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Welcome to The Windy City
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. Explore
Our 42-hour vacation itineraries are tailored to your interests-- from arts-and-culture escapes to outdoor adventures. Find out how far you can go in just 3 hours-- or less!Read More
Sure, this city has great architecture, museums, and sports venues. But at its heart, Chicago is really a food...Read 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.”
Image Credit: Charles Cook / Getty Images
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.
Image Credit: Ryan McVay / Getty Images
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.
Image Credit: Steve Geer / Getty Images
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.
Image Credit: Phillip Hayson / Getty Images
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.
Image Credit: Chris Pritchard / Getty Images
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.
Image Credit: 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.
Image Credit: Bruce Leighty / Getty Images
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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.
Discover the very best of Chicago.
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