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200+ results
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.
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Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
Free Cancellation
1 hour 30 minutes
from
$36
Explore a new side of Chicago and the city's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, John Dillinger, and more famous figures hung out. There are ample chances to get out of the bus and pose for pictures in front of a historic courthouse, among other infamous sites.
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Chicago Crime and Mob Bus Tour
Free Cancellation
1 hour 30 minutes to 2 hours
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$49
Enjoy an active and entertaining way to explore Chicago’s highlights with this small-group Segway tour. Meet your guide at a convenient location in downtown Chicago, get acquainted with your Segway before setting off, and then hit the road. You’ll discover top Windy City highlights, including Millennium Park, the Buckingham Fountain, the Museum Campus, and more, all while learning about the city’s history and insider facts from your guide.
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2-Hour Guided Segway Tour of Chicago
Free Cancellation
2 hours
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$65
Skip the guesswork and discover the real haunts of Capone, Dillinger, and The Outfit on a walking tour that then also you shows how those same streets become movie stars. Walk the city corners seen in *The Untouchables* and *Public Enemies,* and hear how Chicago wrote the script for American gangster history. This isn’t just another sightseeing tour—it’s a front-row seat to crime, cinema, and the city that made them both.
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Chicago Crime and Movies Tour
Free Cancellation
1 hour 30 minutes
from
$35
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.
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Chicago Food Tour: Taste the City’s Most Iconic Eats
Free Cancellation
2 hours
from
$87
Price varies by group size
Likely to Sell Out
Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.
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Chicago City Tour with Architecture River Cruise Option
Free Cancellation
2 to 4 hours
from
$50
Discover the dark side of the Windy City on this nighttime crime history bus tour of Chicago. Through your expert guide's rich storytelling, immerse yourself in tales of notorious mobsters like Al Capone, Frank Nitti, and Bugs Moran as you explore infamous crime scenes including the site of the St. Valentine’s Day Massacre.
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Chicago Night Crimes Tour by Bus
Free Cancellation
2 hours to 2 hours 30 minutes
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$55
Book in advance to take this popular tour that details the mob history of Chicago during the Prohibition Era (1920s-1930s). Learn about the exploits of gangsters like Capone, Dillinger, Moran, and others as you travel by minibus to sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine's Day Massacre. Your guide adopts gangster attire and characteristics that add dramatic flair to the historical commentary.
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Chicago's Original Gangster Tour by Bus
Free Cancellation
1 hour 45 minutes
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$48
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.
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Chicago Architecture Center River Cruise aboard First Lady
1 hour 30 minutes
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$57
First-time visitors to Chicago seeking a quick overview of the city will enjoy this 90-minute small-group walking tour. Your guide will take you to some of Chicago’s most beautiful and interesting buildings, including the Tribune Tower, the Art Institute, the Willis Tower, and more. Learn about Chicago’s architecture, history, and culture while getting your bearings.
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Chicago Walking Tour: Must-See Chicago
Free Cancellation
1 hour 30 minutes
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$35
Experience Chicago in Style with Our Luxury City Sightseeing Minibus Tour. Indulge in the ultimate Chicago adventure on our top-rated, luxury sightseeing minibus tour. This 2-hour, expertly guided experience takes you through the vibrant heart of the city in a sleek, climate-controlled minibus designed for comfort and class. Marvel at iconic skyline views and the shimmering waters of Lake Michigan from panoramic windows, and enjoy curated photo stops at the city's most breathtaking landmarks. With engaging stories from your private guide and an intimate, upscale atmosphere, this tour offers an unmatched blend of elegance and exploration. Please note, infants 0-3 years old must sit on a lap.
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Luxury Minibus Chicago City Tour
Free Cancellation
2 hours
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$65
Maximize your Chicago sightseeing on a river cruise—and travel aboard a unique historical vessel, which other tours don’t offer—on this one-of-a-kind excursion. Pick from different departure times and board a classic Chicago fireboat, which served the city’s fire department from 1937 to 1981. As you sail Lake Michigan and the Chicago River, view architectural highlights including the Wrigley Building and Chicago Lighthouse, and chart the boat’s firefighting history via the on-board displays and commentary.
