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
Фасолина
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 2,69,100 reviews and posted 52,947 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
This is a small boutique hotel at Delaware and Rush. It’s close to shopping and a number of great restaurants. We were there off season and got an amazing rate. In the summer...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
Our family stayed in one of the 3 bedroom apartments. We were looking for someplace convenient and with enough sleeping space. For the slightly higher cost than a traditional...
1. Find your perfect hotel
2. Find the right flight
Build your budget package
Carlton Inn Midway
Carlton Inn Midway
Cartlton Inn Midway was a great value for an overnight stay and 1 week park and fly. The staff was joyous and so accommodating. The shuttle took us to the restaurant of our...
1. Find your perfect hotel
2. Find the right flight
Cheap Flights to Chicago
Mar
find price round trip
Apr
find price round trip
May
find price 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.