Chicago is a city with an appetite—for food, of course, but also for design, history, and culture. Come here to marvel at the cutting-edge architecture or take in the gorgeous views of Lake Michigan; to spend a day cheering with baseball fans and a night laughing at a comedy show; to shop, to visit renowned institutions like the Field Museum and the Adler Planetarium, and to experience the legendary blues scene. To do all this, you'll need nourishment: taste deep-dish pizza, piled-high hot dogs, Italian beef sandwiches, and more.
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Things You Can’t Miss
Contemplate the deep thoughts of the anonymous diners of one of America’s most important and timeless paintings: Edward Hopper’s “Nighthawks.”
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The Map Room is a great, friendly bar with 200 types of beer representing 36 brewing styles, and a proper glass is always used for each style of beer.
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Chicago is an architectural showstopper, and I love to stay downtown to be surrounded by the swirl of art deco buildings and gleaming 20th-century towers.
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Gaze at the reflected city skyline in Anish Kapoor's iconic, three-story sculpture, Cloud Gate, at this recent addition to Chicago's downtown area.
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For views as spectacular as those at the Willis Tower, and lines about half the size, this architectural gem in Chicago's northeast is a must visit.
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Logan Square's sweeping boulevards make for some of Chicago’s best walking. Jump on the Blue Line and discover all that this neighborhood has to offer.
Stevegeer / iStockphoto
In the mood for comedy? Take the Brown Line over to Old Town for a night of laughs at Second City Theater – home of Chicago improv for over 50 years.
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Shared Trips to this Destination
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Must Reads Before You Go
Chicago vacation travel guide and tour information including highlights such as the Brookfield Zoo, Museum of Science and Industry, and Steppenwolf.