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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 211,563 reviews and posted 51,627 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
“So special” 09/28/2016
From the moment when we arrived, until when we left, the staff was warm, welcoming, and so helpful. Room was great, and everything we needed. This is so close to everything and...
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2. Find the right flight
Build your luxury package
The Langham, Chicago
The Langham, Chicago
The people at the front door, at the club level check-in can not be nicer. I have never been to this hotel, but it will not be my last! The room is very well appointed with a...
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2. Find the right flight
Build your budget package
University Club of Chicago
University Club of Chicago
This gathering place of Chicago deal makers has comfortable beds, spacious rooms, a wonderful old school oak-walled library overlooking Millennium Park and the lakefront. Major...
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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*
Oct
$78 round trip
Nov
$81 round trip
Dec
$81 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.