Winthrop Harbor Vacation Packages
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Top Winthrop Harbor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Naperville/Warrenville
Price was CA $1,084, price is now CA $757 per person
CA $757
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Minor issues: The room was fairly clean. There was some dust in the bathroom, furniture and candy found on the floor under the table from the previous guests. The room was cleaned during our stay, but they did not restock our toilet paper.
Reviewed on May 5, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,735, price is now CA $1,196 per person
CA $1,196
per person
Jul 22 - Jul 25
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
Viceroy Chicago
Downtown Chicago
Price was CA $2,215, price is now CA $1,542 per person
CA $1,542
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,231 reviews)
I don’t think I have ever encountered a more polite, charming, and informed staff. As someone who has worked in the service industry I assume that your training program does an excellent job. The hotel is beautiful and well maintained. We’ll be back.
Reviewed on May 25, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,855, price is now CA $1,294 per person
CA $1,294
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,017 reviews)
The room was nice, quick and easy check in. Will stay again when in chicago
Reviewed on May 26, 2026
JW Marriott Chicago
Downtown Chicago
Price was CA $1,345, price is now CA $950 per person
CA $950
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Good location close to many attractions like sears tower, the bean, river boat tours... nuce rooms ... public parking 1/2 block from premises .. just an overal great property with excellent convenience for tourists type activities
Reviewed on May 3, 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 May 31 to Jun 1
CA $226
CA $258 total
May 31 - Jun 1
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Clean room. Extremely friendly and helpful staff. Very family friendly. Overall a great experience."
Reviewed on May 23, 2026
Hotel Indigo Chicago-Vernon Hills by IHG
450 N Milwaukee Ave Vernon Hills IL
Fully refundable
The price is CA $151 per night from Jun 8 to Jun 9
CA $151
CA $167 total
Jun 8 - Jun 9
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 14 to Jun 15
CA $157
CA $175 total
Jun 14 - Jun 15
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.
