts of our trip. We were so surprised. Tanner was really engaging with his story telling, he made you want to keep listening and learn about the history of Chicago. I would highly recommend this to anyone that loves history and/or Chicago. We really loved our experience. Give Tanner a raise!!!!!!

Chicago's Chinatown Food and Walking Tour

Lucy_G, Oct 2026

Best food tour in Chicago

Great way to learn about Chinese food, meet people, and have a great, delicious meal. We had Cantonise dumplings and noodles, Szechuan chicken and rice, lamb sandwich from Xian, and we finish with a custard pastry. All the food was delicious. Highly recommended.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Zandra_R, Oct 2026

Book this! You won’t regret

Heath is an excellent guide The tour is expertly delivered and there was structure, flow, intentionality We really really enjoyed the tour and was glad we went ahead with booking as we would have never gone to this places and understood the history and significance of these structures! Thank You Heath ! Anyone coming to Chicago should do your tour It’s a must to have an enjoyable organised tour

Lake Michigan Sunset Cruise in Chicago

michelle_m, Oct 2026

Solo Vacation Week -KCMO Visitor

I have always wanted to have a fun adventure. My bucket list of my things to do includes riding the Subway Train, Boat Ride on Lake Michigan as the Sun sets and be Solo. It's been a challenging year for me. I lost a family member, a personal friend and a professional colleague of mine. This is my way of honoring my friends and family and celebrating them.

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Meghan_P, Oct 2026

Andre was friendly,...

Andre was friendly, informative and fun! We enjoyed the tour and learned a lot about not only “ haunted” Chicago but also some of the general history. It goes by quickly and was not tiring at all. We had great weather so it was very comfortable. He had dinner recommendations and very willing to answer any question. I’d recommend!

Chicago Architecture Tour: Underground Pedway and the Loop

baldy44, Oct 2026

Even though I worked in...

Even though I worked in the Loop for 10 yrs, I hadn't used the pedway. Guide Colleen was fun, knowledgeable, personable, and taught us interesting bits of Chicago history never heard before. She also created a nice connection among our small 6-person tour (people who didn't know each other before the tour).

Bike Tour of Chicago's Lakefront Neighborhoods

Willem_B, Sep 2026

Great afternoon!!!

We had a great bike ride with Kevin our guide. He showed and told a lot about Chicago. His enthusiasm was contagious. With our club of European diversity, he made a connecting group. We really enjoyed this afternoon. This is really recommended!!! And nice bikes!!! Kevin, thanks again 🚴🚴‍♀️🚴‍♂️🚴🚴‍♀️🚴‍♂️ warm regards, from Willem and Roos, the Netherlands

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Jan_B, Sep 2026

Great intro to the food and history of Chicago

This was an easy biking 3 1/2 hour tour for the evening tour. Just a note the tour does go rain or shine, and we definitely got caught in the rain towards the end! Our guide, Nora, was a native of Chicago and gave us lots of fascinating history of both food and the city.

Chicago Architecture and True Crime: Halloween Edition

Arite_M, Sep 2026

Entertaining, easy to follow – highly recommended!

David made our Chicago Crime & Architecture Tour a real highlight. You can tell he has comedy genes: he presents even complex topics in an incredibly entertaining, engaging, and easy-to-follow way. Although we’re not native English speakers, we could understand him perfectly and truly enjoy the tour. His mix of humor, knowledge, and storytelling turns this into much more than a standard guided tour. Highly recommended for anyone who wants to experience Chicago in a unique and memorable way!

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

Candace_W, Aug 2026

Just do it!

My family and I did this tour while we were in Chicago this past weekend and we were very happy with our experience. Sue was our guide and she was a wealth of knowledge. You could really tell that she enjoys her job. Before we got started, she made sure that everyone in our group was accounted for and even went out of her way to ensure that a few unintentional latecomers were able to jump in without disruption. She was well-prepared with anything we would've needed like wet wipes, hand sanitizer and even a Tide pen! All of the food options were amazing, with the Lou Malnati's pizza being my favorite dish. I would 100% recommend this tour to anyone visiting Chicago! You'll feel like a local for a few hours. :)

Private 45-Minute Chicago Skyline Helicopter Tour

Richard_W, Aug 2026

Our Family day in the sky...

Our Family day in the sky was absolutely perfect! There were a few nerves when we arrived but pilot answered all of our questions and guide us on an unforgettable tour, circling downtown, Navy pier, the Stadiums, Chicago River - it was incredible. If you are thinking about it, just do it! It’ll be a memory that will last a lifetime.

Chicago Night Crimes Tour by Bus

Nicolette_R, Jun 2026

Best use of time, No Regrets!

The tour was amazing! I was happy to be driven around downtown area and learn of the various neighborhoods, in addition to the crime history. The tour guide and driver were wonderful! No comments or recommendations, very happy tourist! Can’t wait to come back and bring more riders! See you soon Chicago Crime Tours!