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.
Want the lowest hotel prices? You're in the right place. We check 200+ sites for you.

Chicago Holiday Packages

Photo provided by ©4Corners
Another View!
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 225,678 reviews and posted 50,441 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
Upon check in we were noticed we were going to be the last guests before the hotel was due to be closed for renovation. The staff and accommodations were very comfortable and...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
This is a fabulous property. The room was outstanding, the employees bright and friendly, and the location was great. The price was good for a Chicago hotel and the optional...
1. Find your perfect hotel
2. Find the right flight
Build your budget package
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
We rented two rooms for my family because we got a great rate (yeah, it's January). Here are the pluses and minuses: Pluses: Great location - one block of Michigan Ave near...
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*
Feb
US$77 round trip
Mar
US$89 round trip
Apr
US$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 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.