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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 2,60,773 reviews and posted 51,201 candid photos for Chicago hotels. Book your Chicago holiday today!
Or build your own Chicago holiday package
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The Talbott Hotel
The Talbott Hotel
Stayed for a 10 days long work trip. The room was big and I loved the less-is-more- design in my room. Not much noise from the street at all (stayed on 4th floor), friendly and...
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Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
What a sweet place to stay in Chicago! It is in an interesting neighborhood, the apartments are nicely decorated and comfortable, parking is secure, and they have created a great...
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Build your budget package
Carlton Inn Midway
Carlton Inn Midway
I was headed to Chicago for a conference and spent a week at this property. I couldn't afford a hotel in the city so I opted for this hotel for its value and proximity to the...
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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*
Dec
US$ 97 round trip
Jan
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Feb
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†  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.