Walking & Biking Tours in Chicago

Chicago Gangsters and Ghosts Walking Tour (opens in a new tab)

333 2 h

We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn. Walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through this now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing outside the Congress Hotel, one of the most haunted places in Illinois.

Free cancellation

Chicago Favorites Ultimate Food and Walking Tour (opens in a new tab)

2,405 3 h

The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the beautiful streets of downtown & taste the Windy City’s favorite eats on this iconic Chicago Food Tour! Bobby’s Bike Hike & Food Tours, whose food tours rank Top 20 worldwide on Tripadvisor, offers this ultimate walking & food experience featuring the hard-working, salt-of-the-earth classics Chicago made famous: a slice of deep dish pizza, a Chicago-style hot dog, Italian beef, popcorn & dessert. Expert guides lead you through downtown’s most iconic landmarks on our Day tours—Millennium Park, Chicago Theatre, Riverwalk, Michigan Ave—Night tours go a different route, please check itinerary for details-we share Chicago’s rich, food-loving history. It’s one of the tastiest Things to Do in Chicago! Enjoy your tour & get a BONUS 2-hour FREE bike or kayak rental gift per ticket. Cruise the Lakefront Bike Trail or paddle Lake Michigan for extra fun!

Chicago's Chinatown Food and Walking Tour (opens in a new tab)

851 3 h

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked Top 10 in America by USA Today & Top 20 in the world by Tripadvisor, for a day of interesting stories and scrumptious eats on this delicious Food Tour in Chinatown. This 3-hour Walking and Chintown Food Tour, you’ll see the bustling Chinatown Square, then get to sampling some of the richest cuisine around; including Cantonese dim sum, Portuguese-Chinese bakery treats, Szechuan style, and even Xi'an cuisine, all while learning about the history of how these foods & culture arrived in Chicago. This is a totally unique culinary tour experience, and not to be missed! Upon arrival to the tour, you can add a VIP Drink option for alcoholic and ethnic drink pairings! Chinatown can be challenging to navigate on your own, so let our expert local guides show you the way & discover 5 of our all-time favorite dishes.

Chicago Architecture and True Crime: Halloween Edition (opens in a new tab)

739 1 h 30 min – 1 h 45 min

Get the best of both worlds: explore Chicago’s stunning architecture while uncovering its dark past. Inspired by Devil in the White City, this expert-led walking tour reveals the secrets of the city’s skyline and its shadowy history. If it’s raining/too hot the tour is almost all INDOOR. Led by a passionate local guide, you’ll visit architectural gems and hidden landmarks that BOAT TOURS MISS bringing Chicago’s rich and eerie past to life.

Chicago: Gangsters and Food Tasting Walking Tour (opens in a new tab)

49 2 h

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine and the gangsters who ate it all in one special unique tour! Sample Chicago’s deep dish – as well as prime steak and the world famous “Chicago hot dog" all while treading the streets of Capone’s closest friends and dreaded enemies. Highlights include a visit to an old tunnel used by prohibition gangsters in the basement of one of the establishments; a mansion once used as a brothel for gangsters; the Cathedral where gangsters were gunned down by Capone’s men; and a restaurant owned by the man who brought down what was left of the Chicago mafia in the early 2000’s. Gluten-free/vegan/vegetarian options are available (please reach out prior to the tour to inform us of any dietary requirements.)

Chicago's Secret Interiors Architectural Walking Tour (opens in a new tab)

99 2 h

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.

Chicago in a Day Walking Tour: Food, History & Architecture (opens in a new tab)

1,464 4 h 30 min

Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging in delectable local cuisine. From deep-dish pizza to hidden gems, savor the flavors of Chicago as a knowledgeable guide unveils the city's culinary secrets and fascinating history.

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour (opens in a new tab)

490 1 h 30 min

Walk in the footsteps of Al Capone, John Dillinger, and real life ghost stories while hearing tales of Chicago's haunted past. Visit Prohibition Era speakeasy bars, sites of real life mob shootouts, and haunted tragedies that shape the city's legacy. This walking tour blends ghost stories, true crime history, and architectural landmarks to reveal the beauty and horror from one of America's most famous time periods, right where it happened. You'll gain special access to architectural interiors tied to famous history, as you are led by a trained historian tour guide through these famous sites. Learn where Chicago's history still whispers after dark!

Original Chicago Architecture Interiors Tour: Dazzling Interiors (opens in a new tab)

1,889 2 h

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's exclusively offered interiors-themed tours in Chicago for more than a decade, and that's INSIDE CHICAGO WALKING TOURS. Our "World Within: Dazzling Interiors of the Loop" tour is Chicago's first and best architecture interiors tour. Accept no imitations! Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t shown them by a seasoned, in-the-know tour guide. Ranging from stained glass mosaics from the turn of the century to soaring Art Deco spaces from the Roaring 20s, these spaces are some of the most beautiful in the city -- and open to us to explore!

Art Institute of Chicago Skip-the-Line Exclusive Guided Tour (opens in a new tab)

364 2 h 30 min

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour exclusive guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. Highlights Generally Include: (if artwork is not on loan or being restored etc.) Paris Street, Rainy Day by Gustave Caillebotte Sunday on La Grande Jatte - Georges Seurat Sky Above Clouds - Georgia O'Keefe Nighthawks - Edward Hopper A Picture of Dorian Gray - Ivan Albright America Windows - Marc Chagall The Old Guitarist - Pablo Picasso Inventions of Monsters - Salvador Dali Four Mona Lisas - Andy Warhol

Free cancellation

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich (opens in a new tab)

1,054 3 h

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through some of the city's world renowned architecture and public art in the famed Chicago Loop District. Experience our famous deep dish pizza, taste the amazing Italian beef sandwich, enjoy gourmet popcorn, and lots of other treats. Plus, there is our mouth-watering secret dish that you can only find out about on the day of the tour!

