Westchester Vacations from ￥176,152
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- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
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The Latest Westchester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sofitel Chicago Magnificent Mile
Downtown Chicago
Price was ￥218,096, price is now ￥176,152 per person
￥176,152
per person
Feb 20 - Feb 25
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,210 reviews)
Lovely hotel! Exceptionally clean and affordable!
Reviewed on Dec 14, 2025
Chicago luxury home suites
Downtown Chicago
Save 100% on your flight
Price was ￥564,895, price is now ￥393,365 per person
￥393,365
per person
Feb 20 - Feb 25
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.
Reviewed on Nov 26, 2025
La Banque Hotel
Price was ￥243,452, price is now ￥191,074 per person
￥191,074
per person
Feb 20 - Feb 25
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.
Reviewed on Nov 30, 2025
Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Price was ￥277,445, price is now ￥222,152 per person
￥222,152
per person
Feb 20 - Feb 25
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (137 reviews)
My wife and I really enjoyed our stay at this location. The accommodations were very nice. However, what really stuck out was the hotel staff, its the best that we have experienced.
Reviewed on Sep 5, 2025
Find the Best Westchester Vacation Packages
Westchester Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥12,649 per night from Jan 5 to Jan 6
￥12,649
￥14,847 total
Jan 5 - Jan 6, 2026
includes taxes & fees
8.8/10 Excellent! (3,489 reviews)
👍
Reviewed on Dec 15, 2025
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥12,608 per night from Jan 4 to Jan 5
￥12,608
￥19,555 total
Jan 4 - Jan 5, 2026
includes taxes & fees
9.2/10 Wonderful! (2,109 reviews)
Awesome stay in an amazing room - lobby and bar/restaurant area were excellent as well. Location was perfect for our show at the CIBC Theatre nearby.
Reviewed on Dec 10, 2025
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥11,654 per night from Dec 28 to Dec 29
￥11,654
￥13,681 total
Dec 28 - Dec 29
includes taxes & fees
8.6/10 Excellent! (1,987 reviews)
Very clean and the staff was wonderful!
Reviewed on Dec 13, 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
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.
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Westchester
Wendella's 90-min Chicago River Architecture Tour
￥7,083
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,866
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
