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Chicago Holiday Packages

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Chicago
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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 250,451 reviews and posted 50,990 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
“Awesome stay!” 18/08/2017
Fast and convenient check in. Very courteous staff. The room was very clean and comfortable. The flat screen tv allowed us to mirror my cell phone to it and I was able to...
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2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
I love this hotel!!!!!!!! My husband, friends, and their children arrived as last-minute refugees from a disastrous Airbnb fail, and the minute we walked into the lobby and were...
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2. Find the right flight
Build your budget package
University Club of Chicago
University Club of Chicago
“Awesome.” 11/08/2017
We have staying at the University Club of Chicago. The food and rooms are awesome. The gallery on the 12th is a great place to be on Wednesday nights during the fireworks. The...
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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*
Sep
US$89 round trip
Oct
US$89 round trip
Nov
US$89 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.