Winthrop Harbor Vacations from $204
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The Latest Winthrop Harbor vacation packages
Price found within the past 48 hours. Click for updated prices.
The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,177, price is now $516 per person
$516
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
Great location and staff was very accommodating. Rooms were on the small side.
Reviewed on Nov 19, 2025
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Save 100% on your flight
Price was $736, price is now $431 per person
$431
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,003 reviews)
Great location and room for the price. Restaurant downstairs is also very nice if you wanted to grab a meal without leaving. Only a few hundred yards from Blue Line stop which goes right to the airport, and the welcome drink was a nice touch. Staff was also super friendly and accommodating.
Reviewed on Nov 10, 2025
Hyatt House Chicago West Loop
Downtown Chicago
Save 100% on your flight
Price was $455, price is now $273 per person
$273
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
17.6/10 Exceptional! (1,079 reviews)
We Truly Enjoyed our stay. staff was Great . Helpful and Pleasant.
Highly recommend staying here.
Reviewed on Nov 17, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,522, price is now $918 per person
$918
per person
Dec 28 - Jan 2
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025
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LA VILLA MOTEL
1401 Sheridan Rd Winthrop Harbor IL
Fully refundable
$61 nightly
The price is $71 total per night from Nov 26 to Nov 27
$71 total
Nov 26 - Nov 27
Total with taxes and fees
6.6/10 (67 reviews)
Good service
Reviewed on Sep 30, 2025
Motel Sun Inn
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
$58 nightly
The price is $67 total per night from Nov 23 to Nov 24
$67 total
Nov 23 - Nov 24
Total with taxes and fees
6.8/10 (275 reviews)
I have stayed here several times in the last year and a half. The room is very clean! Staff is very kind and helpful! Good rate! Thank you again for everything!
Reviewed on Nov 11, 2025
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $69 total per night from Nov 24 to Nov 25
$69 total
Nov 24 - Nov 25
Total with taxes and fees
7.8/10 Good! (1,404 reviews)
All good.
Reviewed on Nov 15, 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.
Find the Best Winthrop Harbor Vacation Packages
Winthrop Harbor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 6,800 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
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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.