Winthrop Harbor Vacations from ￥290,255
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Winthrop Harbor Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥367,903, price is now ￥290,255 per person
￥290,255
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Great place to stay the young lady checking us in was not very friendly. Never received my complimentary drinks. There was never anyone at the bar. Valet guy was very helpful!!! Other than the small things it was a good stay!!!
Reviewed on Mar 29, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥426,090, price is now ￥293,447 per person
￥293,447
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great breakfast for the price. A true gem for downtown Chicago. The only bad thing I experienced was the gentleman standing outside side the front doors smoking pot every night. He was a person staying at the RIU. I was there to see a Dr at Northwestern for my rare heart and lung condition and that smell was not good for my heart or lungs
Reviewed on Mar 30, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥458,800, price is now ￥362,534 per person
￥362,534
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Thank you for your exceptional hospitality
Reviewed on Mar 29, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥369,722, price is now ￥300,613 per person
￥300,613
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The hotel offered many amenities including gym, sauna, dining on the ground level and effective housekeeping. The hotel was walking distance to many nearby restaurants and activities.
Reviewed on Mar 30, 2026
Find the Best Winthrop Harbor Vacation Packages
Winthrop Harbor Hotel Deals
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
Fully refundableReserve now, pay when you stay
The price is ￥19,109 per night from Apr 14 to Apr 15
￥19,109
￥21,780 total
Apr 14 - Apr 15
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
I would never stay here again. Rooms are old inside and need a remodel. The staff is ok, but very slow. This water park had too many people and not very enjoyable. I don’t agree with people in the surrounding area to be able buy a one day pass to visit the park. It was just awful and some of the ...
Reviewed on Mar 30, 2026
Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is ￥14,338 per night from Apr 13 to Apr 14
￥14,338
￥17,076 total
Apr 13 - Apr 14
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
Super breakfast and convenient location at a decent ratr.
Reviewed on Mar 26, 2026
Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant
13340 Hospitality Ct Mount Pleasant WI
Fully refundableReserve now, pay when you stay
The price is ￥9,811 per night from Apr 5 to Apr 6
￥9,811
￥11,137 total
Apr 5 - Apr 6
includes taxes & fees
8.2/10 Very Good! (500 reviews)
Was so much cleaner and not run down like many in the area. All 5 of us felt safe and comfortable. Our room was huge and was the biggest room we ever stayed in! We'll be in Milwaukee a lot this summer for work and this will be our gomto Clean, no funky smell, everything worked, staff was all pleasent. ...
Reviewed on Mar 29, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
