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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 224,860 reviews and posted 50,231 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
Stayed there for three nights in August. Superb staff, great welcome and a wonderful (slightly old fashioned) room. Such a change from the usual city hotels. Parking was very...
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2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
You won't find a better place to stay in Chicago. I promise you that. My wife and I traveled from Boston to visit my son and daughter-in-law and our new grandson. I wanted to be...
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2. Find the right flight
Build your budget package
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
Stayed here with some colleagues for a conference in Chicago. The room was small, but clean and up to date. The lobby was gorgeous and the continental breakfast was delicious with...
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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*
Feb
US$73 return
Mar
US$83 return
Apr
US$121 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.