Winthrop Harbor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Winthrop Harbor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $822, price is now CA $527 per person
CA $527
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (335 reviews)
Great except parking

Reviewed on Aug. 19, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,684, price is now CA $1,017 per person
CA $1,017
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug. 19, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,636, price is now CA $1,008 per person
CA $1,008
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,540, price is now CA $973 per person
CA $973
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug. 22, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $1,754, price is now CA $1,127 per person
CA $1,127
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug. 12, 2025

Ready to book your vacation to Winthrop Harbor?

 

Choose your dates

Winthrop Harbor Hotel Deals

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 CA $82 per night from Aug 25 to Aug 26
CA $82
CA $95 total
Aug 25 - Aug 26
includes taxes & fees
6.6/10 (253 reviews)
"Pleasantly surprised."

Reviewed on Aug. 17, 2025

Motel Sun Inn
LA VILLA MOTEL

LA VILLA MOTEL

2 out of 5
1401 Sheridan Rd, Winthrop Harbor, IL
Fully refundable
The price is CA $82 per night from Sep 1 to Sep 2
CA $82
CA $96 total
Sep 1 - Sep 2
includes taxes & fees
6.4/10 (45 reviews)
"Good"

Reviewed on Aug. 13, 2025

LA VILLA MOTEL
DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

4 out of 5
510 E IL Route 83, Mundelein, IL
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Sep 1 to Sep 2
CA $152
CA $168 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
Great place to stay
"The staff was amazing, very helpful and friendly. The room was very comfortable, but needed some repair (Wallpaper peeling in multiple area's). The pool area is very spacious. The lobby is nice and accommodating with no rooms at that end so noise was not an issue."

Reviewed on Aug. 23, 2025

DoubleTree by Hilton Libertyville - Mundelein
See all 586 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Winthrop Harbour vacation package cost?
You can snap up a vacation package to this destination from CA $527 on Expedia. However, how much your vacation to Winthrop Harbour costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Winthrop Harbour?
You're likely to find reduced prices and better availability in January, February and March. Take a look at our cheap Winthrop Harbour vacation packages and you could get some great off-season discounts.
How many days is enough for Winthrop Harbour?
With a well-planned schedule, you can easily hit the main Winthrop Harbour sights in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Winthrop Harbour vacation for longer.
How to find the best Winthrop Harbour package deals?
Finding a cheap Winthrop Harbour package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most economical Winthrop Harbour package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Winthrop Harbour vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging hotels and flights separately. Better still, you can personalize your Winthrop Harbour getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Winthrop Harbour?
If you've got your Winthrop Harbour vacation dates locked in, book as soon as you can to score some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Winthrop Harbour?

  1. Pick your travel dates: What you plan to do in Winthrop Harbour and your favourite season will help you decide when to go.
  2. Set a budget: Consider expenses like food, flights and transportation when calculating how much to set aside for your trip to Winthrop Harbour. Then, pick a property that works with your budget, whether that's a low-cost stay or a deluxe retreat.
  3. Determine how many days away: Start by listing all the attractions you'd like to get to in Winthrop Harbour. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your accommodations and airfare: After you've settled on your dates and duration, book the right Winthrop Harbour 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.