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Chicago Holiday Packages

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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 228,773 reviews and posted 50,973 candid photos for Chicago hotels. Book your Chicago vacation today!
Or build your own Chicago holiday package
Build your family-friendly package
The Talbott Hotel
The Talbott Hotel
Really great hotel. Absolutely fantastic. In the centre of Chicago - not far away from shopping malls and great restaurants. Concierge was amazing. Was looking for various...
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Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
This hotel definitely made me feel at home, which was perfect for my wife and 1 year old. The service was great, and all of the staff was very helpful and friendly. The room was...
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Build your budget package
Carlton Inn Midway
Carlton Inn Midway
Located pretty close to a metro station, so you can leave your car at the hotel, when you go downtown Chitown. Very good Italian restaurant close by! Breakfast room is bright and...
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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*
Mar
US$79 return
Apr
US$89 return
May
US$101 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.