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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  
US$ 39.95
From  
US$ 39.95
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SPECIAL OFFER

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
US$ 159.99
US$ 60.99 savings
From  
US$ 99.00
US$ 159.99US$ 60.99 savings
US$ 159.99
US$ 60.99 savings
From  
US$ 99.00
US$ 159.99US$ 60.99 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
US$ 179.99
US$ 36.00 savings
From  
US$ 143.99
US$ 179.99US$ 36.00 savings
US$ 179.99
US$ 36.00 savings
From  
US$ 143.99
US$ 179.99US$ 36.00 savingsSee Details

SPECIAL OFFER

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
US$ 79.00
US$ 3.00 savings
From  
US$ 76.00
US$ 79.00US$ 3.00 savings
US$ 79.00
US$ 3.00 savings
From  
US$ 76.00
US$ 79.00US$ 3.00 savingsSee Details

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  
US$ 124.00
From  
US$ 124.00
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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  
US$ 37.50
From  
US$ 37.50
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SPECIAL OFFER

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: 3 days
  • Free Cancellation
  • Duration: 3 days
  • Free Cancellation
US$ 37.00
US$ 6.01 savings
From  
US$ 30.99
US$ 37.00US$ 6.01 savings
US$ 37.00
US$ 6.01 savings
From  
US$ 30.99
US$ 37.00US$ 6.01 savingsSee Details

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  
US$ 27.00
From  
US$ 27.00
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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  
US$ 40.50
From  
US$ 40.50
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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  
US$ 49.95
From  
US$ 49.95
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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  
US$ 72.99
From  
US$ 72.99
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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
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$ 55.00
From  
US$ 55.00
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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  
US$ 28.00
From  
US$ 28.00
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Underground Donut Tour - Chicago's First Donut Tour

Sample some of the Windy City’s tastiest donuts on this 2-hour Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit four 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  
US$ 30.00
From  
US$ 30.00
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NEW TO VIATOR

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  
US$ 89.95
From  
US$ 89.95
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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  
US$ 37.00
From  
US$ 37.00
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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  
US$ 70.85
From  
US$ 70.85
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Chicago Pedway Walking Tour

Discover a lesser-known side of the Windy City on this Chicago Pedway tour, a 1.5-hour walking excursion through the many heated passageways, tunnels, and corridors that link some of the town's most iconic buildings. Follow your humorous guide on an insider's exploration of these relatively unknown walkways, learning about the area's architecture and history as you go. It's a great way to explore a different side of Chicago unknown to most visitors.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
US$ 23.00
From  
US$ 23.00
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Private Chicago Highlights Driving Tour

Get an insider’s look at the Windy City’s most iconic monuments during this 3-hour private tour. Travel through Chicago aboard a private vehicle as you discover some of the city’s top neighborhoods, including the Loop, River North, the Magnificent Mile (along Michigan Avenue), Streeterville, the Gold Coast and much more. Your private driver-guide and vehicle, bottled water and round-trip hotel transport are all included.
  • Duration: 3 hours
  • Duration: 3 hours
From  
US$ 99.00
From  
US$ 99.00
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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  
US$ 55.00
From  
US$ 55.00
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Chicago Style 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 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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$ 55.00
From  
US$ 55.00
See Details

Chicago Lakefront Neighborhoods Bicycle Tour

Pedal past the lakefront neighborhoods of Chicago's North Side on this 3-hour bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$ 49.99
From  
US$ 49.99
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Chicago Night Crimes Tour

Discover the ‘dark side’ of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine’s Day Massacre, learn about ‘The Enforcer’s Safe,’ and stop by local watering holes.
  • Duration: 2 to 2.5 hrs
  • Free Cancellation
  • Duration: 2 to 2.5 hrs
  • Free Cancellation
From  
US$ 45.00
From  
US$ 45.00
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Chicago City Tour and Chicago River Cruise

See Chicago from a new perspective during this 4-hour combined bus and boat excursion covering some of the city's most iconic sights. First discover Windy City landmarks such as the skyscrapers of the Loop, Grant Park, Shedd Aquarium, Soldier Field and the former stomping grounds of President Obama during a narrated coach tour. Then take a Chicago cruise aboard your state-of-the-art yacht, enjoying a cruise of the Chicago River that provides a unique look at the city's architecture from the water. This half-day Chicago exploration also includes hotel pickup.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
US$ 73.95
From  
US$ 73.95
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