Winthrop Harbor Holidays from AU$574

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

The Latest Winthrop Harbor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Price was AU$679, price is now AU$574 per person
AU$574
per person
22 Jan - 25 Jan
found 24 hours ago
Return flight included
Los Angeles (QLA) to Chicago (ORD)
9/10 Wonderful! (3,188 reviews)

Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
Price was AU$839, price is now AU$675 per person
AU$675
per person
22 Jan - 25 Jan
found 24 hours ago
Return flight included
Los Angeles (QLA) to Chicago (ORD)
8.8/10 Excellent! (1,390 reviews)

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
Price was AU$731, price is now AU$591 per person
AU$591
per person
22 Jan - 25 Jan
found 24 hours ago
Return flight included
Los Angeles (QLA) to Chicago (ORD)
9.4/10 Exceptional! (1,106 reviews)
Had a great time and the place had a great breakfast and staff!

Reviewed on 30 Oct 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was AU$753, price is now AU$628 per person
AU$628
per person
22 Jan - 25 Jan
found 24 hours ago
Return flight included
Los Angeles (QLA) to Chicago (ORD)
8.6/10 Excellent! (2,885 reviews)

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
Price was AU$705, price is now AU$604 per person
AU$604
per person
22 Jan - 25 Jan
found 24 hours ago
Return flight included
Los Angeles (QLA) to Chicago (ORD)
7.6/10 Good! (1,864 reviews)

Winthrop Harbor Holiday

Winthrop Harbour Essential Information

Language
English
Currency
U.S dollars
Population
6,800
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC

Our pick of the best Winthrop Harbor Hotel Deals

LA VILLA MOTEL

LA VILLA MOTEL

2 out of 5
1401 Sheridan Rd Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
The price is AU$101 per night from 12 Nov to 13 Nov
AU$101
12 Nov - 13 Nov
includes taxes & 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
The price is AU$98 per night from 30 Nov to 1 Dec
AU$98
30 Nov - 1 Dec
includes taxes & fees
7/10 Good! (300 reviews)
"Perfect and they have Jacuzzi"

Reviewed on 14 Oct 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
The price is AU$106 per night from 3 Nov to 4 Nov
AU$106
3 Nov - 4 Nov
includes taxes & fees
8/10 Very good! (1,863 reviews)
"Rooms are clean, staff was excellent, breakfast was good, and the pool/hot tub are superior. We will be back!"

Reviewed on 30 Oct 2026

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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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

Frequently asked questions

How much does a Winthrop Harbour holiday package cost?
You'll find cheap prices from AU$574 on Expedia for your Winthrop Harbour getaway. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Winthrop Harbour costs.
What are the cheapest months to go to Winthrop Harbour?
If you're looking to score a cheap Winthrop Harbour holiday package, consider travelling 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 Harbour?
Typically, a handful of days is enough to see the major attractions during your Winthrop Harbour holiday. 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 Harbour package deals?
Landing a cheap Winthrop Harbour 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 Harbour 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 Harbour holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and accommodation individually. Better still, you can customise your Winthrop Harbour 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 holiday package to Winthrop Harbour?
If you're planning an impromptu Winthrop Harbour 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 Harbour?

  1. Choose your travel dates: The things you'd like to do in Winthrop Harbour and your preferred season can help you decide when to go.
  2. 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 Harbour.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you want to experience in Winthrop Harbour. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your airfare and accommodation: After you've settled on your dates and duration, book the right Winthrop Harbour holiday package for you.

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