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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 228,906 reviews and posted 51,039 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
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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2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
The Guesthouse Hotel is an immaculate, peaceful, beautifully appointed hotel. The beds are very comfortable and the suites are very spacious. There are many great restaurants...
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2. Find the right flight
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
USD 79 return
Apr
USD 89 return
May
USD 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.