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Visiting Chicago for the First Time? Here's What to See and Do


Visiting Chicago for the First Time? Here's What to See and Do
Hi, I'm Claire!

Claire Bullen is an award-winning food, drinks, and travel writer and editor who has lived and worked in Chicago, Philadelphia, New York, Paris, and London. She is the author of The Beer Lover's Table: Seasonal Recipes and Modern Beer Pairings, and the editor at GoodBeerHunting.com. Her writing has also appeared in Time Out New York, The Daily Meal, Pellicle Magazine, and beyond.

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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.


Head to the top of the Willis Tower

One of Chicago's top landmarks.

Formerly known as the Sears Tower, the Willis Tower is one of the tallest buildings in the Western Hemisphere (for a time, it was the tallest 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.

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Try authentic, Chicago-style pizza

Don't tell the New Yorkers.

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.

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Deep dish pizza is a must-try in Chicago. Photo: Brittany Hosea-Small / Viator

Admire the masterpieces at the Art Institute of Chicago

Even non-art lovers will enjoy.

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.

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See the city from the water

Architecture cruises are perennially popular.

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.

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Chicago's architecture boat tours are popular for a reason. Photo: Brittany Hosea-Small / Viator

Discover the city's prohibition history

The Windy City has a lively past.

Chicago was once frequented by infamous gangsters, including 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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Explore Millennium Park's art and gardens

Enjoy urban greenery.

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 landmark Cloud Gate (better known as "The Bean”). Explore on foot, or speed along on a bike or Segway tour.

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It's tough to miss the "Bean," Chicago's landmark sculpture. Photo: Sam Girton / Viator

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Hi, I'm Claire!

Claire Bullen is an award-winning food, drinks, and travel writer and editor who has lived and worked in Chicago, Philadelphia, New York, Paris, and London. She is the author of The Beer Lover's Table: Seasonal Recipes and Modern Beer Pairings, and the editor at GoodBeerHunting.com. Her writing has also appeared in Time Out New York, The Daily Meal, Pellicle Magazine, and beyond.

Keep exploring
See all Chicago tours
322 tours & tickets
Things to do in Chicago
See all things to do in Chicago
Know Before You Go: Visiting Chicago in Winter
Know Before You Go: Visiting Chicago in Winter