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 229,610 reviews and posted 51,217 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
Really great hotel. Absolutely fantastic. In the centre of Chicago - not far away from shopping malls and great restaurants. Concierge was amazing. Was looking for various...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Guesthouse Hotel
The Guesthouse Hotel
Our second visit - equally as enjoyable as the first! Enjoyed the accommodations, great staff and proximity to the local neighborhood. Andersonville is just up the street and...
1. Find your perfect hotel
2. Find the right flight
Build your budget package
Carlton Inn Midway
Carlton Inn Midway
We stayed at the Carlton Inn Midway as a Park and Fly stay. The room was newly remodeled and very clean. We stayed one night, enjoyed the included breakfast and they shuttled us...
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*
Mar
US$79 round trip
Apr
US$89 round trip
May
US$101 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.