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Top Chicago Sights

  Published: Oct 11, 2016

  Updated: Oct 11, 2016

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Frommers.com Community
By Laura Tiebert

Frank Sinatra once proclaimed Chicago his kind of town. It's mine, as well. Awaiting you in the Windy City are new discoveries and favorite places you'll want to visit again and again, from riding the "El" to singing along with the crowds at Wrigley Field's seventh-inning stretch. Here are nine some quintessential Chicago experiences that just might become part of your family's vacation lore. They may make Chicago your kind of town, too.

Photo Caption: Navy Pier, Chicago, IL. Photo by Jessica Johnston/Frommers.com Community

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Take Yourself Out to the Ballgame at Wrigley Field

Our historic ballpark, Wrigley Field, approaches perfection with its ivy-covered walls, hand-operated scoreboard, and view of the jade colored, glassy waters of Lake Michigan from the upper decks. Now that lights have been installed, the Cubs play night games, but Wrigley is still best experienced on a summer afternoon, when you'll be surrounded by plenty of natives playing hooky from work -- a Windy City tradition.

Photo Caption: Wrigley Field, Chicago, IL. Photo by RabidUnicorn/Frommers.com Community.

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Take a Ride on our Famous "El" Train

Our "El" train (elevated train) is not only the least expensive ride in town, it's an experience that can be had only in Chicago. For the best views, board the Brown Line at Washington/Wells, and ride it around the Loop through the canyons of office buildings (you'll be close enough to peer into some of them). It'll take less than 30 minutes of your touring time, and kids love it.

Photo Caption: The El train, Chicago, IL. Photo by kganno2/Frommers.com Community.

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Take in World Class Art

Marvel at the intricate pointillism of Seurat's A Sunday on La Grande Jatte and other masterpieces at Chicago's grande dame of museums, the Art Institute of Chicago. You'll find Seurat's work in the renowned Impressionist collection, which also features one of the world's largest collections of Monet paintings. Your second stop should be the collections of European and American contemporary art, home to works by Picasso, Matisse, Dalí, Pollock, and Warhol.

Photo Caption: Art Institute of Chicago. Photo by JWbost/Frommers.com Community

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Stroll the Lakefront and Ogle our Inland Ocean

Chicago's forefathers had the foresight to keep the city's 29 miles (47km) of lakefront free and clear of development. As a result, you can bike, skate, jog, or walk along Lake Michigan and enjoy a chain of parks that includes Chicago's signature Lincoln Park and Grant Park.

Photo Caption: Chicago from the Lake. Photo by ksktmfrl/Frommers.com Community

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Admire our Renowned Skyline on a Cruise Along the Chicago River

The best way to get a perspective on Chicago's history and learn about the dramatic buildings that form the city's skyline is to take an architecture boat tour. Some of the best are run by the Chicago Architecture Foundation, covering some 40 buildings with entertaining and enlightening narrative from an army of well-versed docents.

Photo Caption: Boat cruise on the Chicago River, Chicago, IL. Photo by Bubba/Frommers.com Community.

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Grip the Edge of Your Seat at a Chicago Theater Performance

Whether you choose a production by the Steppenwolf Theatre Company, Goodman Theatre, or a smaller venue such as Victory Gardens Theatre, don't miss a chance to see what might be the next big hit to move to Broadway.

Photo Caption: Chicago Theatre, Chicago, IL. Photo by Gruezi/Frommers.com Community.

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Explore Hyde Park's Gothic Quadrangle and Magnificent Mansions

Home to the University of Chicago, with its 73 Nobel laureates, intimidating buildings with Gothic spires, and hallowed academic halls, Hyde Park is sure to impress. Off-campus, Hyde Park is an integrated, cosmopolitan neighborhood that's home to one of Frank Lloyd Wright's finest works, the Robie House.

Photo Caption: Frank Lloyd Wright's Robie House in Chicago's Hyde Park neighborhood.

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Get Wet at the World's Largest Indoor Aquarium

The John G. Shedd Aquarium is a city treasure. Don't miss the Oceanarium, which re-creates a Pacific Northwest coastal environment and features a wall of windows that reveals the lake outside and creates the illusion of one uninterrupted expanse of sea (that's where you'll find those baby belugas).

Photo Caption: John G. Shedd Aquarium, Chicago, IL. Photo by not_the_stig/Frommers.com Community.

Jérémie Souteyrat

Interact With the Sculpture at the City's Newest Urban Showpiece