Winthrop Harbor Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Winthrop Harbor
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
€698
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Our shower head continually sprayed the bathroom floor. The shower curtain needed to be longer.
Reviewed on 22 Aug 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
€2,017
per person
8 Oct - 13 Oct
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (2,348 reviews)
Great hotel front desk very nice and informative close walking distance to public transportation and stores. If you don’t valet parking garages 1-2 blocks away for self parking.
Reviewed on 22 Aug 2026
Top hotels in Winthrop Harbor
LA VILLA MOTEL
1401 Sheridan Rd Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
€61
27 Aug - 28 Aug
includes taxes & fees
Motel Sun Inn
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
€65
24 Aug - 25 Aug
includes taxes & fees
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
Fully refundableReserve now, pay when you stay
€67
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (1,818 reviews)
"Does not deserve the very good review posted. So out dated."
Reviewed on 22 Aug 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.
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.
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.
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.
Frequently asked questions
How much does a Winthrop Harbour holiday package cost?
You'll find cheap prices from €698 on Expedia for your Winthrop Harbour getaway. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Winthrop Harbour costs.
What are the cheapest months to go to Winthrop Harbour?
If you're looking to score a cheap Winthrop Harbour holiday package, consider travelling in January, February and March. You'll generally find lower rates on hotels and airfares during these quieter months — perfect for a budget-friendly break.
How many days is enough for Winthrop Harbour?
Typically, a handful of days is enough to see the major attractions during your Winthrop Harbour holiday. However, if you'd like to have some time to kick back or go on day trips, think about extending your trip.
How to find the best Winthrop Harbour package deals?
Landing a cheap Winthrop Harbour package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most economical Winthrop Harbour package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winthrop Harbour holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and accommodation individually. Better still, you can customise your Winthrop Harbour trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Winthrop Harbour?
If you're planning an impromptu Winthrop Harbour getaway, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Winthrop Harbour?
- Choose your travel dates: The things you'd like to do in Winthrop Harbour and your preferred season can help you decide when to go.
- Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and experiences. Your hotel will likely be the largest expense during your trip to Winthrop Harbour.
- Set the duration of your trip: Start by compiling a list of the sights and activities you want to experience in Winthrop Harbour. Then, estimate how long you'll need at each, including any travel time.
- Bundle your airfare and accommodation: After you've settled on your dates and duration, book the right Winthrop Harbour holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
