Winthrop Harbor Vacations from ￥291,128
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The Latest Winthrop Harbor Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥351,120, price is now ￥291,128 per person
￥291,128
per person
Jan 17 - Jan 21
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
FOOD WAS GOOD, JUST A LITTLE COLD, BUT NO MAJOR PROBLEMS
Reviewed on Nov 12, 2025
Pendry Chicago
Downtown Chicago
Price was ￥478,928, price is now ￥418,007 per person
￥418,007
per person
Jan 2 - Jan 8
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.
Reviewed on Nov 12, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥466,364, price is now ￥410,922 per person
￥410,922
per person
Jan 2 - Jan 8
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥464,252, price is now ￥415,319 per person
￥415,319
per person
Jan 2 - Jan 8
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
The breakfast exceeded my expectations. I loved this hotel. Everything was great I will be staying again.
Reviewed on Nov 13, 2025
Arlo Chicago
Downtown Chicago
Price was ￥456,322, price is now ￥412,413 per person
￥412,413
per person
Jan 2 - Jan 8
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
We felt welcomed and supported in every way. Tasteful, artistic, comfortable, convenient, fun, good food. Terrific staff. Will definitely come again. Highly recommend.
Reviewed on Nov 12, 2025
Find the Best Winthrop Harbor Vacation Packages
Winthrop Harbor Hotel Deals
Motel Sun Inn
301 Sheridan Road, Winthrop Harbor, IL
Fully refundableReserve now, pay when you stay
The price is ￥8,735 per night from Nov 16 to Nov 17
￥8,735
￥10,132 total
Nov 16 - Nov 17
includes taxes & fees
6.8/10 (272 reviews)
Clean rooms. Friendly owners.
Reviewed on Oct 20, 2025
LA VILLA MOTEL
1401 Sheridan Rd, Winthrop Harbor, IL
Fully refundable
The price is ￥9,445 per night from Nov 24 to Nov 25
￥9,445
￥10,954 total
Nov 24 - Nov 25
includes taxes & fees
6.6/10 (65 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 ￥10,345 per night from Nov 17 to Nov 18
￥10,345
￥11,584 total
Nov 17 - Nov 18
includes taxes & fees
7.8/10 Good! (1,399 reviews)
Check in was great. The staff was kind and courteous.
Reviewed on Nov 8, 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.
