
Winthrop Harbor Holidays
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Top Flight + Hotel Deals in Winthrop Harbor
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,918, price is now €1,155 per person
€1,155
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025

The Emily Hotel
Downtown Chicago
Price was €1,420, price is now €868 per person
€868
per person
2 Nov - 7 Nov
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug 2025

Park Hyatt Chicago
Downtown Chicago
Price was €1,979, price is now €1,240 per person
€1,240
per person
2 Nov - 7 Nov
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was €1,825, price is now €1,216 per person
€1,216
per person
10 Oct - 14 Oct
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Amazing service and friendly staff! Great place and within walkable distances to near by shops.
Reviewed on 23 Aug 2025
Top hotels in Winthrop Harbor

Motel Sun Inn
301 Sheridan Road, Winthrop Harbor, IL
Fully refundableReserve now, pay when you stay
The price is €59 per night from 25 Aug to 26 Aug
€59
25 Aug - 26 Aug
includes taxes & fees
6.6/10 (253 reviews)
"Pleasantly surprised."
Reviewed on 17 Aug 2025

LA VILLA MOTEL
1401 Sheridan Rd, Winthrop Harbor, IL
Fully refundable
The price is €61 per night from 1 Sept to 2 Sept
€61
1 Sept - 2 Sept
includes taxes & fees
6.4/10 (45 reviews)
"Good"
Reviewed on 13 Aug 2025

DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83, Mundelein, IL
Fully refundableReserve now, pay when you stay
The price is €104 per night from 1 Sept to 2 Sept
€104
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
Great place to stay
"The staff was amazing, very helpful and friendly. The room was very comfortable, but needed some repair (Wallpaper peeling in multiple area's). The pool area is very spacious. The lobby is nice and accommodating with no rooms at that end so noise was not an issue."
Reviewed on 23 Aug 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.