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 Vacation Packages

Photo provided by ©4Corners
Another View!
sky deck
Chicago Vacation Packages
Want to book a vacation to Chicago? Whether you're off for a romantic vacation, family trip, or an all-inclusive holiday, Chicago vacation packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect vacation package for Chicago on TripAdvisor by comparing Chicago hotel and flight prices. Travelers like you have written 133,211 reviews and posted 26,690 candid photos for Chicago hotels. Book your Chicago vacation today!
Or build your own Chicago vacation package
Build your family-friendly package
Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
“Fantastic” 01/29/2015
Great Hotel, excellent service, excellent food, they didn't press my Girlfriend Dress up to he specifications but no one's ironing skills are good enough for her. The light...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Langham, Chicago
The Langham, Chicago
We recently stayed at the Langham to celebrate a special birthday.. From the moment we walked through the door we knew we had made the right choice! The hotel excels in every way...
1. Find your perfect hotel
2. Find the right flight
Build your budget package
University Club of Chicago
University Club of Chicago
“Good value” 12/18/2014
Excellent location in downtown Chicago just a half block from Millennium Park and a block from the Art museum. Hotel is dated but room was refurbished and very comfortable. Gym...
1. Find your perfect hotel
2. Find the right flight
Cheap Flights to Chicago
All Washington to Chicago (WAS-CHI) fares found by travelers in the past 72 hours*
Feb
$93 round trip
Mar
$93 round trip
Apr
$93 round trip
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers 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.