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Build your own trip.
Choose the flight that’s just right for you, or add the convenience of a rental car. You'll always find special low rates and plenty of choices—so it's easy to plan the perfect trip.
Chicago air deals
departure city
destination city
from
New York
Chicago
$175
Los Angeles
Chicago
$287
Los Angeles
Chicago
$295
Boston
Chicago
$179
Boston
Chicago
$179
Chicago car deals
supplier
offer
from
Dollar
compact cars (weekday rate)
$33
Dollar
economy cars (weekday rate)
$33
Dollar
midsize cars (weekday rate)
$44
Save with Flight + Hotel
In 2008, Expedia customers worldwide saved $248 million just by booking Flight + Hotel together instead of separately.
Activities, attractions, and more
What's this?
Make a great trip even better—add these activities to your Chicago vacation:
Made in Chicago Shopping Tour
from
$41
Chicago CityPass
from
$59
Chicago Segway Tour
from
$65
BOOK A TRIP TO CHICAGO
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flight+hotel
flight+hotel+car
Departing From:
Depart:
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morning
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anytime
Going to:
Chicago
Return:
Nov
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morning
noon
evening
anytime
Rooms:
Adults:
Seniors:
Children:
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