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Chicago Vacation Packages

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Chicago Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG
The Wade
Pendry Chicago
Harrah's Joliet Casino & Hotel
Level Chicago – Old Town
The Langham, Chicago
theWit Chicago, a Hilton Hotel
InterContinental Chicago Magnificent Mile by IHG

Chicago Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
InterContinental Chicago Magnificent Mile by IHG
Park Hyatt Chicago
LondonHouse Chicago, Curio Collection by Hilton

Chicago Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Wade
Virgin Hotels Chicago
Trump International Hotel & Tower Chicago
Pendry Chicago

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Spirit Airlines
JetBlue Airways
Delta