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Chicago Holiday Packages

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Chicago
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Chicago Holiday Packages
Want to book a holiday to Chicago? Whether you're off for a romantic holiday, family trip, or an all-inclusive holiday, Chicago holiday packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect holiday package for Chicago on TripAdvisor by comparing Chicago hotel and flight prices. Travellers like you have written 252,315 reviews and posted 50,449 candid photos for Chicago hotels. Book your Chicago holiday today!
Or build your own Chicago holiday package
Build your family-friendly package
The Talbott Hotel
The Talbott Hotel
We stayed here for 6 nights and loved it. - fantastic location up near the Hancock building end of the magic mile. It's an easy 10-15 min walk down toward the Michigan ave...
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2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
A previous reviewer mentioned that she would give this place 10 stars if she could - I absolutely echo that! I experienced The Guesthouse Hotel in two ways - I threw a party...
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2. Find the right flight
Build your budget package
University Club of Chicago
University Club of Chicago
I had the opportunity to stay at the University Club of Chicago on a recent business trip. A very special place if you have business downtown and appreciate classic...
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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*
Oct
USD 79 return
Nov
USD 79 return
Dec
USD 79 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.