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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 2,32,851 reviews and posted 50,327 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
The Talbot was a wonderful hotel. We booked a suite deal that allowed us to book a two room suite for a very affordable rate. The hotel was in the center of everything and the...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
I was pleasantly surprised by the amenities and the style in this full service hotel. They had everything that anyone could hope for including a garage with an opener! I booked...
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2. Find the right flight
Build your budget package
University Club of Chicago
University Club of Chicago
My wife and I stayed here one night last weekend while attending a wedding. The hotel is in a great location; just at the corner of Monroe and Michigan Avenue, a block or so from...
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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*
Apr
US$ 89 round trip
May
US$ 101 round trip
Jun
find price 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.