
Winthrop Harbor Vacations from ¥200,594
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The Latest Winthrop Harbor Vacation Packages
Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥256,630, price is now ¥200,594 per person
¥200,594
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
There aren’t many options but there is health ones with fresh vegetables and fruits.
Reviewed on Dec 29, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥385,898, price is now ¥274,520 per person
¥274,520
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Absolutely loved the hotel.Grand Dulxe Suite was huge with amazing views.All staff top notch.
Reviewed on Dec 27, 2025

The Peninsula Chicago
Downtown Chicago
Price was ¥399,685, price is now ¥297,235 per person
¥297,235
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Everything was just fine. However, this property does not have a lobby bar or convenient place to meet and have a drink. There is Z Bar, which appears to maybe be leased by the property to an outside group? Either way, it was not convneient. There were never seats available at the bar itself, and a 45 minurte minimim wait for one of the few tables. The patrons appeared to maybe be 50% hotel huests and 50% other.
Reviewed on Dec 29, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ¥285,935, price is now ¥221,613 per person
¥221,613
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥260,674, price is now ¥203,887 per person
¥203,887
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Rooms were clean, staff was super friendly. Kind of wish there was a spa or gym but free breakfast was a nice touch. You cant beat the location.
Reviewed on Dec 28, 2025
Find the Best Winthrop Harbor Vacation Packages
Winthrop Harbor Hotel Deals

LA VILLA MOTEL
1401 Sheridan Rd Winthrop Harbor IL
Fully refundable
The price is ¥9,599 per night from Jan 5 to Jan 6
¥9,599
¥11,134 total
Jan 5 - Jan 6, 2026
includes taxes & fees
6.6/10 (68 reviews)
Good service
Reviewed on Sep 30, 2025

La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
Fully refundableReserve now, pay when you stay
The price is ¥9,449 per night from Jan 1 to Jan 2
¥9,449
¥10,581 total
Jan 1 - Jan 2, 2026
includes taxes & fees
7.8/10 Good! (1,462 reviews)
Nice place clean very convenient hot breakfast
Reviewed on Dec 24, 2025

Wingate by Wyndham Gurnee
6090 Gurnee Mills Blvd E Gurnee IL
Fully refundableReserve now, pay when you stay
The price is ¥12,909 per night from Jan 4 to Jan 5
¥12,909
¥14,456 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Friendly staff
Reviewed on Dec 23, 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.
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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.
