Winthrop Harbor Vacations from $381

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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

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $668, price is now $381 per person
$381
per person
Jul 6 - Jul 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Breakfast was fresh and good

Reviewed on Apr 12, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $781, price is now $450 per person
$450
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Nice, but no microwave or refrigerator in room. Staff is nice and place was clean. Many things to do around.

Reviewed on Apr 11, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $836, price is now $502 per person
$502
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
The room was clean, spacious, with good views.

Reviewed on Apr 12, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $845, price is now $511 per person
$511
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Fantastic hotel in a great central location with helpful staff - what more could we ask for?!

Reviewed on Apr 11, 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
Save 100% on your flight
Price was $1,551, price is now $953 per person
$953
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast and parking not included

Reviewed on Apr 12, 2026

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Winthrop Harbor Hotel Deals

Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
1700 Nations Dr Gurnee IL
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $160 total per night from Apr 13 to Apr 14
$160 total
Apr 13 - Apr 14
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
The place was nice, but as a first tome visiter, it would have been better if they had given us or emailed me a map of the property. That especially would have been helpful when trying to find my room. We had kids with us, so i wanted to park as close to the room as possible. There were three towers ...

Reviewed on Apr 12, 2026

Great Wolf Lodge Illinois
Best Western Executive Inn Kenosha/Pleasant Prairie

Best Western Executive Inn Kenosha/Pleasant Prairie

2.5 out of 5
7220 122nd Ave Kenosha WI
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $102 total per night from Apr 19 to Apr 20
$102 total
Apr 19 - Apr 20
Total with taxes and fees
9/10 Wonderful! (1,008 reviews)
Breakfast was very good, lot of variety. Quiet.

Reviewed on Apr 12, 2026

Best Western Executive Inn Kenosha/Pleasant Prairie
Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant

Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant

2 out of 5
13340 Hospitality Ct Mount Pleasant WI
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $69 total per night from Apr 19 to Apr 20
$69 total
Apr 19 - Apr 20
Total with taxes and fees
8.2/10 Very Good! (506 reviews)
It seemed fresh. I have so many allergies I couldn't have anything besides the apple and a glass of juice. I was very disappointed that I was told I had 2 QN beds, I didn't. It was on the second floor with no elevator. I told them I can't do stairs and my friend had a knee-replacement. There was ...

Reviewed on Apr 9, 2026

Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant
See all 688 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 $381 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.