Winthrop Harbor Vacations from ￥289,143

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The Latest Winthrop Harbor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥333,132, price is now ￥289,143 per person
￥289,143
per person
Dec 1 - Dec 6
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (3,148 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥488,460, price is now ￥369,491 per person
￥369,491
per person
Dec 1 - Dec 6
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
The location is in the heart of the city, Literally everything is walking distance My husband amd loved the hotel.

Reviewed on Oct 31, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was ￥402,562, price is now ￥338,667 per person
￥338,667
per person
Dec 1 - Dec 6
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
Staff was great and the room was clean!

Reviewed on Oct 29, 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 ￥387,925, price is now ￥335,542 per person
￥335,542
per person
Dec 1 - Dec 6
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
Incredible!!

Reviewed on Oct 31, 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was ￥373,285, price is now ￥329,536 per person
￥329,536
per person
Dec 1 - Dec 6
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,426 reviews)

Find the Best Winthrop Harbor Vacation Packages

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 ￥9,659 per night from Nov 2 to Nov 3
￥9,659
￥11,203 total
Nov 2 - Nov 3
includes taxes & fees
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 ￥9,359 per night from Nov 1 to Nov 2
￥9,359
￥10,854 total
Nov 1 - Nov 2
includes taxes & fees
7/10 Good! (300 reviews)
"Perfect and they have Jacuzzi"

Reviewed on Oct 14, 2026

Motel Sun Inn
La Quinta Inn & Suites by Wyndham Chicago Gurnee

La Quinta Inn & Suites by Wyndham Chicago Gurnee

3 out of 5
5688 Northridge Rd Gurnee IL
Fully refundableReserve now, pay when you stay
The price is ￥10,580 per night from Nov 2 to Nov 3
￥10,580
￥11,847 total
Nov 2 - Nov 3
includes taxes & fees
8/10 Very Good! (1,863 reviews)
"Rooms are clean, staff was excellent, breakfast was good, and the pool/hot tub are superior. We will be back!"

Reviewed on Oct 30, 2026

La Quinta Inn & Suites by Wyndham Chicago Gurnee
See all 678 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.

Stay near popular Winthrop Harbor attractions

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.
See properties

Frequently asked questions

How much does a Winthrop Harbor vacation package cost?
You'll find cheap prices from ￥289,143 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.