Chicago Theatre, Chicago, Illinois (Chicago Convention and Tourism Bureau)

Night skyline of Chicago, Illinois (PhotoDisc)

Aerial view of Chicago, Illinois skyline at dawn (Corbis)

Night skyline of Chicago, Illinois (Brand X)

Magnificent Mile in Chicago, Illinois (Chicago Convention and Tourism Bureau)

Millenium Park, Chicago, Illinois (Chicago Convention and Tourism Bureau)

Water Tower in Chicago, Illinois (Chicago Convention and Tourism Bureau)

Art Institute of Chicago, Illinois (Chicago Convention and Tourism Bureau)

(Hemera/Thinkstock)

Skyline & Chicago's First Lady cruise ship, Chicago, Illinois (Cruise Chicago)

Edward Rothberger

Aerial view of Lake Michigan and skyline of Chicago, Illinois (Corbis)

Buckingham Memorial Fountain, Chicago, Illinois (Brand X)

The Bean sculpture in Millennium Park, Chicago, Illinois (Chicago Convention and Tourism Bureau)

McCormick Place convention center, Chicago, Illinois (Chicago Convention and Tourism Bureau)

Skyline and Soldier Field in Chicago, Illinois (Chicago Convention and Tourism Bureau)

What to do in Chicago

by Elaine Glusac

Chicago’s known for 5,000-calorie deep-dish pizza and colloquialisms surrounding its sports teams (“’da Bears” and “’da Bulls”). But don’t think of the Windy City as only a Midwestern, blue-collar burg. A rich seam of creativity runs through every neighborhood. Chicago invented the skyscraper, and early editions are on display across downtown. Esteemed architect Frank Lloyd Wright made his home in Oak Park. Ornate fountains and modern sculptures dot lakeside Millennium Park. And despite boasting one of the world’s best art museums (the Art Institute), the city’s public art is just as good, with open-air installations such as Anish Kapoor’s Cloud Gate and works by masters including Picasso, Miró, and Chagall. If highbrow isn’t your thing, just hole up in a more intimate venue like The Metro or Goose Island Brewery and toast to ’da Bears.

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Wandering Soles rates Chicago
There is sooo much to do and see in Chicago. Try taking the tour up to the top of the Willis Tower (formely the Sears Tower) and enjoy 360 degree view of the third largest city in the U.S. I think I paid $17 for this tour. Catch the "L" (train) from either O'Hare or Midway airports. Marvel at the impressive architecture of both the old and modern buildings downtown. If it's warm and sunny, enjoy a day at the beach on Lake Michigan. Plus, plenty of fine restaurants to treat your taste buds.
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Fat Paddler rates Chicago
If you want to really see the city, do a kayak tour down the Chicago River. You can do architecture tours, gangster tours or fireworks tours, but regardless of choice seeing the towers of Chi-town from the water at night is just mesmerizing. If water isn't your thing, then head to the Golden Mile for great shopping. Lots of major stores there like the Disney Store, Apple Store, North Face etc. At night there are heaps of clubs, my particular favourite is Kingston Mines, a kicking blues bar that seriously rocks - sit down at one of the bench like tables with a "bucket of beer" and enjoy the show. There's heaps of sport in Chicago as well, if you do get to a game make sure you get a Chicago Dog (sports chillis, celery salt, NO ketchup!).
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Pieter rates Chicago
I really love the outdoor art installations in Chicago. The Chagall mosaic is really captivating. I could spend a lot of time just hanging out down by the waterfront of Lake Michigan. It also has a fantastic St. Patrick's Day celebration--before going, I didn't know there were so many Irish descendants in town. The one place I wasn't crazy about was Navy Pier. It was just touristy and very, very crowded.
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Ossie rates Chicago
There's a great variety of things to see and do in Chicago, plus the food, nightlife, and entertainment scenes are all top-notch. I've been here in both summer and winter and really enjoy wandering amidst the historic skyscrapers and then out into the sudden open expanse of Grant Park and the much-loved Millennium Park. (There's a great water fountain/art installation here in the summer, plus loads of other cool outdoor events.) During summer, it's also a really nice walk along the waterfront to the zoo and neighborhoods around Wrigley Field. I'd definitely recommend going here without an agenda and seeing where the wind blows you (quite literally, sometimes!).
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There is sooo much to do and see in Chicago. Try taking the tour up to the top of the Willis Tower (formely the Sears Tower) and enjoy 360 degree view of the third largest city in the U.S. I think I paid $17 for this tour. Catch the "L" (train) from either O'Hare or Midway airports. Marvel at the impressive architecture of both the old and modern buildings downtown. If it's warm and sunny, enjoy a day at the beach on Lake Michigan. Plus, plenty of fine restaurants to treat your taste buds.
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