Winthrop Harbor Vacation Packages

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Top Winthrop Harbor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,153, price is now CA $1,484 per person
CA $1,484
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Mediocre all around and for the price point not worth it. Great location. But nothing else compelling. Food was only ok. Service was only ok. Nothing memorable. Will seek somewhere else next time.

Reviewed on Jul 8, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $3,926, price is now CA $2,363 per person
CA $2,363
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
I liked everything except that the air conditioner in the hotel hallway was too cold

Reviewed on Jul 8, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $7,380, price is now CA $4,994 per person
CA $4,994
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on Jul 8, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,290, price is now CA $1,614 per person
CA $1,614
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location. The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.

Reviewed on Jul 6, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $3,176, price is now CA $2,335 per person
CA $2,335
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
View was beautiful, accommodations were excellent.

Reviewed on Jul 8, 2026

Ready to book your vacation to Winthrop Harbor?

 

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Winthrop Harbor Hotel Deals

LA VILLA MOTEL

LA VILLA MOTEL

2 out of 5
1401 Sheridan Rd Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Jul 14 to Jul 15
CA $87
CA $101 total
Jul 14 - Jul 15
includes taxes & fees
6.8/10 (73 reviews)
"Dirty and moldy"

Reviewed on Jun 30, 2026

LA VILLA MOTEL
Motel Sun Inn

Motel Sun Inn

2.5 out of 5
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from Aug 9 to Aug 10
CA $93
CA $108 total
Aug 9 - Aug 10
includes taxes & fees
6.8/10 (281 reviews)
"The staff were so nice! The rooms and bathroom were so clean. The building is a little older but everything was in good shape. Free WiFi use and the air conditioner worked perfectly. The price was also fair. It was 90 dollars and a 50 dollar deposit fee but you get the 50 dollars back in your account ..."

Reviewed on Jun 25, 2026

Motel Sun Inn
Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
1700 Nations Dr Gurnee IL
The price is CA $263 per night from Aug 9 to Aug 10
CA $263
CA $300 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,016 reviews)
"The food at Buckets was bad! The fries were constantly cold and hard and not fresh! The burger was cold! All the food tasted old and was expensive! The drinking system is such a scam! You can barely fill your cup! It's so many people in the pools the water looks yucky I didn't even want to go in! ..."

Reviewed on Jul 8, 2026

Great Wolf Lodge Illinois
See all 681 properties in Winthrop Harbor
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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Stay near popular Winthrop Harbor attractions

North Point Marina Beach

Why not spend a lazy afternoon at North Point Marina Beach during your trip to Winthrop Harbor? While you're in the area, stroll along the beaches.
See properties

Frequently asked questions

How much does a Winthrop Harbour vacation package cost?
You can snap up a vacation package to this destination from CA $1,484 on Expedia. However, how much your vacation to Winthrop Harbour costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Winthrop Harbour?
You're likely to find reduced prices and better availability in January, February and March. Take a look at our cheap Winthrop Harbour vacation packages and you could get some great off-season discounts.
How many days is enough for Winthrop Harbour?
With a well-planned schedule, you can easily hit the main Winthrop Harbour sights in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Winthrop Harbour vacation for longer.
How to find the best Winthrop Harbour package deals?
Finding a cheap Winthrop Harbour package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most economical Winthrop Harbour package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Winthrop Harbour vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging hotels and flights separately. Better still, you can personalize your Winthrop Harbour getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Winthrop Harbour?
If you've got your Winthrop Harbour vacation dates locked in, book as soon as you can to score some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Winthrop Harbour?

  1. Pick your travel dates: What you plan to do in Winthrop Harbour and your favourite season will help you decide when to go.
  2. Set a budget: Consider expenses like food, flights and transportation when calculating how much to set aside for your trip to Winthrop Harbour. Then, pick a property that works with your budget, whether that's a low-cost stay or a deluxe retreat.
  3. Determine how many days away: Start by listing all the attractions you'd like to get to in Winthrop Harbour. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your accommodations and airfare: After you've settled on your dates and duration, book the right Winthrop Harbour vacation package for you.

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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.