Winthrop Harbor Vacations from ￥210,352
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The Latest Winthrop Harbor Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥210,352
per person
Nov 9 - Nov 13
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Excelente localización, habitaciones muy amplias, funcionales y nada ruidosas.
Personal muy atento y servicial.
Rooftop gran atracción de la ciudad
Reviewed on Sep 15, 2026
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
￥307,398
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (3,269 reviews)
Great weekend stay. Everything was amazing, down to location of getting around in the city. The ONLY downside was the cost of parking. It’s valet only and the price was not listed anywhere. It’s $88 a night if you’re doing overnight.
Reviewed on Sep 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
￥219,368
per person
Nov 9 - Nov 13
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)
We were so excited about spending the time at Sable hotel however, when we arrived, it was the House of horrors. It was very filthy. Went to go grab an extra blanket and a butt plug fell out of it. Asked for them to please come clean the room they said housekeeping was not there and would take care of it tomorrow so we spent the first night in a filthy dirty room as they had no extra room rooms due to multiple concerts being held that weekend. My advice the location is great, but there’s other options that are more affordable.
Reviewed on Sep 14, 2026
Find the Best Winthrop Harbor Vacation Packages
Winthrop Harbor Hotel Deals
LA VILLA MOTEL
1401 Sheridan Rd Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
￥9,417
￥10,922 total
Sep 28 - Sep 29
includes taxes & fees
6.6/10 (81 reviews)
"Clean"
Reviewed on Aug 29, 2026
Motel Sun Inn
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
￥10,092
￥11,706 total
Sep 16 - Sep 17
includes taxes & fees
7/10 Good! (294 reviews)
"Clean easy check in very"
Reviewed on Sep 14, 2026
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
Fully refundableReserve now, pay when you stay
￥16,696
￥18,529 total
Oct 4 - Oct 5
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Great place to stay!"
Reviewed on Sep 15, 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
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.
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.
Frequently asked questions
How much does a Winthrop Harbor vacation package cost?
You'll find cheap prices from ￥210,352 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?
- 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.
- 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.
- 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.
- 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.
