Winthrop Harbor Vacation Packages
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Top Winthrop Harbor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was CA $1,324, price is now CA $846 per person
CA $846
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
It was a nice room. Only complaint would be air conditioning. I don’t do hot. Hate sweating. Had turned to 65 and still not really cold. Otherwise overall nice.
Reviewed on May 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,469, price is now CA $929 per person
CA $929
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,214, price is now CA $1,432 per person
CA $1,432
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Clean and have a beautiful view of the lake
Reviewed on May 26, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,287, price is now CA $1,486 per person
CA $1,486
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.
Reviewed on May 18, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,410, price is now CA $952 per person
CA $952
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,711 reviews)
Breakfast wasn’t anything spectacular, alcohol and coffee bar felt lacking but nice to have. Excellent location with tons of bars, restaurants and cafes around.
Reviewed on May 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 $226 per night from Jun 3 to Jun 4
CA $226
CA $258 total
Jun 3 - Jun 4
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"The people who were working here OUTSTANDINGLY KIND, and EXCELLENT at their jobs. They honestly cared about making our stay here work out ."
Reviewed on May 27, 2026
Hotel Indigo Chicago-Vernon Hills by IHG
450 N Milwaukee Ave Vernon Hills IL
Fully refundable
The price is CA $155 per night from Jun 9 to Jun 10
CA $155
CA $172 total
Jun 9 - Jun 10
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
"The beds are a little hard and water could be hotter for the shower but other than that it’s a good place to stay."
Reviewed on May 25, 2026
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Jun 28 to Jun 29
CA $157
CA $175 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Todo"
Reviewed on May 25, 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.
