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
CA $844
per person
Oct 30 - Nov 1
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested.
Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary hassle to do due to poor internet connection. Confusing amenity fees that I thought I was properly taking advantage of but toward the end felt was taking advantage of me to extract more money. I requested some items be brought up to our room only for staff to tell me I had to come down to the lobby myself to grab them.
Ultimately I can summarize the experience easily as its not worth what I paid for. Also no pool but thats more on me for not checking for that ahead of time.
Reviewed on Aug 26, 2026
Four Seasons Hotel Chicago
Downtown Chicago
CA $1,950
per person
Nov 5 - Nov 8
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Amazing hotel in excellent location. We loved our stay and hope to return for another trip to Chicago.
Reviewed on Aug 23, 2026
Ready to book your vacation to Winthrop Harbor?
Winthrop Harbor Hotel Deals
LA VILLA MOTEL
1401 Sheridan Rd Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
CA $78
CA $91 total
Sep 1 - Sep 2
includes taxes & fees
6.6/10 (80 reviews)
"Don't bother."
Reviewed on Aug 24, 2026
Motel Sun Inn
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
CA $91
CA $106 total
Aug 30 - Aug 31
includes taxes & fees
7/10 Good! (291 reviews)
"It was clean and staff was friendly"
Reviewed on Aug 24, 2026
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
Fully refundableReserve now, pay when you stay
CA $100
CA $112 total
Aug 31 - Sep 1
includes taxes & fees
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.
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.
North Point Marina
Explore the waterfront in Winthrop Harbor with a trip to North Point Marina. While you're in the area, stroll along the beaches.
Spring Bluff Forest Preserve
You can take time to visit Spring Bluff Forest Preserve during your travels to Winthrop Harbor. While you're in the area, stroll along the beaches.
Winthrop Harbor Village Hall
After visiting Winthrop Harbor Village Hall, make a plan to see the other sights and activities in Winthrop Harbor. While you're in the area, stroll along the beaches.
Frequently asked questions
How much does a Winthrop Harbour vacation package cost?
You can snap up a vacation package to this destination from CA $844 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?
- Pick your travel dates: What you plan to do in Winthrop Harbour and your favourite season will help you decide when to go.
- 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.
- 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.
- Combine your accommodations and airfare: After you've settled on your dates and duration, book the right Winthrop Harbour vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