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Historical and Architectural Chicago Fireboat River & Lake Cruise
Free Cancellation
2 hours
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$47
Step into Chicago’s coolest hidden bars on a mid-century cocktail adventure! Join a local guide to discover vintage lounges, secret speakeasies, and retro bars most tourists miss. Savor expertly crafted cocktails (own expense), hear untold stories of the city’s nightlife boom, and soak in stylish decor straight from the 1950s and 60s. This small-group tour is perfect for cocktail lovers, architecture buffs, and anyone seeking an off-the-beaten-path night out in the Windy City.
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5.0
(4)
Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour
Free Cancellation
1 hour 30 minutes
from
$51
Chicago is world-renowned for its architecture—and this small-group walking tour offers the ideal introduction to its iconic buildings, its architectural eras, and the starchitects who have left their impression on the city. Meet your guide at the Chicago Architecture Center and set off on foot: you’ll discover highlights like the Wrigley Building and Marina City, will see works by Renzo Piano and Frank Gehry, and will learn all about Chicago history.
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Chicago Walking Tour: Connecting Past and Present
Free Cancellation
1 hour 45 minutes
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$35
The Sloomooverse combines delicious scents (birthday cake, fresh berries, cotton candy), sounds that energize as well as soothe, an invigorating palette, and a feast of visual and tactile wonders. Plus, you’ll design your dream slime at our DIY Bar. Over 4,320,000 unique combinations! Play, connect, enjoy!
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Sloomoo Institute Chicago Admission: Make Your Own Slime
1 hour to 1 hour 30 minutes
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$40
See the Second City from the water with a sightseeing cruise along the Chicago River and the Lake Michigan shoreline, offering a unique perspective of towering skyscrapers and historic architecture. This tour offers stories about the city’s history and culture as you pass by Chicago's landmarks, museums, and buildings. Capture unforgettable images of the city skyline from Lake Michigan, ensuring a unique look at Chicago, perfect for all ages.
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Chicago Sightseeing River and Lake Cruise
Free Cancellation
1 hour 30 minutes
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$46
The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers. Located in the heart of downtown on Michigan Avenue, the observatory is steps away from other top Chicago attractions. It will be the high point (literally) of your Chicago trip! Upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. The Sip menu includes a rotating selection of beer, wine and cocktails. Once onsite, you can purchase tickets to TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. You may also choose to upgrade your Sip and View ticket from the Sip Menu to the Elevated Menu for an additional $8. *TILT not included in purchase
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360 Chicago Observation Deck Sip and View Ticket
Free Cancellation
2 hours
from
$44
Likely to Sell Out
Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.
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Chicago City Minibus Tour
Free Cancellation
2 hours
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$50
Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.
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2-Hour Chicago Lakefront & Museum Campus Segway Tour
Free Cancellation
2 hours
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$70
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.
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American Writers Museum Admission Ticket
Free Cancellation
1 to 5 hours
from
$16
Calling all fans of the paranormal, this evening ghost bus tour of Chicago takes you into the city’s darkest recesses—and reveals a side of the city few others get to experience. Travel with ease between locations where hauntings are reported to have taken place and listen to chilling tales delivered by your guide. The City Cemetery, the site of the notorious St. Valentine’s Day massacre, and more are all included.
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Chicago Hauntings Original Ghost Bus Tour
Free Cancellation
3 hours
from
$59
Likely to Sell Out
Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
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Chicago's Ultimate City Bike Tour of Top Downtown Attractions
Free Cancellation
3 hours
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$59
Head to one of Chicago’s top neighborhoods for food lovers—and try donuts from four of the Windy City’s top specialty bakeries—on this indulgent walking tour. Meet your guide at the Chicago French Market in the morning, and come hungry: you’ll enjoy four different donuts, each representing different culinary styles and traditions. As you go, wander the West Loop and Restaurant Row, and learn more about Chicago’s dining scene.
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Delicious Donuts & Sweet Treats: West Loop Walking Tour
Free Cancellation
1 hour 30 minutes to 2 hours
from
$70
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.
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Chicago Self-Guided Audio Tour
3 to 9 hours
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$6
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Art Institute of Chicago
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Skydeck Chicago at Willis Tower (Sears Tower)
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Chicago River
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Chicago Riverwalk
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The Magnificent Mile
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Art Institute of Chicago
From $12
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Chicago Theatre
From $12
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Skydeck Chicago at Willis Tower (Sears Tower)
From $12
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Chicago River
From $28
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