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Chicago Vacation Packages

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Chicago Vacation Packages
Want to book a vacation to Chicago? Whether you're off for a romantic vacation, family trip, or an all-inclusive holiday, Chicago vacation packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect vacation package for Chicago on TripAdvisor by comparing Chicago hotel and flight prices. Travelers like you have written 140,833 reviews and posted 28,810 candid photos for Chicago hotels. Book your Chicago vacation today!
Or build your own Chicago vacation package
Build your family-friendly package
The Talbott Hotel
The Talbott Hotel
“OUTSTANDING!” 04/25/2015
I'm so glad I read through the reviews on Tripadvisor and selected The Talbott Hotel. We enjoyed a wonderful stay at this charming boutique hotel. Location is superb and the...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Langham, Chicago
The Langham, Chicago
We stayed for 8 nights and got an amazing deal with a Linger at the Langham rate. I am not going to add to all the superlatives that have already been used by other travellers...
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2. Find the right flight
Build your budget package
University Club of Chicago
University Club of Chicago
Best location for seeing Chicago, just across from Millenial Park and close to Art Institute. Lovely rooms and fantastic views from the dining room. Valet parking. Just a...
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2. Find the right flight
Cheap Flights to Chicago
All Washington to Chicago (WAS-CHI) fares found by travelers in the past 72 hours*
May
$145 round trip
Jun
$145 round trip
Jul
$145 round trip
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers 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.