Winthrop Harbor Vacation Packages
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Top Winthrop Harbor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,498, price is now CA $980 per person
CA $980
per person
Jun 27 - Jul 1
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
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,231, price is now CA $1,411 per person
CA $1,411
per person
Aug 2 - Aug 7
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (474 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
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,574, price is now CA $1,063 per person
CA $1,063
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (116 reviews)
We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.
Reviewed on May 17, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,801, price is now CA $1,286 per person
CA $1,286
per person
Aug 8 - Aug 12
found 23 hours ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
Great location and very convenient to river walk and vicinity.
Reviewed on May 22, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,594, price is now CA $1,854 per person
CA $1,854
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Great experience! Would stay here agin
Reviewed on May 18, 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 26 to May 27
CA $226
CA $258 total
May 26 - May 27
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"Clean room. Extremely friendly and helpful staff. Very family friendly. Overall a great experience."
Reviewed on May 23, 2026
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jun 7 to Jun 8
CA $155
CA $172 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"The room was not great. The bed lamp was unplugged and there was no socket close to plug it in. So I had to get out of bed to use the lamps in front of the room. The toilet after every use had to be flushed 2-3 times. Where the vents were for the ac had broken wood around it. It was not a great room. ..."
Reviewed on May 18, 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 May 31 to Jun 1
CA $151
CA $167 total
May 31 - Jun 1
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"The room was nice but the he shower floor was slippery which is an accident waiting to happen."
Reviewed on May 23, 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.
