Winthrop Harbor Vacations from ￥251,912

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The Latest Winthrop Harbor Vacation Packages

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Sep 21 - Sep 25
found 9 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
The staff was so accommodating and extremely kind. Would stay here again 100%.

Reviewed on Aug 12, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 21 - Sep 25
found 9 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
It was exceptional all the way around

Reviewed on Aug 10, 2025

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,586 reviews)
We had corner king room and it was very nice! We saw the city and the pool. The only thing I didn’t like was no complimentary water and cookies like most hotels. Sometimes the water be on point after walking and traveling. It’s thoughtful.

Reviewed on Aug 12, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,084 reviews)
Very helpful and friendly staff

Reviewed on Aug 11, 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,830 reviews)
Pretty expensive but we managed without difficulty.

Reviewed on Aug 12, 2025

Find the Best Winthrop Harbor Vacation Packages

Winthrop Harbor Hotel Deals

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 (248 reviews)
Clean and quiet
"Convinately located to Fishing Harbors for Kenosha or Winthrop. Quite clean plenty of food options close by. I wish they could have coffee in the rooms or lobby. Great place for long wknd"

Reviewed on Aug 10, 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 ￥8,540 per night from Aug 20 to Aug 21
￥8,540
￥9,906 total
Aug 20 - Aug 21
includes taxes & fees
6.4/10 (41 reviews)
"Beautiful place. Would stay again"

Reviewed on Jul 20, 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 ￥16,125 per night from Sep 2 to Sep 3
￥16,125
￥17,895 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (1,013 reviews)
"Great location and nice area. We stayed on our way home from an event about 45 minutes away. The hotel is well maintained and has extras like a pool, workout room, restaurant/bar."

Reviewed on Aug 10, 2025

DoubleTree by Hilton Libertyville - Mundelein
See all 604 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 from ￥251,912 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.