Winthrop Harbor Vacation Packages
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Top Winthrop Harbor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,359, price is now CA $878 per person
CA $878
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.
Reviewed on Apr 24, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,467, price is now CA $1,649 per person
CA $1,649
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Absolutely fantastic will be back
Reviewed on Apr 27, 2026
Winthrop Harbor Hotel Deals
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from May 7 to May 8
CA $162
CA $185 total
May 7 - May 8
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
This was a great time for our daughter’s brithday
Reviewed on May 1, 2026
Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from May 4 to May 5
CA $141
CA $167 total
May 4 - May 5
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
Good for the price. Near to RecPlex. Complimentary beer per adult
Reviewed on May 1, 2026
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from May 17 to May 18
CA $143
CA $158 total
May 17 - May 18
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
The hotel itself is clean, but for the price of a room I do think breakfast should be included.
Reviewed on Apr 20, 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.
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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.
