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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 115,540 reviews and posted 22,306 candid photos for Chicago hotels. Book your Chicago vacation today!
Build your family-friendly package
Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
If you are looking for beautiful, gracious accommodations in the heart of Chicago and the Gold Coast, this is the place. Superb space, outstanding service, great fitness facility...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Langham, Chicago
The Langham, Chicago
My husband and I celebrated our anniversary in one of the lovely appointed rooms. We spent the early evening hours in the lounge sipping cocktails and noshing while overlooking...
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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...
1. Find your perfect hotel
2. Find the right flight
Cheap Flights to Chicago
All Washington to Chicago (WAS-CHI) fares found by travelers in the past 72 hours*
Sep
$105 round trip
Oct
$105 round trip
Nov
$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.