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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 114,704 reviews and posted 21,422 candid photos for Chicago hotels. Book your Chicago vacation today!
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Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
Best hotel on the gold coast (Near north Side of Chicago) Spa was fantastic-had a fantastic massage. Room Service was fast, friendly and delicious and fresh food (Breakfast). Room...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Langham, Chicago
The Langham, Chicago
OMG! what a lovely hotel. My husband and I were doing a mini tour of East America to celebrate our first wedding anniversary. We went from Toronto in Canada down to Milwaukee...
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2. Find the right flight
Build your budget package
University Club of Chicago
University Club of Chicago
We got married at The University Club downtown Chicago late November last year. We were so very happy with the ease of planning (THANK YOU CHARLOTTE!) and the flow of the day...
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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*
Aug
find price round trip
Sep
$105 round trip
Oct
$105 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.