Westchester Vacations from ￥109,316
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The Latest Westchester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥132,392, price is now ￥109,316 per person
￥109,316
per person
Jul 11 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (2,176 reviews)
Clean room, overall nice hotel, restaurant was nice for happy hour. Lobby smelled like an old lady and peltons in gym were broken. Overall lovely stay.
Reviewed on Jun 9, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥563,224, price is now ￥484,364 per person
￥484,364
per person
Aug 10 - Aug 14
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥393,374, price is now ￥343,296 per person
￥343,296
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,376 reviews)
We had requested for a 2pm checking but they gave us the room at 4pm and the normal checkin time is 3pm. Also the next day they did nit clean the room and we had requested that the beds and bathroom needs to be cleaned. They cleaned the room but left. Soaking wet towel on the bed. Little disappointed with our stay.
Reviewed on Jun 7, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ￥431,842, price is now ￥382,505 per person
￥382,505
per person
Aug 12 - Aug 16
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Nice staff clean room would stay again.
Reviewed on Jun 6, 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 ￥21,810 per night from Jun 29 to Jun 30
￥21,810
￥25,929 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,237 reviews)
"First, this is a historic hotel, and visitors should be aware that the rooms reflect the historic vibe. If you want modern, you need to stay down the street at the Hilton. The rooms were very cute and clean, and the tiling in the bathroom was beautiful. The hotel has a prime location with easy walking ..."
Reviewed on Jun 10, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
The price is ￥25,608 per night from Jul 1 to Jul 2
￥25,608
￥30,446 total
Jul 1 - Jul 2
includes taxes & fees
7.8/10 Good! (1,552 reviews)
"Enjoyed our stay"
Reviewed on Jun 10, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥25,505 per night from Jun 28 to Jun 29
￥25,505
￥29,070 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,645 reviews)
"The door to the restroom kept getting jammed and wouldn’t close properly. Our room also had no WiFi… the staff couldn’t figure out why it wasn’t working."
Reviewed on Jun 10, 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
4.5/5(2,149 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(461 reviews)
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
4.5/5(4,925 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
￥6,354
per adult
94% 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.
