Top Chicago Tours & Sightseeing

Chicago Crime and Mob Tour

• 376 Reviews
• 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.
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Chicago Helicopter Tour

• 7 Reviews
• 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.
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Chicago Helicopter Tour Nighttime Experience

• 3 Reviews
• 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.
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Chicago City Hop-on Hop-off Tour

• 951 Reviews
• 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.
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Chicago City Minibus Tour with Optional Architecture River Cruise

• 104 Reviews
• 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.
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Chicago Explorer Pass

• 182 Reviews
• 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.
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Gangsters and Ghosts Tour in Chicago

• 10 Reviews
• 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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Big Bus Chicago Hop-On Hop-Off Tour

• 106 Reviews
• 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!
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Chicago Craft Brewery Barrel Bus Tour

• 3 Reviews
• Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided, 4-hour brewery tour. Visit three unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy approximately 50 ounces of beer total throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
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City Sightseeing Chicago Hop On Hop Off Tour

• 3 Reviews
• 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.
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Underground Donut Tour - Chicago's First Donut Tour

• 6 Reviews
• 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.
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Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

• 83 Reviews
• 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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Chicago Lincoln Park Bike Adventure

• 3 Reviews
• Experience Chicago like never before on this guided, 3-hour bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city’s beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the breathtaking Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory and much more. The use of a bike and helmet is included.
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Chicago North Side Tour

• 3 Reviews
• 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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Chicago Grand Half-Day Tour

• 344 Reviews
• 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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Chicago Architectural Aficionados Bus Tour

• 1 Review
• Get an overview of Chicago's famous architectural history on this 3.5-hour bus tour. Learn about the city's history through your guide's history, from its founding to the present. Stops include the Loop, Mies van der Rohe's IIT campus, Frank Lloyd Wright's Robie House, and the Museum Campus.
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Cultural Mile Walking Tour of Chicago

• 1 Review
• Discover the sights and sounds of Chicago’s various cultural scenes on a 2-hour walking tour. The 1.5-mile route covers music, literature, art, and architecture within the Windy City. Hear insider stories about Chicago's cultural movements and visit little-known locations linked to iconic artists.  Be sure to have your camera ready for the pièce de résistance, the Tiffany stained glass dome at the Chicago Cultural Center.
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Chicago Film Tour

• 50 Reviews
• Take a film-lover's exploration of the Windy City during this 2-hour Chicago movie tour. Whether you're a movie die-hard or just looking for a unique way to explore Chicago, this tour offers a 30 mile (48km) trip by air-conditioned coach past the locations where movies such as Ferris Bueller's Day Off, The Dark Knight and Transformers 3 were filmed. In addition to seeing the filming locations, you'll also have a chance to visit iconic Chicago neighborhoods including Lincoln Park, Wrigleyville, the Gold Coast and Old Town among others. This Chicago film tour also includes a guide.
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Prison Break Escape Room in Chicago

• Bring your own group to River North in Chicago to play the Prison Escape Game. Using creativity and teamwork, work to solve a series of clues within one hour in order to escape before your time runs out. Perfect for groups of work colleagues, friends, and family.
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Chicago Lakefront and Museum Campus Segway Tour

• 10 Reviews
• Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths and rose gardens of Grant Park to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
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NEW TO VIATOR

Urban Sketching Downtown Chicago with a Watercolor Artist

• Spend a morning or afternoon observing Chicago’s iconic urban landscape as you work with a local artist to create your own urban sketch of the city. Learn professional techniques working with pencil, pen, and watercolor, and let your inner artist out onto the page. Explore the city, working inside or outside depending on the season, and go home with photo documentation of your work including photos you sketching in the city and with your final work of art. This tour is Ideal for budding or experienced artists interested in seeing Chicago in a different light and connecting with the urban world in an artistic way.
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Self-Guided Chicago Scavenger Hunt

• Chicago holds many treasures, but this experience helps you uncover the truth--the whole city is a gem. Guide yourself through the clues as you learn about the history of the city and its people. This Chicago scavenger hunt is a fun way to get oriented if you are new to the city, or challenge yourself to go deeper if you already know your way around.
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Self-Guided Key West Scavenger Hunt

• Explore Key West at your own pace during a self-guided scavenger hunt—a great alternative to traditional guided tours. Using only your smart phone, you’ll race against the clock to solve a series of clues while learning fun facts about the city. No set start time is required, so you can easily fit this tour into your schedule. When you’re ready to begin, simply click on a launch code and head to the starting line.
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Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

• 102 Reviews
• 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.
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