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Top Chicago Tours & Sightseeing

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Chicago Crime and Mob Tour

Explore Chicago's gangster past on this 1.5-hour 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.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
$39.95
From  
$39.95
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Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

See Chicago from several angles, including the 103rd floor of Willis (Sears) Tower, where you have early access to the Skydeck. This Viator VIP package — available nowhere else — provides a crowd-free morning overlooking city landmarks from glass-enclosed balconies. Follow up your vista with a 2-hour narrated trolley tour past Grant Park, the John Hancock Center, the Wrigley Building and more. Finish with an afternoon cruise on the Chicago River and enjoy a complimentary drink as you discover the city's distinctive skyscrapers from an architecture-savvy guide.
  • Duration: 6 hours
  • Free Cancellation
  • Duration: 6 hours
  • Free Cancellation
From  
$124.00
From  
$124.00
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Chicago Explorer Pass

This is the easiest and most affordable way to explore some of Chicago's top attractions at your own pace. The Chicago Explorer Pass, valid for 30 days after first use, provides admission to your choice of three, four or five attractions, tours or activities that will save you up to 42 percent on regular ticket prices. Create your own sightseeing itinerary by choosing from among over 25 top sites and things to do, including Lincoln Park Zoo, Navy Pier and and LEGOLAND Discovery Center.
  • Duration: 30 days
  • Duration: 30 days
From  
$81.00
From  
$81.00
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Chicago Helicopter Tour

On a daytime helicopter tour over Chicago, enjoy views of the city's famed architecture and other sights from the air. You'll 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.
  • Duration: 15 minutes
  • Free Cancellation
  • Duration: 15 minutes
  • Free Cancellation
From  
$99.00
From  
$99.00
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Big Bus Chicago Hop-On Hop-Off Tour

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 14 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 on board gives you insight into the city's colorful history. Don't forget to snap a selfie in front of the shiny steel bean in Millennium Park!
  • Duration: 8 hours
  • Free Cancellation
  • Duration: 8 hours
  • Free Cancellation
From  
$29.00
From  
$29.00
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Gangsters and Ghosts Tour in Chicago

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$27.00
From  
$27.00
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Chicago City Minibus Tour with Optional Architecture River Cruise

Explore Chicago's iconic landmarks on this 2-hour sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus with a small group of twelve people or less. This ensures an intimate touring experience as you enjoy downtown and some North side neighborhoods. You will have a chance to get out and visit several locations such as the 1888 skyscraper called The Rookery, with its Frank Lloyd Wright designed lobby and the unparalleled skyline views from Museum Campus. Listen as your guide talks about the historical and cultural factors that make Chicago unique. The city tour ends at Millennium Park, home of the famous Cloud Gate sculpture, commonly referred to as "the bean."  Opt to upgrade your tour with a popular 75-minute open-top boat tour on the Chicago River that focuses on the city's renowned architecture. Pick-ups from most downtown Chicago hotels are included.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$37.50
From  
$37.50
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Chicago City Hop-on Hop-off Tour

On a Chicago hop-on hop-off tour, you can enjoy easy transportation around the city to see the sights that interest you most at your own pace. Select the pass you want when booking, and create your own itinerary in Chicago to check out attractions such as the Michigan Avenue, Navy Pier and Millennium Park. Hop off and on the double-decker bus whenever you wish, and listen to narration about the city on board.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$19.00
From  
$19.00
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Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this 4-hour bike tour through the windy city. You’ll cover about 13 miles (21 km), following an informative guide at a moderate pace through the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$77.99
From  
$77.99
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SPECIAL OFFER

Chicago Favorites Food and Walking Tour

Stroll through downtown Chicago on this 2.5-hour food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, brownies, and local beer. All tastings and beverages are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
$59.00
$3.01 savings
From  
$55.99
$59.00$3.01 savings
$59.00
$3.01 savings
From  
$55.99
$59.00$3.01 savingsSee Details

SPECIAL OFFER

Chicago Helicopter Tour Nighttime Experience

Soar above the city lights of Chicago on a 15-minute nighttime helicopter ride with live narration by experienced pilots. Enjoy birds-eye views of downtown landmarks, then bank past Navy Pier to Lincoln Park and Uptown. Hear about the history of the city as you take in unforgettable views of downtown’s bristling skyscrapers, and see Willis Tower, Millennium Park and Soldier Field. This unique experience offers a once in a lifetime view of the Second City at its most stunning.
  • Duration: 15 minutes
  • Free Cancellation
  • Duration: 15 minutes
  • Free Cancellation
$179.99
$36.00 savings
From  
$143.99
$179.99$36.00 savings
$179.99
$36.00 savings
From  
$143.99
$179.99$36.00 savingsSee Details

