Winthrop Harbor Vacation Packages
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Top Winthrop Harbor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,494, price is now CA $986 per person
CA $986
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Terrible attitude of the front desk clerk.
Room smelled bad, dirty carpet.
Reviewed on Jun 24, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,655, price is now CA $1,719 per person
CA $1,719
per person
Sep 16 - Sep 21
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,869, price is now CA $1,295 per person
CA $1,295
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (493 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Winthrop Harbor Hotel Deals
LA VILLA MOTEL
1401 Sheridan Rd Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
The price is CA $75 per night from Jul 9 to Jul 10
CA $75
CA $87 total
Jul 9 - Jul 10
includes taxes & fees
6.8/10 (72 reviews)
"Needed a last minute place to stay, and this was clean and quiet, with attentive staff, though poorly maintained (eg old furniture stored in the hallway, bathroom exhaust did not work). The room had a huge hot tub in the corner with a wall mirror. Fantastic location, easy drive to downtown Zion and ..."
Reviewed on Jun 20, 2026
Motel Sun Inn
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from Jun 25 to Jun 26
CA $93
CA $108 total
Jun 25 - Jun 26
includes taxes & fees
6.8/10 (279 reviews)
"Staff was extremely pleasant and helpful. Motel is a bit dated and doesn't have the best lighting but appears its under new ownership thst are trying to update and modernize the building.. Not many amenities but location. Is good and the area is a quiet and close enough to travel."
Reviewed on Jun 16, 2026
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
The price is CA $254 per night from Jul 6 to Jul 7
CA $254
CA $290 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"This was our first time at a great Wolf Lodge. We like that it was close to other parks and a big mall. The swimming area was a lot of fun for our kids. The staff was kind and helpful. The prices in the restaurants were over the top for what the food was. Cleanliness was OK but the room was showing ..."
Reviewed on Jun 24, 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.
