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    Chicago Holiday Packages

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    Chicago
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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 252,981 reviews and posted 50,013 candid photos for Chicago hotels. Book your Chicago vacation today!
    Or build your own Chicago holiday package
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    The Talbott Hotel
    The Talbott Hotel
    4.5 of 5 bubbles 2,868 reviews
    “Wonderful hotel” 24/09/2017
    Fantastic hotel in the heart of Chicago. Wonderful and friendly staff. Roberta, in housekeeping, was outstanding and went out of her way to make sure we had everything we needed...
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    The Guesthouse Hotel
    The Guesthouse Hotel
    5.0 of 5 bubbles 323 reviews
    “Absolutely A+ experience!” 30/08/2017
    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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    University Club of Chicago
    University Club of Chicago
    4.5 of 5 bubbles 77 reviews
    “Great Location Special Place” 06/09/2017
    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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    Cheap Flights to Chicago
    All Washington to Chicago (WAS-CHI) fares found by travellers in the past 72 hours*†
    Oct
    US$79 return
    Nov
    US$79 return
    Dec
    US$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.