Winthrop Harbor Trips (flight + hotel)

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Top hotels in Winthrop Harbor

Motel Sun Inn
Motel Sun Inn
2.5 out of 5
301 Sheridan Road, Winthrop Harbor, IL
Fully refundableReserve now, pay when you stay
6.6/10 (224 reviews)
"It was comfortable, I would stay again, but i do not like the $100 deposit plus paying for the room. The deposit was for in case I smoked in the room. They need to get rid of that."

Reviewed on Jun 30, 2025

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Motel Sun Inn
LA VILLA MOTEL
LA VILLA MOTEL
2 out of 5
1401 Sheridan Rd, Winthrop Harbor, IL
Fully refundable
The price is P3,459 per night from Jul 21 to Jul 22
P3,459
P4,012 total
Jul 21 - Jul 22
includes taxes & fees
6.2/10 (35 reviews)
"Clean and quick"

Reviewed on Jun 1, 2025

LA VILLA MOTEL
DoubleTree by Hilton Libertyville - Mundelein
DoubleTree by Hilton Libertyville - Mundelein
4 out of 5
510 E IL Route 83, Mundelein, IL
Fully refundableReserve now, pay when you stay
The price is P6,457 per night from Jul 20 to Jul 21
P6,457
P7,166 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
"Great place to stay for a quick visit. Clean"

Reviewed on Jul 6, 2025

DoubleTree by Hilton Libertyville - Mundelein
See all 603 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.

Frequently asked questions

How much does a Winthrop Harbor vacation package cost?
You'll find cheap prices on Expedia for your Winthrop Harbor getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Winthrop Harbor costs.
What are the cheapest months to go to Winthrop Harbor?
If you're looking to score a cheap Winthrop Harbor vacation package, consider traveling 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 Harbor?
Typically, a handful of days is enough to see the major attractions during your Winthrop Harbor vacation. 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 Harbor package deals?
Landing a cheap Winthrop Harbor 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 Harbor 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 Harbor vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations individually. Better still, you can customize your Winthrop Harbor 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 vacation package to Winthrop Harbor?
If you're planning an impromptu Winthrop Harbor 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 Harbor?

  1. Choose your travel dates: The things you'd like to do in Winthrop Harbor and your preferred season can help you decide when to go.
  2. 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 Harbor.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you want to experience in Winthrop Harbor. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your airfare and accommodations: After you've settled on your dates and duration, book the right Winthrop Harbor 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.