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Chicago Holiday Packages

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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 234,159 reviews and posted 51,503 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
The Talbot was a wonderful hotel. We booked a suite deal that allowed us to book a two room suite for a very affordable rate. The hotel was in the center of everything and the...
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2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
“LOVED IT!” 24/04/2017
Such an amazing place to stay. Located in Andersonville, a great neighborhood by the way, with plenty of restaurants & cool shops. Stayed at Guesthouse as we were seeing a show...
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2. Find the right flight
Build your budget package
University Club of Chicago
University Club of Chicago
We stayed at the University Club for a family reunion weekend. It felt like we were entering Hogwarts. The guest rooms were large and comfortable and the staff was courteous...
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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*
May
US$93 return
Jun
US$106 return
Jul
US$127 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.