Westchester Holidays
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Top Flight + Hotel Deals in Westchester
Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Chicago - Willowbrook
Price was €339, price is now €282 per person
€282
per person
1 May - 4 May
found 11 hours ago
Return flight included
Orlando (MCO) to Chicago (ORD)
6.4/10 (1,004 reviews)
Check in was quick and simple. The room was clean and that's all i needed for a few hours until i went to the airport. The extra lock on the,door was broken. There also was a coffee pot, but no coffee in the room
Reviewed on 8 Feb 2026
Holiday Inn Express Rolling Meadows - Schaumburg Area by IHG
Price was €402, price is now €336 per person
€336
per person
1 May - 4 May
found 12 hours ago
Return flight included
Orlando (MCO) to Chicago (ORD)
8.2/10 Very Good! (687 reviews)
Was super clean rooms,sheets and everything else.The staff was very nice .
Reviewed on 25 Nov 2025
Courtyard by Marriott Chicago Midway Airport
Bedford Park
Price was €475, price is now €399 per person
€399
per person
1 May - 4 May
found 11 hours ago
Return flight included
Orlando (MCO) to Chicago (ORD)
8.2/10 Very Good! (1,001 reviews)
It was better than we thought it would be! They had really nice rooms for reasonable price. Clean and neat. Staff was friendly and easy check In/check out process!
Reviewed on 15 Feb 2026
Top hotels in Westchester
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €188 per night from 13 Mar to 14 Mar
€188
13 Mar - 14 Mar
includes taxes & fees
8/10 Very Good! (9,906 reviews)
The room and hotel is a bit run down as most places over a century old
Reviewed on 18 Feb 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €122 per night from 4 Mar to 5 Mar
€122
4 Mar - 5 Mar
includes taxes & fees
9.2/10 Wonderful! (3,361 reviews)
Breakfast was nice
Reviewed on 17 Feb 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is €162 per night from 5 Mar to 6 Mar
€162
5 Mar - 6 Mar
includes taxes & fees
8.4/10 Very Good! (2,617 reviews)
It was great
Reviewed on 12 Feb 2026
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.
Popular places to visit
Wrigley Field
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(14 reviews)
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.
Navy Pier
4/5(125 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Westchester
Chicago: Navy Pier Centennial Wheel Ticket
€20
per adult
88% of travellers recommend
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