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Don’t Miss These Must-Do Activities in Chicago
Poet Carl Sandburg famously described Chicago as “the City of the Big Shoulders,” and it’s true that this city has extraordinary breadth. Home to record-breaking skyscrapers and enviable lakefront views, world-class museums and dynamite restaurants, a buzzing downtown and historical neighborhoods packed with charm, Chicago is an utterly unique study in contrasts. Whether you wish to admire its architecture from the water’s edge, ascend to the top of one of the Western Hemisphere’s highest buildings, learn about the city’s sordid Prohibition dealings, or admire priceless canvases, this Midwestern powerhouse serves up a dazzling range of entertainment and sightseeing possibilities, no matter your interests. To help you narrow down the options, browse this collection of must-do activities—and get ready to make the most of your Windy City excursion.
7 Tours and Activities
Chicago Architecture River Cruise
8628
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, 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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From
$46.87
From
$46.87
Big Bus Chicago Hop-On Hop-Off Tour
1155
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 several 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 audio commentary onboard gives you insight into the city's colorful history.
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From
$44.99
From
$44.99
Lake Michigan Sightseeing Cruise
462
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's 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 or grab a drink at the onboard bar, during your ride.
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From
$28.34
From
$28.34
Chicago Crime and Mob Bus Tour
1535
Explore Chicago's gangster past on this 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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From
$46.00
From
$46.00
360 CHICAGO Observation Deck Admission (Hancock Center)
332
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 educational exhibits on site.
Upgrade your ticket to include TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. Or, choose 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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From
$30.00
From
$30.00
Bike Tour of Chicago's Lakefront Neighborhoods
169
Pedal past the lakefront neighborhoods of Chicago's North Side on this 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.
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From
$54.99
From
$54.99
Chicago Walking Tour: Art Deco Skyscrapers Loop
90
Admire the incredible façades and intricate interiors of the Windy City's 1920s art deco and art moderne buildings during this architecture walking tour of Chicago. Uncover the history of Chicago art deco architectural along with the city's influential role in the development of this iconic artistic style, as you get an up close and personal look at its wealth of gorgeous period buildings. This art deco Chicago walking tour also includes a certified guide.
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From
$30.00
From
$30.00
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