Chicago, Illinois - Vacation Packages

The United State’s third largest city is also known as the ‘windiest’ - not because of the brisk air (although there is plenty of that, too) but for the old political machines that used to run it. Middle America’s melting pot started off as a trading post on Lake Michigan, although it’s hard to picture to city without its statuesque buildings, including the tallest one in the United States, the Sears Tower, and its vibrant blues and nightlife scene.

During the day, the city is best explored on foot and on the L, the elevated train system. On Michigan Avenue - also known as the Magnificant Mile - open up your pocketbooks for a day of splurge shopping. Or, if window browsing is more your thing, look around at the brilliant skyscrapers and famous buildings such as the Tribune Tower and the Wrigley Chewing Gum Headquarters. Then head to Navy Pier for some carnival-esque shopping and rides.

If the buildings get to be too much, go east young (wo)man and walk, jog or bike along the shores of massive Lake Michigan. In the summer, grab for suit for some sunbathing and maybe a brief dip. When your day is over, head back into the city for drinks at the top of one of its tallest buildings, the John Hancock, and then feast at one of the thousands of restaurants.

Why go to Chicago, Illinois?

• Deep-dish pizza
• Cheer for the Cubs in the right field bleachers of historic Wrigley Field
• This is the home of the blues
• Deep dish pizza
• Incredible architecture in the downtown loop
• Shop till you drop on Madison Avenue, the Magnificent Mile
• See some of the best museums in the world on free days
• Rollerblade along the banks of Lake Michigan
• Stuff yourself silly at the taste of Chicago
• Tailgate party!… then freeze your butt off at a Bears game in January
• Did we mention deep dish pizza?

For more on Windy City, check out the Chicago Travel Guide on BootsnAll.

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