Chicago Tours, Tickets, Activities & Things To Do

Chicago Architecture River Cruise

• 2,451 Reviews
• Cruise down the Chicago River to see the city's famous architecture on this 75-minute tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like the Aon Center, the Wrigley Building and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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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 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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Chicago Architectural River Cruise

• 136 Reviews
• See the towers, piers and iconic landmarks along the Chicago River on a 90-minute architectural tour through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.
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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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Big Bus Chicago Hop-On Hop-Off Tour

• 99 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 like the John Hancock Center, 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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SPECIAL OFFER

Skydeck Chicago Admission

• 593 Reviews
• Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower) with this pre-paid admission ticket. From the highest point in the city, look out on Chicago's skyline for panoramic views of the sprawling Windy City. Peruse the interactive displays and exhibits showcasing Chicago's history, which are geared toward curious learners of all ages. Then walk out on to the Ledge, a glass balcony that allows views of Navy Pier and Wrigley Field from one of the world's tallest buildings, standing 1,353 feet (412.4 meters) tall.
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Lake Michigan and Chicago River Architecture Cruise by Speedboat

• 158 Reviews
• Discover Chicago's world-renowned architecture during this 75-minute tour. Board a comfortable river boat for a cruise on the Chicago River, viewing landmarks like the Willis Tower and the Tribune Tower while listening to engaging commentary from your guide. Then board a speedboat for an exciting ride up the shore of Lake Michigan for views of Grant Park, the Chicago Harbor and the Museum Campus.
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Lake Michigan Sightseeing Cruise

• 84 Reviews
• Take in superlative-worthy views of the beautiful Chicago lakefront and its many landmarks during this 40-minute Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's iconic skyline from a unique perspective. Along the way you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch, along or grab a drink at the on-board bar, during your ride.
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Spirit of Chicago Sunset Dinner Cruise with Buffet

• 81 Reviews
• Make your evening in Chicago one to remember with this 3-hour luxury sunset cruise featuring dinner, sightseeing and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ who will mix up a selection of dance favorites.
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SPECIAL OFFER

Chicago City Hop-on Hop-off Tour

• 920 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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Gangsters and Ghosts Tour in Chicago

• 6 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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SPECIAL OFFER

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.
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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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SPECIAL OFFER

Chicago CityPASS

• 262 Reviews
• Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS. This easy-to-carry booklet grants you free entry into top-tier sights including the Shedd Aquarium, Field Museum, Art Institute of Chicago, Adler Planetarium, Skydeck Chicago, Museum of Science and Industry and 360 Chicago (John Hancock Observatory). Plus enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.
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SPECIAL OFFER

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 Grand Half-Day Tour

• 334 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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360 Chicago Observation Deck (formerly John Hancock Observatory) Admission

• 96 Reviews
• Tower above the Windy City’s world-famous skyline with admission to 360 Chicago (John Hancock Observatory). Ascend 94 stories to the observation deck of one of the tallest buildings in North America aboard its lightning-fast elevator. Then check out bird’s-eye views of landmarks like the famous Willis (Sears) Tower and the lakefront shoreline, and enjoy a variety of interactive touch screens and educational exhibits on site. Upgrade to the Sun and Stars package for two visits to the observation deck within 48 hours. With mobile tickets, simply scan your phone for direct entry into 360 Chicago.
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Chicago Odyssey Dinner Cruise

• 43 Reviews
• Take a 2.5-3 hour gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and John Hancock building, plus musical entertainment provided by the on-board DJ.
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Tommy Gun's Garage Dinner and Show

• 153 Reviews
• Transport yourself back in time to Chicago’s roaring twenties at Tommy Gun’s Garage, a unique speakeasy dinner show in the Windy City. Say the password at the front door and then step into an era of mob guys and flappers, Broadway tunes by Cole Porter and George Gershwin and lively dances like the Charleston. This gut-busting show, full of song, dance and audience participation, is sure to please.
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SPECIAL OFFER

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 Architecture Fireworks Cruise

• 6 Reviews
• Take advantage of a rare chance to experience Chicago’s illuminated skyline beneath a fantastic fireworks display. This 90-minute cruise, offered on Wednesday and Saturday evenings all summer, takes you past more than 40 significant works of architecture like the Wrigley Building, Chicago Tribune Tower, John Hancock Center, and more. Your expert guide shares each building’s story, and the cruise concludes with a stunning view of the fireworks from Navy Pier.
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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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SPECIAL OFFER

Chicago Premiere Helicopter Tour

• Travel like a VIP on this premier helicopter tour over Chicago. The adventure begins at Vertiport Chicago, the city’s only downtown heliport. After a walk down a red carpet and a commemorative photo opp (available for purchase and download later), board an Enstrom 480B helicopter with windows on the top, sides, and bottom for unobstructed views of the city below. See Millennium Park, Willis Tower, the Magnificent Mile, and more from an exciting, new perspective. 
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