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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 231,967 reviews and posted 51,952 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
Shelter - a word sometimes used carelessly, without thought or consideration of its basic and true meaning. Where would we be without it? Do yourself a favor: stay at The...
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2. Find the right flight
Build your budget package
Carlton Inn Midway
Carlton Inn Midway
Stayed the night before an early morning flight to California on 3/10. Pretty much got to the room & went to bed as we had to be up at 3:00 am. Room was clean, bed was comfy...
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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 return
May
US$101 return
Jun
find price return
†  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.