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Chicago Hotel + Air Packages

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Build your own Chicago vacation package
Want to book a vacation to Chicago? Whether you're off for a romantic vacation, family trip, or an all-inclusive holiday, Chicago vacation packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect vacation package for Chicago on TripAdvisor by comparing Chicago hotel and flight prices. Travelers like you have written 112,071 reviews and posted 20,808 candid photos for Chicago hotels. Book your Chicago vacation today!
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Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
The Four Seasons Hotel Chicago has all the amenities, location, friendly staff, beautiful views, great bar and restaurant. It is a treat to stay here and you will not be...
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2. Find the right flight
Build your luxury package
The Langham, Chicago
The Langham, Chicago
“Outstanding” 07/13/2014
My wife and I stayed on the Langham Club level and everything was perfect. Checkin was smooth, the room was luxurious and access to The Langham Club Lounge was worth every penny...
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2. Find the right flight
Build your budget package
University Club of Chicago
University Club of Chicago
“Wedding” 07/10/2014
I was in a wedding here so I am not sure what the hotel is like but I can say the food they served was great, although it was lunch, It was also beautiful with all the stained...
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2. Find the right flight
Cheap Flights to Chicago
All Washington to Chicago (WAS-CHI) fares found by travelers in the past 72 hours*
Jul
$168 round trip
Aug
$158 round trip
Sep
$98 round trip
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.