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Top Chicago City Tours

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87 Chicago City Tours

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Did you know?
You can reserve your spot today and pay when you're ready.Learn more

Chicago Crime and Mob TourBus Tours

Chicago Crime and Mob Tour

star-4
Explore Chicago'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, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$39.95 
From  
US$39.95 
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  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Big Bus Chicago Hop-On Hop-Off TourBus Tours

Big Bus Chicago Hop-On Hop-Off Tour

star-4.5
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while live commentary onboard gives you insight into the city's colorful history.
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$29.00 
From  
US$29.00 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago City Minibus Tour with Optional Architecture River CruiseBus Tours

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Chicago City Minibus Tour with Optional Architecture River Cruise

star-4.5
Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside neighborhoods. You have a chance to get out and 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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Small group
  • 2 to 4 hours
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  • Free Cancellation
From  
US$39.45 
From  
US$39.45 
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  • 2 to 4 hours
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  • Free Cancellation

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Gangsters and Ghosts Tour in ChicagoCultural Tours

Gangsters and Ghosts Tour in Chicago

star-4.5
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$27.00 
From  
US$27.00 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago by Night Helicopter TourHelicopter Tours

Chicago by Night Helicopter Tour

star-5
Fly over the sparkling Chicago skyline at night on this helicopter tour. During this 15-minute tour, listen to engaging commentary from your expert pilot as you fly over sights like the Willis Tower (formerly the Sears Tower), Millennium Park, Lincoln Park and the Shedd Aquarium. Comfortable in a state-of-the-art, heated helicopter, enjoy panoramic views of the Lake Michigan shoreline and the city sprawling out below you. Tour route is subject to change.
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Small group
  • 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$179.00 
From  
US$179.00 
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  • 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago Helicopter TourLuxury Tours

Chicago Helicopter Tour

star-4.5
On a daytime helicopter tour over Chicago, enjoy views of the city's famed architecture and other sights from the air. Fly over Willis Tower (the old Sears Tower), Wrigley Field, Lincoln Park, and more while a pilot provides commentary about the city as you go.
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Small group
  • 12 to 15 minutes
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  • Free Cancellation
From  
US$154.99 
Price varies by group size
From  
US$154.99 
Price varies by group size
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  • 12 to 15 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Private Custom City Tour in ChicagoHalf-day Tours

Private Custom City Tour in Chicago

See Chicago the way you want to see it. This private tour is fully customizable to your specifications. Whether you are interested in the architecture and history, the art, the cool neighborhoods, or peaceful parks and happening beaches, this tour will cater to your tastes. Work with a guide to discover Chicago your way.
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Private experience
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$660.00 
per group
From  
US$660.00 
per group
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Loop Interior Architecture Walking Tour with PedwayArchitecture Tours

Loop Interior Architecture Walking Tour with Pedway

star-5
Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this walking tour. Your expert guide will share insights about interior architectural features of this design-rich city—from mosaic domes to the sprawling Chicago Pedway System—bringing the details of the Windy City into vivid focus. Stop to admire Chase Tower, the Marshall Field and Company Building, the Chicago Cultural Center, and more.
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Small group
  • 2 hours
From  
US$29.00 
From  
US$29.00 
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  • 2 hours

Underground Donut Tour - Chicago's First Donut TourFood Tours

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Underground Donut Tour - Chicago's First Donut Tour

star-5
Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$30.00 
From  
US$30.00 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private Chicago City Sights Helicopter TourPrivate Sightseeing Tours

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Private Chicago City Sights Helicopter Tour

star-4.5
You and a guest will soar above Chicago’s skyscapers, shoreline and iconic sights on a private, 15-minute helicopter tour of the city. Communicate with your personal pilot through a two-way headset, and personalize your flight to your interests. Capture extraordinary aerial images of the city scape as you fly past Lincoln Park and Lake Michigan, then spot Willis Tower, the John Hancock Building and the gleaming Trump Tower. Bank high above Millennium Park and enjoy views of the Windy City from the comfort of a climate-controlled private helicopter. Tour route is subject to change.
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Private experience
  • 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$408.00 
From  
US$408.00 
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  • 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Go Chicago Explorer Pass with SkyDeck and 360 ChicagoMulti-day Tours

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

star-4.5
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Go Chicago Explorer Pass saves you up to 42 percent on regular ticket prices. Create your own sightseeing itinerary by choosing 3, 4, or 5 attractions, tours, and activities from among more than 25 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: You can enjoy the extra flexibility in case your travel plans need to change—all passes are valid for one year from purchase date and only become activated with your first attraction visit. After activation, your pass will be valid for 30 days and/or the remaining number of attraction choices purchased.
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  • 30 days
From  
US$66.00 
From  
US$66.00 
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  • 30 days

Chicago Style Food TourHalf-day Tours

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Chicago Style Food Tour

star-4.5
Discover Chicago’s food, history, architecture and culture on this small-group walking tour. Try the Windy City’s quintessential staples from local restaurants and specialty food shops like Downtown Dogs and the world-famous Billy Goat Tavern. Taste local favorites including deep-dish pizza, a Chicago-style hot dog, and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural, and architectural components that make up this legendary town.
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  • 3 hours
From  
US$71.47 
From  
US$71.47 
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  • 3 hours

Sin & Suds Chicago Beer TourHalf-day Tours

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Sin & Suds Chicago Beer Tour

star-5
Explore Chicago’s Loop and South Loop neighborhoods — and get a taste of some local beverages — on this guided, 3-hour beer tour. Visit popular downtown establishments, sample some of the city’s finest brews and learn how beer goes with Chicago’s criminal past, discovering the basics of the Windy City’s vice history. From Al Capone and the local mob scene to the infamous Sands, the toughest criminal district in the city — this tour creates a unique experience that is both fun and memorable. Beer tastings plus a pizza pairing at one location included.
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$71.47 
From  
US$71.47 
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago City Sights Helicopter TourHelicopter Tours

