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Introduction to Chicago |Maps

Resources: Neighborhoods | Restaurants | Shopping | Travel Tools

Your Chicago Vacation Guide

"Chicago is one town that won't let you down," Sinatra first sang in the '60s. And it's still true.

Whether your interests are cultural or culinary, musical or historical, high-end or down-home, the Windy City delivers.

Let Orbitz help plan your ideal Chicago vacation:

Get hotel recommendations by interest.
Find events and festivals.
See Chicago hotel deals, including exclusive offers.

Chicago Featured Interests

Chicago Featured Hotels

Events and Festivals

Date

Event Details

Now - September 4

Millennium Park Family Fun Festival
Enjoy family-friendly activities, concerts and performers in the heart of downtown Chicago's Millennium Park

September 4 - 6

Chicago Jazz Festival
Spend Labor Day weekend at one of Chicago's longest running lakefront festivals. The Chicago Jazz Festival features diverse local, national and international musicians.

October 3 - 4

Chicago Country Music Festival
Enjoy three stages of country music featuring top names in talent. New features this year include a dance tent and a Kids Corral.

October 22 - 25

Fashion Focus Chicago
Step out in style at this 5^th annual celebration of Chicago fashion designers and the fashion industry. See runway shows in Millennium Park and take advantage of special shopping discounts.

October 1 - 31

Chicagoween
Halloween is more than a day in Chicago; it's an entire season! Participate in scary happenings throughout the city and its parks.