Westchester Vacations from ￥333,923
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The Latest Westchester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥417,041, price is now ￥333,923 per person
￥333,923
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,914 reviews)
Great breakfast and fresh
Central location
Reviewed on Apr 24, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥683,288, price is now ￥590,618 per person
￥590,618
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.
Reviewed on Apr 23, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥692,188, price is now ￥609,616 per person
￥609,616
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,663 reviews)
London house is exceptionally clean, well located, in comforting after a long day of visiting tourism sites and seeing the city
Reviewed on Apr 24, 2026
Swissotel - Chicago
Downtown Chicago
Price was ￥667,108, price is now ￥590,898 per person
￥590,898
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,266 reviews)
Really good spot and location. Staff was super helpful and nice.
Reviewed on Apr 22, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was ￥386,170, price is now ￥342,951 per person
￥342,951
per person
Jun 11 - Jun 15
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,882 reviews)
Clean rooms, small rooms, small elevators. Friendly and helpful staff.
Reviewed on Apr 21, 2026
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 ￥18,379 per night from Apr 26 to Apr 27
￥18,379
￥21,577 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,132 reviews)
wifi wouldn’t connect, when we called the front desk to ask (I had work I needed to do, and specifically checked before booking that the room included wifi) was met with attitude to “just connect” even though the wifi network wasn’t visible or available. also, you have no control over the temperature ...
Reviewed on Apr 24, 2026
River Hotel
75 East Wacker Drive Chicago IL
The price is ￥18,870 per night from May 25 to May 26
￥18,870
￥22,437 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,122 reviews)
Wonderful and helpful sstaff. Excellent location
Reviewed on Apr 24, 2026
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,764 per night from Apr 29 to Apr 30
￥13,764
￥21,032 total
Apr 29 - Apr 30
includes taxes & fees
8.2/10 Very Good! (2,635 reviews)
The staff were extremely impressed and helpful. Help me with restaurant choices, where to go for tours. Only thing I regretted was not packing the proper clothes for the chance of weather. It was my personal birthday present to me and I did enjoyed myself.
Reviewed on Apr 24, 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.
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.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Westchester
Skydeck - Willis Tower Admission
￥7,012
per adult
96% of travellers recommend
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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.
