
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

Hilton Chicago
Reviewed on Jul. 16, 2025

Virgin Hotels Chicago
Reviewed on Jul. 15, 2025


Westchester Hotel Deals

Congress Plaza Hotel
Reviewed on Jul. 15, 2025

InterContinental Chicago Magnificent Mile by IHG
Reviewed on Jul. 16, 2025

Hilton Chicago/Magnificent Mile Suites
Reviewed on Jul. 14, 2025
Discover the most popular places to visit in Westchester

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
What to do in Westchester

Wendella's 90-min Chicago River Architecture Tour

Chicago By Night River & Lake Cruise
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