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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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Chicago featured vacations
Chicago vacation packages
Save up to 20% on 2 nights in Chicago
Relax in your own sitting area and save up to 20% on 2+ nights near Chicago's Lakefront and Water Tower Place shopping.
Air + 3 nights at Omni Chicago Hotel from $510

Chicago vacation packages
Winter wonderland savings to 40% in Chicago
Save up to 40% in Chicago on a terrific selection of hotels during the winter wonderland sale in this fascinating Midwest city.
Air + 3 nights at Holiday Inn O'Hare from $367
More Chicago vacation deals
Holiday Inn Select O'Hare Airport
Holiday Inn Select O'Hare Airport
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Las VegasChicago: 3-night air + hotel package$466
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Omni Chicago Hotel
Omni Chicago Hotel
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Las VegasChicago: 3-night air + hotel package$501
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The Palmer House Hilton
The Palmer House Hilton
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Las VegasChicago: 3-night air + hotel package$523
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Activities, attractions, and more What's this?
Make a great trip even better—add these activities to your Chicago vacation:
RazorGator Hard-To-Get ticketsHard-To-Getsm tickets from
RazorGator
Chicago attractionsChicago Grand Tour
from $40
Chicago attractionsMedieval Times Shaumburg
from $53
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
BOOK A TRIP TO CHICAGO
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