Westchester Vacation Packages

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Your Westchester Vacation

A great way to experience this lively city is with a tailor-made Westchester vacation package. Stay in the neighborhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our package deals are all about you. A trip to Westchester is a great opportunity to sightsee. Be sure to visit renowned attractions like Brookfield Zoo, Oakbrook Center Mall and Frank Lloyd Wright Historic District. Don't put off your visit to this city any longer. The perfect Westchester vacation is only a few clicks away with Expedia.

Top Westchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Waldorf Astoria Chicago
DoubleTree by Hilton Chicago - Alsip
Aloft Chicago Downtown River North
Hyatt Regency Chicago

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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Westchester Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Feb 24 to Feb 25
CA $121
CA $142 total
Feb 24 - Feb 25
includes taxes & fees
8/10 Very Good! (9,863 reviews)
Good location for many activities. Room was good but less than great.

Reviewed on Feb 7, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Mar 4 to Mar 5
CA $162
CA $228 total
Mar 4 - Mar 5
includes taxes & fees
9.2/10 Wonderful! (3,323 reviews)
Friendly staff, tasteful room

Reviewed on Feb 11, 2026

Hotel Riu Plaza Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $267 per night from Mar 7 to Mar 8
CA $267
CA $313 total
Mar 7 - Mar 8
includes taxes & fees
8.2/10 Very Good! (2,215 reviews)
A very good value. A bit worn, great bed but half the price of the Westin Denver airport.

Reviewed on Feb 8, 2026

Hilton Chicago O'Hare Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.