Westchester Vacations from AED6,334
Book a Hotel + Flight together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to AED 148 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Westchester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
Jul 13 - Jul 16
found 13 hours ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Trump International did a great job and is my favorite hotel in Chicago to stay at!
Reviewed on 21 May 2025
Find the Best Westchester Vacation Packages
Westchester Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 438 per night from May 26 to May 27
AED 438
AED 514 total
includes taxes & fees
26 May - 27 May
7.8/10 Good! (8,899 reviews)
"The hotel needs renovation"
Reviewed on 22 May 2025
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 485 per night from May 25 to May 26
AED 485
AED 661 total
includes taxes & fees
25 May - 26 May
8/10 Very Good! (2,853 reviews)
"Stay was nice"
Reviewed on 20 May 2025
Ambassador Hotel Chicago
1301 N State Pkwy, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 112 per night from May 26 to May 27
AED 112
AED 609 total
includes taxes & fees
26 May - 27 May
8.4/10 Very Good! (1,003 reviews)
"We reserved a double room for one night to go to a concert at Soldier Field. We booked a month out but most options (aside from this) were taken. Room was very clean, comfortable and quiet. The view from our windows were also nice, but private. Only caveat to staying here is the required resort fee ..."
Reviewed on 21 May 2025
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.
Discover the most popular places to visit in Westchester
Wrigley Field
4.5/5(2,128 reviews)
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
Six Flags Great America
4.5/5(347 reviews)
Enjoy the excitement at Six Flags Great America and see why people love this theme park in Gurnee. Stroll along the lakeside or visit the shops in this family-friendly area.
Michigan Avenue
4.5/5(332 reviews)
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.