
Westchester Holidays from £869
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- Better togetherSave up to £750 when you book a flight and hotel together*
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- Rest easyPackages with flights are ATOL protected
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

Hotel Felix River North/Magnificent Mile
Reviewed on 18 Jun 2026

Level Chicago Fulton Market
Reviewed on 18 Jun 2026

Great Wolf Lodge Illinois
Reviewed on 18 Jun 2026

Kinzie Hotel
Reviewed on 18 Jun 2026

The Emily Hotel
Reviewed on 19 Jun 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

Congress Plaza Hotel
"The facilities are very old, and there is a musty smell in the room."
Reviewed on 18 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
"seems like we are visiting every other month to meet up with friends. We have already recommended this hotel many times and will definitely be staying again."
Reviewed on 19 Jun 2026

Hyatt Regency O'Hare Chicago
"Great staff and amenities"
Reviewed on 19 Jun 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.

Michigan Avenue
You can find the perfect gifts to bring home 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
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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.












