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Chicago Holiday Packages

Another View!
Cloud Gate, Grant Pk Chicago.. awesome
Wrigley sign
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 241,779 reviews and posted 50,713 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
We enjoy staying here when we come back to Chicago. Friendly staff , clean rooms and helpful staff Great location. Enjoyed the coffee each morning in the lobby. Appreciated the...
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The Guesthouse Hotel
The Guesthouse Hotel
This hotel is just like having your own pied a terre in a different city. It is clean, inviting and has an incredible roof deck. Close enough to the city that it's convenient, but...
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University Club of Chicago
University Club of Chicago
Did stay here but went for dinner in the restaurant. Everything was good! The lobster chowder was great and the steak as well! Heard that they have different menu over the year so...
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Cheap Flights to Chicago
All Washington to Chicago (WAS-CHI) fares found by travellers in the past 72 hours*
Jul
US$157 round trip
Aug
US$157 round trip
Sep
US$157 round trip
†  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.