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Chicago flight deals
Chicago Vacations - Expedia offers the best Chicago Vacation Packages and information on Chicago Getaways.
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Save with Flight + Hotel
In 2008, Expedia customers worldwide saved $248 million just by booking Flight + Hotel together instead of separately.
Chicago featured vacations
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Chicago: Save up to 40%
Get 40% off 4+ nights or 30% off 3 nights! Savor Gold Coast refinement at this intimate boutique-style hotel near Magnificent Mile shopping and Lake Michigan.
Air + 3 nights at Millennium Knickerbocker from $522

Chicago vacation packages
Save 50% in the Windy City
Budget-conscious travelers rejoice! This conveniently-located hotel features easy access to the airport as well as big savings.
Air + 3 nights at Holiday Inn O'Hare from $454
More Chicago vacation deals
Embassy Suites - Chicago O'Hare - Rosemont
Embassy Suites - Chicago O'Hare - Rosemont
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Las VegasChicago: Air + 3 nights' hotel$507
Find more Chicago vacation deals
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
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Las VegasChicago: Air + 3 nights' hotel$527
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Hilton Suites Chicago Magnificent Mile
Hilton Suites Chicago Magnificent Mile
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Las VegasChicago: Air + 3 nights' hotel$514
Find more Chicago vacation deals
Activities, attractions, and more What's this?
Make a great trip even better—add these activities to your Chicago vacation:
Chicago attractionsChicago Gran Tour and Hancock Tower
from $50
Chicago attractionsField Museum
from $22
Chicago attractionsChicago Segway tour
from $65
See more Hard-To-Getsm tickets from RazorGator—sports, concerts, theater!
Best of Chicago
Experts’ top picks: Hotels, theme parks, eats, more.
See top picks
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