Winslow Vacations from ￥297,716
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- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
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The Latest Winslow Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥547,828, price is now ￥474,038 per person
￥474,038
per person
Apr 4 - Apr 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was amazing. Staff was fantastic. Best Hotel we have ever stayed at
Reviewed on Feb 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥354,054, price is now ￥307,436 per person
￥307,436
per person
Apr 4 - Apr 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (413 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥338,152, price is now ￥301,452 per person
￥301,452
per person
Apr 18 - Apr 21
found 4 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet
Reviewed on Feb 22, 2026
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was ￥356,949, price is now ￥319,891 per person
￥319,891
per person
Apr 18 - Apr 21
found 4 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
8.8/10 Excellent! (1,870 reviews)
Such a convenient location, staff were very friendly and efficient
Reviewed on Mar 1, 2026
Find the Best Winslow Vacation Packages
Winslow Hotel Deals
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is ￥16,315 per night from Mar 22 to Mar 23
￥16,315
￥18,105 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (867 reviews)
Clean rooms, comfortable bed, good breakfast on the morning. Great location with plenty of dining options close by.
Reviewed on Mar 2, 2026
Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
The price is ￥12,299 per night from Mar 22 to Mar 23
￥12,299
￥13,467 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (834 reviews)
Clean room, nice staff
Reviewed on Feb 28, 2026
Country Inn & Suites by Radisson, Stockton, IL
200 Dillon Ave Stockton IL
The price is ￥13,368 per night from Mar 23 to Mar 24
￥13,368
￥14,835 total
Mar 23 - Mar 24
includes taxes & fees
8.4/10 Very Good! (652 reviews)
Clean room, nice staff.
Reviewed on Feb 20, 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.
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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.
