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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 238,180 reviews and posted 52,792 candid photos for Chicago hotels. Book your Chicago vacation today!
Or build your own Chicago vacation package
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The Talbott Hotel
The Talbott Hotel
Everyone was friendly and helpful. They informed me very early when my room was ready since we arrived very early. The room is small but that was expected. Bathrooms are very...
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Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
Guesthouse is the best of a Hotel and an apartment. We loved the spacious rooms, high ceilings, contemporary design details and full kitchen, washer/dryer. We saw a ball game at...
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Build your budget package
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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2. Find the right flight
Cheap Flights to Chicago
All Washington to Chicago (WAS-CHI) fares found by travelers in the past 72 hours*
Jun
$149 round trip
Jul
$149 round trip
Aug
$149 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.