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Chicago Holiday Packages

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Chicago Holiday Packages
Want to book a vacation to Chicago? Whether you are 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 225,569 reviews and posted 50,408 candid photos for Chicago hotels. Book your Chicago vacation today!
Or build your own Chicago holiday package
Build your family-friendly package
The Talbott Hotel
The Talbott Hotel
Upon check in we were noticed we were going to be the last guests before the hotel was due to be closed for renovation. The staff and accommodations were very comfortable and...
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Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
This is a fabulous property. The room was outstanding, the employees bright and friendly, and the location was great. The price was good for a Chicago hotel and the optional...
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Build your budget package
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
This hotel is in a great location near downtown and Millennium Park with the Bean sculpture. It's in walking distance from the Art Institute Museum and the Magnificent mile...
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2. Find the right flight
Cheap Flights to Chicago
All Washington to Chicago (WAS-CHI) fares found by travellers in the past 72 hours*
Feb
US$77 return
Mar
US$121 return
Apr
US$149 return
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travellers 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.