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Chicago Vacation Packages

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Chicago
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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 256,069 reviews and posted 50,141 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
We spent 4 nights at The Talbott in late September. Everything went smoothly from check-in to check-out. The entire hotel and restaurant staff were very friendly. Our room was...
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2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
My husband and I stayed at the Guesthouse Hotel while visiting our daughter who lives nearby. We were so impressed with the greeting we received from the staff. The lobby is...
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2. Find the right flight
Build your budget package
Carlton Inn Midway
Carlton Inn Midway
We parked at this hotel and went to the front desk to check in. The woman at the front desk checked us in quite quickly. When we got to our room, I noticed it was a small but...
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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*
Nov
US$203 round trip
Dec
US$97 round trip
Jan
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.