Free cancellation

Chicago Architecture Tour: Underground Pedway and the Loop (opens in a new tab)

593 2 h

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famous and mysterious Chicago Pedway, a system of underground tunnels connecting 40 blocks downtown, popping in and out of buildings to see beautiful and fascinating interior spaces. You'll learn to use this system that most locals don't even fully know or use, and you'll be encouraged to continue exploring Chicago on your own after the tour!

Skip-the-line: Art Institute of Chicago Guided Tour (opens in a new tab)

691 2 h 30 min

Beat the crowds with an expert art historian guide on this exclusive early morning tour. Immerse yourself among the masterpieces housed within the acclaimed museum and listen as your guide brings each piece to life by sharing the story behind it. Let your guide lead you to the most important pieces of the 300,000-strong collection, taking the hard work out of finding where to go and what to see. Explore in a small group for a special, personal experience, and interact with your guide who can give insider’s insight into the museum.

Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle (opens in a new tab)

1 1 h – 2 h

Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Millennium Park and Riverwalk! Snap a picture by the famous Cloud Gate sculpture and get away from the hustle and bustle in the city’s most iconic park. Then, stroll along the picturesque riverside, admire Chicago’s totally unique architecture, and learn the fascinating stories behind the city’s skyline. This combo is the easiest, best way to get to know this complex city! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Private tourFree cancellation

Chicago Crime, Mobsters & Ghosts Walking Tour (opens in a new tab)

474 1 h 30 min – 2 h

Join us along the historic streets and alleys of Chicago as we walk among the spirits of mobsters and ghosts of the condemned. This tour is for lovers of history, true crime, and haunted mysteries. Expect a sultry and gritty cocktail of Chicago's darkest stories hiding in the shadows of the Loop. From Grant Park to the Alley of Death, your expert local guide will shed light on the city’s secrets. Prepare for thrills and just the right amount of chills.

Chicago Haunted Interior Architecture Ghost Tour (opens in a new tab)

26 1 h 30 min – 1 h 45 min

Take the best ghost tour in Chicago! Go inside 6/8 old buildings, learn about what makes them haunted and what also makes them cool! Learn from expert guides what makes Chicago one of the spookiest places in the world! Note, tour does not finish where it starts

Embers of the Windy City: Chilling Chicago Ghost Tours (opens in a new tab)

139 1 h

Come on our chilling ghost tour presented by US Ghost Adventures! Book Directly With Windy City Ghosts and save $5/person. Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy streets. Our Ghost Tour transports you back in time to an era of gangsters, bootleggers, bank robbers, and jazz babies. Windy City Ghosts nightly Ghost Tours take you through Lincoln Park, a beautiful North Side neighborhood with a twisted past. Learn about the forgotten burial ground that is the foundation of this bustling neighborhood. Check the bathroom mirrors in the Lion House of the Lincoln Park Zoo to make sure the ghost of a Victorian woman in white isn’t standing right behind you. Learn what spirit haunted Al Capone to the end of his days. On our Ghost Tour, you’ll hear the strange and disturbing tales associated with each of our carefully selected tour stops.

Skip the Line Chicago Art Institute Tour Semi-Private 12ppl Max (opens in a new tab)

253 2 h 30 min

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour semi-private (12 Guest Maximum) guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. Highlights Generally Include: (if artwork is not on loan or being restored etc.) Paris Street, Rainy Day by Gustave Caillebotte Sunday on La Grande Jatte - Georges Seurat Sky Above Clouds - Georgia O'Keefe Nighthawks - Edward Hopper A Picture of Dorian Gray - Ivan Albright America Windows - Marc Chagall The Old Guitarist - Pablo Picasso Inventions of Monsters - Salvador Dali Four Mona Lisas - Andy Warhol

Private Chicago Foodie Tour (opens in a new tab)

6 4 h

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, Garrett’s Popcorn, and Do-Rite Donuts while exploring top city landmarks such as the Tribune Tower, Wrigley Building, and Buckingham Fountain. Led by a friendly local guide, this experience blends Chicago’s most famous eats, rich culture, and great photo ops — the perfect way to enjoy the best of the Windy City in one delicious day. Tour Ticket Includes: • 1 Portillo’s hot dog • 1 small Garrett’s Popcorn • 6" Al’s Italian Beef Sandwich • 1 slice of authentic Chicago deep dish pizza

Private tourFree cancellation

Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour (opens in a new tab)

82 2 h

Discover Chicago’s dark side on a chilling 2-hour walking tour. Strolling just under 2 miles at an easy pace, we reveal stories of gangsters, tragedies, and restless spirits hidden behind the city’s glamorous façade. Hear of hidden mob headquarters, psychopaths in plain sight, and disasters like the Iroquois Fire and Eastland Disaster. Join us in exploring historic interiors where gangsters once gathered and ghosts are said to linger. Along the way, explore the roots of ghost lore—are they real sightings or tricks of architecture? Decide for yourself if Chicago’s most haunted tales are fact or fiction. Perfect for fall nights and curious minds, this tour blends true crime, gangster history, and ghost stories into an unforgettable experience.