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 $1,432, price is now CA $1,041 per person
CA $1,041
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Was a little noisy but I think that was just my unit. Facilities were top notch!
Reviewed on Apr 4, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,815, price is now CA $1,156 per person
CA $1,156
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Beautiful rooms at an amazing location. Parking is terribly expensive though, and breakfast is not included. There is no mini fridge, so good luck saving leftovers to reduce expenses. There is also no swimming pool which I found weird for a place this elegant.
Their main restaurant does not have good breakfast. Go for dinner or lunch and you will be very happy. But don't bother with breakfast, it's just a bunch of cheese and grease and it's unpleasant.
Reviewed on Apr 4, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,105, price is now CA $1,471 per person
CA $1,471
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 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 $166 per night from Apr 12 to Apr 13
CA $166
CA $189 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (1,011 reviews)
Family of four, girls are 9 and 14. We go to different great wolf lodges. This one wasnt bad, two attractions were closed temporarily due to kids puking. Be present with your kids, go on the water slides, tube the lazy river, get smoked by big waves in the wave pool. Sad seeing all the parents on ...
Reviewed on Apr 4, 2026
Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Apr 12 to Apr 13
CA $119
CA $142 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
Great people. Comfy bed. Nice HOT hot tub. Great breakfast.
Reviewed on Apr 5, 2026
Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant
13340 Hospitality Ct Mount Pleasant WI
Fully refundableReserve now, pay when you stay
The price is CA $88 per night from Apr 12 to Apr 13
CA $88
CA $100 total
Apr 12 - Apr 13
includes taxes & fees
8.2/10 Very Good! (503 reviews)
Everything was nice
Reviewed on Mar 31, 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.
