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.
WINNER WONDERLAND
Win Big When You Book on TripAdvisor

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 220,634 reviews and posted 50,002 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 an extended weekend here in October, 2016. From the bellhops to reception desk, from the concierge to the housekeepers, the staff were incredibly nice, efficient, helpful...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
I made a last minute decision to get a hotel room. I did not want to stay downtown as I usually do. I called them up and they had a few rooms left and had a special that was...
1. Find your perfect hotel
2. Find the right flight
Build your budget package
Carlton Inn Midway
Carlton Inn Midway
Smooth check in. Requested 2nd floor room not knowing there was no elevator. But managed. Clean room. Comfortable bed. Nice continental breakfast. The airport drivers to and back...
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*
Dec
US$81 return
Jan
US$97 return
Feb
US$81 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.