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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 2,37,670 reviews and posted 52,636 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
Everyone was friendly and helpful. They informed me very early when my room was ready since we arrived very early. The room is small but that was expected. Bathrooms are very...
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Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
My husband and I spent three nights at this hotel in late February when we were in Chicago for a wedding. I understand the hotel was built as a condominium but the units were not...
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Build your budget package
University Club of Chicago
University Club of Chicago
“My favorite!” 05/05/2017
We have been members for a long time and try to get to Chicago as often as possible. We always stay here. This club feels like we are coming home. The guest rooms are nicely...
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Cheap Flights to Chicago
All Washington to Chicago (WAS-CHI) fares found by travellers in the past 72 hours*
Jun
US$ 93 round trip
Jul
US$ 129 round trip
Aug
US$ 129 round trip
†  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.