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Chicago City Sights Helicopter Tour

star-5
Soar above the incredible skyline of Chicago during this 15-minute helicopter flight above the Windy City. Climb aboard your high-tech helicopter for a ride like no other, admiring views of Lake Michigan plus iconic city sights like Millennium Park, Lincoln Park, Navy Pier, the Shedd Aquarium and the Willis Tower. Along the way you'll hear informative details about the various landmarks from your pilot, who will provide commentary during the flight. Tour route is subject to change.
...  More
Small group
  • 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$179.00 
From  
US$179.00 
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  • 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Lonely Planet Experiences: River North Historical Food TourLuxury Tours

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Lonely Planet Experiences: River North Historical Food Tour

star-5
Get to know the food offerings in River North on this small-group walking tour. As you explore, listen to in-depth commentary from your guide on the culinary history of Chicago and the culture of the River North neighborhood. With a small group of just 12 fellow food-lovers, you'll enjoy personalized attention and the chance to chat about your favorite tastings. Samples include the classic Italian beef, a Chicago-style hot dog, and the famous deep dish pizza.
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Small group
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$60.96 
From  
US$60.96 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago Favorites Ultimate Food & Walking TourBeer & Brewery Tours

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Chicago Favorites Ultimate Food & Walking Tour

star-5
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.
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  • 2 hours 30 minutes
From  
US$62.99 
From  
US$62.99 
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  • 2 hours 30 minutes

Famous Tastes of Chicago Food TourHalf-day Tours

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Famous Tastes of Chicago Food Tour

star-4.5
Discover Chicago’s food, history, architecture and culture on this 3-hour, small-group walking tour. Try six of the Windy City’s quintessential staples from local restaurants and specialty food shops like Pizano’s Pizza and the Berghoff, the oldest family run-establishment in Chicago. Taste local favorites including deep-dish pizza,  Chicago Italian Beef Sandwich and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural and architectural components that make up this legendary town.
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  • 3 hours
From  
US$68.50 
From  
US$68.50 
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  • 3 hours

Chicago City Minibus TourBus Tours

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Chicago City Minibus Tour

star-5
NOTE: WE ARE ONLY OPERATING PRIVATE TOURS UNTIL AT LEAST EARLY MAY, DUE TO COVID 19. Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its many attractions. The small-group atmosphere with maximum of 12 people ensures a more personal experience. 
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Small group
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$39.45 
From  
US$39.45 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago Grand Half-Day TourHalf-day Tours

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Chicago Grand Half-Day Tour

star-3.5
Get the perfect introduction to the wealth of sights in the Windy City during this 4-hour Chicago day tour. Discover the many landmarks spanning both the city's North Side and South Side, enjoying a scenic ride along Lake Michigan on Chicago's Outer Drive along the way. You'll also have the chance to admire the city's Washington and Grant Parks, explore inside the Lincoln Park Conservatory, see Adler Planetarium and visit the iconic Wrigley Building. This Chicago in a half day tour also includes transport between all sites and tour narration.
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  • 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$52.95 
From  
US$52.95 
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  • 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago South Side Tour with Optional River CruiseBus Tours

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Chicago South Side Tour with Optional River Cruise

star-4
See the landmarks of Chicago’s South Side on a 2-hour coach tour through this historic, diverse and culturally-rich neighborhood. Take in views of Jackson Park and the University of Chicago, pause at the foot of the stunning Lake Point Towers then watch the bustling crowd at Navy Pier. Get a glimpse of American history as you explore President Obama’s former neighborhood and see the President and First Lady’s home; with an optional upgrade, you can finish your trip with a scenic cruise along the Chicago River.
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$34.95 
From  
US$34.95 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)Attraction Tickets

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

star-3.5
This Chicago grand tour covers four hours of sightseeing with admission to 360 Chicago (John Hancock Observatory). Get oriented to the Windy City on a coach tour that takes you along a scenic route on Lake Shore Drive, and past North Side and South Side highlights including Museum Campus, Lincoln Park, Washington Park, Grant Park and Wrigley Field. Finish on the 94th floor of the Hancock Center, one of Chicago's tallest landmarks, for panoramic views of the Magnificent Mile from the open-air observation deck.
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  • 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$73.95 
From  
US$73.95 
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  • 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago's Chinatown Food and Walking TourHalf-day Tours

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Chicago's Chinatown Food and Walking Tour

star-4.5
Explore Chicago's Chinese food scene on this walking tour in the Chinatown district. With a guide, learn about the cuisine of different regions of China and how Chinese culture has influenced Chicago and other areas. Enjoy included tastings from restaurants and other food venues in Chinatown—a great way to start a night out in the city.
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$62.99 
From  
US$62.99 
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago's Ultimate City Bike TourBike & Mountain Bike Tours

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Chicago's Ultimate City Bike Tour

star-5
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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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$45.99 
From  
US$45.99 
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago North Side TourBus Tours

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Chicago North Side Tour

star-4
Explore the North Side of Chicago on this guided sightseeing tour by coach. During this 2-hour tour, experience the bustle of the Loop, the central business district and one of the financial centers of the country. Visit State Street, an important thoroughfare in Chicago's history and the Magnificent Mile along Michigan Avenue. Learn about the history and culture of the city from your local guide; upgrade your tour to include a Chicago River cruise.
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$34.95 
From  
US$34.95 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation


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