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Chicago All Inclusive Resorts & Pre-Packaged Vacations

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Chicago Vacation Guide

From the Loop and Lake Michigan to baseball and blues, Chicago is a city that simply screams American style.

The Second City
Though Los Angeles is undeniably the country's second-largest spot, Chicago holds a special place in the collective heart of the United States. Since its founding in the early 19th century, this take-no-prisoners town has played host to gangsters and legends, presidents and pioneers, and some of the most iconic jazz and blues spots this side of the Mississippi. It's almost symbolic of the nation's fierce independence; despite the glossy updates to its shopping strips and tourist attractions, Chicago still operates with a bold, brash ethos.

A World-Class Destination
Believe the hype: All-inclusive packages for Chicago IL are every bit as exciting as those in Los Angeles and New York. The landscape may be different — Chicago's skyline tends toward the futuristic, for instance, and its upscale districts are uniquely vibrant — but the cultural attractions are on par with the world's best. This is, above all, a powerhouse of a city, and that no-holds-barred attitude is evident in everything from the art museums to the cutting-edge restaurants.

Beyond the Breeze
Of course, there's a reason they call it the Windy City. Thanks to its position on Lake Michigan, this metropolis is subject to a relatively constant breeze. The seasons here are clearly defined with scorching summers and freezing winters, so you'll generally find the most comfortable temps in the transitional periods. Don't discount those high-season months however: Some of the best packages and cheap deals are available on hotels in Chicago when the mercury moves into the extremes.

Top Things to See and Do
Unless you're staying for several weeks, you'll need a tightly coordinated itinerary to hit the hottest sights. Lincoln Park is the best spot for bustling beaches and gorgeous gardens, and its associated Lincoln Park Zoo is designed to make any animal lover swoon. Wrigley Field is a must for baseball fans, but head straight for Navy Pier when the sun goes down. The city's most effervescent clubs and restaurants are situated in the area, and you can easily head to the North Side for its iconic blues joints. If you rent a car in Chicago, set it aside for your downtown adventures. The L is more than sufficient.

Chicago All-Inclusive Deals, Discounts, and More
Before you make a beeline for the city's borders, browse the travel tools at Expedia to find the latest holiday packages combining your accommodations and flight deals to Chicago. Chi-Town getaways have never looked so sweet.

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