Winthrop Harbor Vacations from $308

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The Latest Winthrop Harbor vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $459, price is now $308 per person
$308
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
Everything was really nice. But we didn't have room service. And the sink had been clogged since the day we arrived.

Reviewed on Nov 1, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $606, price is now $398 per person
$398
per person
Dec 16 - Dec 19
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $601, price is now $404 per person
$404
per person
Jan 21 - Jan 24
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $766, price is now $517 per person
$517
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $804, price is now $547 per person
$547
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Estuvo muy increíble, fue una experiencia maravillosa.Es un lugar precioso me encantó

Reviewed on Nov 1, 2026

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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

Winthrop Harbor Hotel Deals

LA VILLA MOTEL

LA VILLA MOTEL

2 out of 5
1401 Sheridan Rd Winthrop Harbor IL
Fully refundable
$61 nightly
The price is $71 total per night from Nov 9 to Nov 10
$71 total
Nov 9 - Nov 10
Total with taxes and 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
$66 nightly
The price is $77 total per night from Nov 3 to Nov 4
$77 total
Nov 3 - Nov 4
Total with taxes and 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
$67 nightly
The price is $75 total per night from Nov 10 to Nov 11
$75 total
Nov 10 - Nov 11
Total with taxes and fees
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.

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 $308 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.