Chicago Prohibition Tour

Visit four historic bars in operation since Prohibition in Chicago, and learn from a knowledgeable guide about the surreptitious world of the speakeasy. This adults-only tour takes you by coach to once-illicit establishments in Old Town, Wicker Park and the Chicago Loop where liquor, jazz and mobsters ruled. You’ll hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban of alcohol. If you’d like, you can purchase recommended craft cocktails and signature drinks of the 1920s.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
$45.00
From  
$45.00
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Chicago Grand Half-Day Tour

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.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$49.95
From  
$49.95
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Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this 2-hour 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.
  • Duration: 2 hours
  • Duration: 2 hours
From  
$28.00
From  
$28.00
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Chicago Segway Tour and Skydeck Admission

Cruise through Chicago on this 2-hour Segway Tour. First-time visitors will see major attractions and get a great overview of the city. Those familiar with Chicago will deepen their knowledge with little-known facts and anecdotes. This tour includes tickets to the Skydeck at Willis Tower for incredible views of the lake and skyline. 
  • Duration: 2 to 4 hours
  • Free Cancellation
  • Duration: 2 to 4 hours
  • Free Cancellation
From  
$90.47
From  
$90.47
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City Sightseeing Chicago Hop On Hop Off Tour

See more of the Windy City with this money-saving, 2.5-hour, hop-on, hop-off sightseeing bus ticket. Enjoy informative on-board narration as you cruise by 13 Chicago landmarks including the Art Institute, Field Museum, John Hancock Building, and much more. A range of ticket validation periods, ranging from 24 to 72 hours, also help ensure maximum flexibility.
  • Duration: 1 to 3 days
  • Free Cancellation
  • Duration: 1 to 3 days
  • Free Cancellation
From  
$39.00
From  
$39.00
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Chicago Segway Tour

Glide around Chicago and along Lake Shore Drive past Lake Michigan on your very own Segway. After a 30-minute orientation session, you’re off to see highlights of the Windy City with an expert guide. View city sights such as Navy Pier, Buckingham Fountain, Museum Campus, Millennium Park, Grant Park and more. Select a 2- or 3-hour tour in the morning or afternoon. Numbers are limited to eight passengers per guide for a personalized experience.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$70.85
From  
$70.85
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Frank Lloyd Wright by Bus Tour from Chicago

Take a deep dive in to Frank Lloyd Wright's Prairie Style on this 4-hour architecture tour of Oak Park from Chicago. Listen to your guide's commentary during the trip, then take a walking tour of the Frank Lloyd Wright Historic District and a tour of the architect's home and studio.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$55.00
From  
$55.00
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Chicago Land and River Architecture Tour: North and South Shores

Whether you’re short on time or want to orient yourself to Chicago, a 3.5-hour land and river tour is the perfect option. The comprehensive itinerary takes you through both the North and South sides. Listen as your guide tells insider stories about the people who shaped the city. After the land tour, rest your feet and see the city from a unique vantage point during a 90-minute river cruise.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
$89.95
From  
$89.95
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Viator VIP: Architectural River Cruise and Chicago Helicopter Tour

Experience Chicago from the air and the water on this two-part tour that features a river cruise and a helicopter ride above the city. First, take a cruise down the Chicago River to learn about the architectural history of the town. Then, board a state-of-the-art helicopter and fly above the skyline. Both tours are fully narrated and you will see Navy Pier, Wrigley Field, Soldier Field, the John Hancock Center, Willis Tower, and more.
  • Duration: 15 to 90 minutes
  • Free Cancellation
  • Duration: 15 to 90 minutes
  • Free Cancellation
From  
$178.00
From  
$178.00
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Chicago by Night Helicopter Tour

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.
  • Duration: 15 minutes
  • Free Cancellation
  • Duration: 15 minutes
  • Free Cancellation
From  
$149.00
From  
$149.00
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Underground Donut Tour - Chicago's First Donut Tour

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 gluten- and nut-free options are also available.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$30.00
From  
$30.00
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Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

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.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$65.00
From  
$65.00
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Famous Tastes of Chicago Food Tour

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.
  • Duration: 3 hours
  • Duration: 3 hours
From  
$63.50
From  
$63.50
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(888) 651-9785
(888) 651-9785