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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Staybridge Suites, Lincolnshire by IHG
The Langham, Chicago
The Peninsula Chicago

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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 $151 per night from Apr 16 to Apr 17
CA $151
CA $177 total
Apr 16 - Apr 17
includes taxes & fees
8/10 Very Good! (10,037 reviews)
Property is always well maintained, very clean and tidy

Reviewed on Apr 6, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Apr 12 to Apr 13
CA $191
CA $224 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (4,063 reviews)
Amazing hotel, felt like a star in my suite! Accessible location and wonderful welcoming staff made this some place I wish we had stayed more than one night.

Reviewed on Apr 5, 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Apr 27 to Apr 28
CA $205
CA $240 total
Apr 27 - Apr 28
includes taxes & fees
8.6/10 Excellent! (5,824 reviews)
The room was very clean but the amenities are quite dirty. In general is a big hotel with a lot of movement, many families and a lot of people everywhere, so the breakfast (which is great by the way) is very busy.

Reviewed on Apr 6, 2026

Embassy Suites by Hilton Chicago Downtown River North
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.