Westchester Holidays from £1,367
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Your Westchester Holiday
A great way to experience this lively city is with a tailor-made Westchester holiday package. Stay in the neighbourhood 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 Centre Mall and Frank Lloyd Wright Historic District. Don't put off your visit to this city any longer. The perfect Westchester holiday is only a few clicks away with Expedia.
Top Westchester Flight + Hotel Deals
Level Chicago Fulton Market
Reviewed on 25 Apr 2026
Swissotel - Chicago
Reviewed on 27 Apr 2026
Fairmont Chicago at Millennium Park
Reviewed on 24 Apr 2026
LondonHouse Chicago, Curio Collection by Hilton
Reviewed on 28 Apr 2026
Westchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 16,700 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Brookfield Zoo, Rosemont Theatre and Parkway Bank Park Entertainment District |
Top hotels in Westchester
Hotel Felix River North/Magnificent Mile
Great location nice hotel!
Reviewed on 28 Apr 2026
River Hotel
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it
Reviewed on 29 Apr 2026
Club Quarters Hotel, Central Loop, Chicago
Great check in and check out experience
Reviewed on 29 Apr 2026
Popular places to visit
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.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
What to do in Westchester
Skydeck - Willis Tower Admission
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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. Flight-inclusive packages are ATOL protected.
