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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 229,215 reviews and posted 51,129 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
Really great hotel. Absolutely fantastic. In the centre of Chicago - not far away from shopping malls and great restaurants. Concierge was amazing. Was looking for various...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
I would 100% recommend The Guesthouse for anyone looking for an extended stay or even for a couple of nights. Gorgeous hotel, friendly staff and DOG FRIENDLY! My wife and I...
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2. Find the right flight
Build your budget package
Carlton Inn Midway
Carlton Inn Midway
Living in central Wisconsin but flying at 7:05 am from Chicago Midway meant looking for a park/sleep/fly option. Fortunately we found the Carlton Inn Midway. First impressions...
1. Find your perfect hotel
2. Find the right flight
Cheap Flights to Chicago
All Washington to Chicago (WAS-CHI) fares found by travellers in the past 72 hours*
Mar
US$79 return
Apr
US$89 return
May
US$101 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.