Top Chicago Tours & Sightseeing

Chicago Crime and Mob Tour

• 374 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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Big Bus Chicago Hop-On Hop-Off Tour

• 101 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 Explorer Pass

• 169 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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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 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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Gangsters and Ghosts Tour in Chicago

• 9 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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Chicago City Minibus Tour with Optional Architecture River Cruise

• 95 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. 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 City Hop-on Hop-off Tour

• 921 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 Grand Half-Day Tour

• 335 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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Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

• 100 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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Chicago Segway Tour

• 210 Reviews
• 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.
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Haunted Chicago Segway Tour

• 15 Reviews
• Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide for 2 hours as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.
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Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

• 81 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 Night Crimes Tour

• 3 Reviews
• 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.
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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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Private Chicago Highlights Driving Tour

• 3 Reviews
• 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.
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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. 
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Urban Sketching Downtown Chicago with a Watercolor Artist

• We will be sketching the urban landscape of downtown Chicago using pencil, pen, and watercolors. During this two and a half hour experience you will learn the basics of Urban Sketching and complete at least one piece of art work. I'll show you how to let your guard down and your inner artist out. During the cooler days, if it's raining, or snowing we'll sketch inside at one of the many Chicago architectural gems.
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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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Gold Rush Escape Room in Chicago

• Experience the immersive thrill of the Gold Rush Escape Game. Hunt for the hidden treasure of a missing Northern California gold prospector as the mob closes in on your loot. Rely on expert instincts, teamwork and determination to find the stash before your enemy does. Complete your mission and escape within one hour. 
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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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Alleys of Chicago North Loop Photo Tour

• 2 Reviews
• You may never have thought of the back alleys of Chicago’s North Loop as particularly photogenic. This small group tour will change your perceptions by helping you find the overlooked interesting shots and scenes that make for unforgettable photographs. You don’t have to have a fancy camera to participate, just a mind that’s open to the art in unexpected places.
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Chicago Film Tour

• 49 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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Best of Chicago Tour Including a Deep-Dish Pizza

• 5 Reviews
• Tour Chicago's sights aboard a luxury coach and enjoy some Chicago-style deep-dish pizza on this 5.5-hour guided tour. Visit sites like the Hancock Tower, the Lincoln Park Conservatory and the Loop. Pass through neighborhoods such as Wrigleyville, Lincoln Park and Gold Coast. Top off your tour with a visit to one of Chicago's most popular pizza restaurants to sample the famous Chicago-style deep dish pizza.
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