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 | All Chicago Tours
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Chicago Crime and Mob Bus Tour
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
$45.00
From
$45.00
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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 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 live commentary onboard gives you insight into the city's colorful history.
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From
$26.10
From
$26.10
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
Chicago Architecture River Cruise
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
$38.85
From
$38.85
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
360 CHICAGO Observation Deck Admission (Hancock Center)
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
$25.00
From
$25.00
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Chicago Grand Half-Day Bus 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.
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From
$52.95
From
$52.95
Transportation vehicles regularly sanitized
Lake Michigan Sightseeing Cruise
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 or grab a drink at the onboard bar, during your ride.
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From
$25.07
From
$25.07
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
Bike Tour of Chicago's Lakefront Neighborhoods
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
$49.99
From
$49.99
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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