Winthrop Harbor Vacations from $402
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The Latest Winthrop Harbor vacation packages
Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
$402
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,841 reviews)
It took 55 minutes to check in and then when I was taking a shower, the showerhead fell off and the water pressure almost knocked me down, and you had to wiggle the toilet to get us to stop
Reviewed on Oct 19, 2026
Swissotel - Chicago
Downtown Chicago
$558
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
I traveled from Cincinnati Ohio and the room on the 36th floor had a great view of Lake Michigan. Valet staff for parking was excellent as well. Highly recommended if you’re planning to visit Chicago.
Reviewed on Oct 19, 2026
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See all available trips from Houston to Winthrop Harbor
View all tripsStay 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.
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.
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.
Winthrop Harbor Hotel Deals
LA VILLA MOTEL
1401 Sheridan Rd Winthrop Harbor IL
Fully refundable
$61 nightly
$71 total
Oct 26 - Oct 27
Total with taxes and fees
Motel Sun Inn
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
$66 nightly
$77 total
Nov 1 - Nov 2
Total with taxes and fees
7/10 Good! (300 reviews)
"Perfect and they have Jacuzzi"
Reviewed on Oct 14, 2026
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
Fully refundableReserve now, pay when you stay
$110 nightly
$122 total
Nov 1 - Nov 2
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Breakfast was underwhelming. Cost was high for typical hotel breakfast which would be included at other places. There was loud rock music which made for a poor experience."
Reviewed on Oct 18, 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.
Find the Best Winthrop Harbor Vacation Packages
Winthrop Harbor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 6,800 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
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Frequently asked questions
How much does a Winthrop Harbor vacation package cost?
You'll find cheap prices from $402 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 hoping to book a cheap Winthrop Harbor vacation package, consider planning a trip in December, January and February. You'll usually find better prices on accommodations and flights during these months — perfect for budget-conscious travelers.
How many days is enough for Winthrop Harbor?
With a well-organized schedule, you can easily tick off the top Winthrop Harbor sights in a few days. But if you want to discover hidden gems or take day trips, think about booking your Winthrop Harbor vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Winthrop Harbor vacation packages?
Jet off on your perfect escape to Winthrop Harbor with Expedia's Book Now, Pay Later vacations. There's no need to save up or wait until payday — we've partnered with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up bargains before they disappear.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.