We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chicago Holiday Packages

Another View!
Chicago
sky deck
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 242,211 reviews and posted 50,978 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 were treated like royalty from the moment we arrived at the property. The entire staff went out of their way to make our stay pleasant and fun. We would definitely return and...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
This hotel is just like having your own pied a terre in a different city. It is clean, inviting and has an incredible roof deck. Close enough to the city that it's convenient, but...
1. Find your perfect hotel
2. Find the right flight
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...
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*
Jul
USD 157 return
Aug
USD 157 return
Sep
USD 157 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.