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How to Tackle Chicago as a First Timer

How to Tackle Chicago as a First Timer

Planning a first-time visit to the Windy City? Home to extraordinary skyscrapers and pretty parks, world-class museums and top-notch bites, Chicago has something for everyone. To help you make the most of your first time in town, we’ve picked the city’s unmissable highlights—here’s what to add to your itinerary.

Ascend to the Top of the Willis Tower

Formerly known as the Sears Tower, the Willis Tower is one of the tallest buildings in the Western Hemisphere (for a time, it was No. 1 in the world). There are few more classic Chicago experiences than taking a lightning-fast elevator up to its Skydeck, where you can admire extraordinary city panoramas. Book early morning VIP tickets to see it sans crowds—and step onto the glassed-in ledge if you dare.

Explore Millennium Park’s Art and Gardens

An oasis of green amidst the Loop’s soaring skyscrapers, busy shopping streets, and rumbling L trains, Millennium Park offers a wealth of cultural and aesthetic highlights. A top Windy City attraction since 2004, the park comprises gardens, event spaces, and public artworks—including Anish Kapoor’s landmarkCloud Gate (better known as “The Bean”). Explore on foot, or speed along on a bike or Segway tour.

Try Authentic, Chicago-Style Pizza

Chicagoans take their pizza seriously—and whether you’ve got a hankering for the classic deep-dish offerings or want to try the city’s thin-crust alternatives, pizza-centric walking tours offer the perfect culinary survey. 

See the City—and Its Architecture—by Boat

One of the niftiest ways to explore downtown Chicago—and see many of its top landmarks in just an hour or two? Hop aboard a boat tour. As you wend your way along the Chicago River, spy Windy City architectural icons, and learn how they were built. Alternatively, trawl the waters of Lake Michigan to discover Chicago’s own inland sea.

Visit the Masterpieces at the Art Institute of Chicago

Among the city’s top museums, the Art Institute of Chicago boasts a sprawling collection, which encompasses some 300,000 objects. Make like Ferris Bueller and get up close and personal with its masterpieces: Artworks by Georgia O’Keeffe, Pablo Picasso, Marc Chagall, Georges Seurat, and Edward Hopper number among its highlights.

Discover the Windy City’s Prohibition History

Chicago was once frequented by infamous gangsters the likes of Al Capone, and the advent of Prohibition in the 1920s saw its number of speakeasies—and sordid happenings—soar. Embark on a one-of-a-kind history tour to learn about this memorable moment in Chicago’s past, and even drop by the city’s trendy, modern-day speakeasies to indulge your inner flapper.

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6 Tours and Activities | All Chicago Tours

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Chicago Crime and Mob Tour

Chicago Crime and Mob Tour

star-4
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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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
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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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$38.85
From
$38.85
Taking safety measures

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
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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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$27.00
From
$27.00
Taking safety measures

Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

star-5
Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$45.99
From
$45.99
Taking safety measures

Famous Tastes of Chicago Food Tour

Famous Tastes of Chicago Food Tour

star-4.5
Discover Chicago’s food, history, architecture and culture on this 3-hour, small-group walking tour. Try six of the Windy City’s quintessential staples from local restaurants and specialty food shops like Pizano’s Pizza and the Berghoff, the oldest family run-establishment in Chicago. Taste local favorites including deep-dish pizza,  Chicago Italian Beef Sandwich and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural and architectural components that make up this legendary town.
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  • 3 hours
From
$0.00
From
$0.00

2-Hour History of Chicago Architecture and Art Segway Tour

2-Hour History of Chicago Architecture and Art Segway Tour

star-5
Explore the art and architectural highlights of Chicago on a Segway during this guided tour. This family-friendly tour takes visitors by the outdoor sculptures, landmark buildings, and iconic skyline of the city. Accompanied by educational and informative commentary, this city tour saves you from hours of walking and lets you see all of Chicago's top art and architectural attractions in one tour.
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  • 2 hours
  • Free Cancellation
From
$75.10
From
$75.10