
Winthrop Harbor Vacations from $231
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The Latest Winthrop Harbor vacation packages
Price found within the past 48 hours. Click for updated prices.

Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Save 100% on your flight
Price was $428, price is now $231 per person
$231
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
19.2/10 Exceptional! (325 reviews)
Clean nice place to stay
Reviewed on Nov 19, 2025

Level Chicago – Old Town
Downtown Chicago
Price was $3,257, price is now $1,529 per person
$1,529
per person
Dec 28 - Jan 3
found 17 hours ago
Roundtrip flight included
Dallas (DFW) 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


The Westin Michigan Avenue Chicago
Downtown Chicago
Save 100% on your flight
Price was $970, price is now $486 per person
$486
per person
Dec 20 - Dec 23
found 4 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.
Reviewed on Nov 17, 2025

Holiday Inn Chicago - Schaumburg by IHG
Save 100% on your flight
Price was $447, price is now $237 per person
$237
per person
Dec 26 - Dec 31
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
16.4/10 Exceptional! (999 reviews)
Rooms were clean and overall the hotel was nice
Reviewed on Nov 1, 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 25 to Nov 26
$71 total
Nov 25 - Nov 26
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 20 to Nov 21
$67 total
Nov 20 - Nov 21
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
$65 nightly
The price is $72 total per night from Dec 8 to Dec 9
$72 total
Dec 8 - Dec 9
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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