Winthrop Harbor Holidays from £669

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Top Winthrop Harbor Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,050, price is now £669 per person
£669
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable

Reviewed on 17 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,730, price is now £1,041 per person
£1,041
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,385, price is now £839 per person
£839
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,580, price is now £984 per person
£984
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
Shawn at the front desk was awesome. It was our first time in Chicago and we loved staying at LondonHouse!

Reviewed on 19 Aug 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,263, price is now £806 per person
£806
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Friendly staff, clean and comfortable, convenient location

Reviewed on 20 Aug 2025

Winthrop Harbour Essential Information

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

Top hotels in Winthrop Harbor

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 £51 per night from 21 Aug to 22 Aug
£51
21 Aug - 22 Aug
includes taxes & fees
6.6/10 (252 reviews)
"Pleasantly surprised."

Reviewed on 17 Aug 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 £51 per night from 28 Aug to 29 Aug
£51
28 Aug - 29 Aug
includes taxes & fees
6.4/10 (45 reviews)
"Good"

Reviewed on 13 Aug 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 £90 per night from 26 Aug to 27 Aug
£90
26 Aug - 27 Aug
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"Nice place ,clean , good service"

Reviewed on 16 Aug 2025

DoubleTree by Hilton Libertyville - Mundelein
See all 585 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

Why should I book my Winthrop Harbour holiday with Expedia?
With top-value flights, accommodation and car hire options all in one place, Expedia makes arranging your Winthrop Harbour break hassle-free. Moreover, we can help you bundle your bookings into a package holiday so you can save even more. Select from wonderful retreats, add your flights and/or a car hire (and maybe even some fun tours and activities!) and score unbeatable prices. Need to change your plans? Expedia has a flexible cancellation policy for many bookings. To learn more, check out our Customer Service Portal link.
When is the best time of year to holiday in Winthrop Harbour?
To enjoy the buzz of peak season, pack your bags for May, June and July. December, January and February are generally quieter and a smart idea if you want to get away from the crowds. To give you an idea of what type of weather you can experience, the daytime average temperature in January, the coolest time of year in Winthrop Harbour, is -4ºC. The warmest time here is July, when temperatures are around 22ºC.
What is the top hotel for my holiday in Winthrop Harbour?
Put your feet up and relax in comfort in Winthrop Harbour by choosing Hilton Garden Inn Lake Forest Mettawa as your home-away-from-home and gateway to exploration.
How do I get a cheap holiday to Winthrop Harbour?
Bundle your flights and hotels, add extras such as activities or a hire car, and save with a Winthrop Harbour holiday. You won't just walk away with big discounts on your adventure — you'll have plenty of choice too. When you book through Expedia, you'll have your pick of over 400 airlines and 321,000 hotels globally. Your next big adventure starts right here, right now! Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
Do I need a visa for my Winthrop Harbour holiday?
Visa requirements for Winthrop Harbour vary depending on your nationality and purpose of your visit. Remember to check official government websites to determine if you need a visa for your trip. They'll also give you the most up-to-date information, including details about application procedures and any supporting documentation that might be necessary. Enquire about your visa requirements well in advance to ensure a smooth travel experience. Finally, make sure your passport has at least six months validity from your planned date of return.
What should I wear on my Winthrop Harbour holiday?
Although everyone's personal style is different, it can help to have a few guidelines for what type of clothes to wear on your holiday in Winthrop Harbour. Consider browsing social media before leaving for inspiration on local dress codes or fashion trends. Pack your luggage with confidence by checking the forecast in Winthrop Harbour. July brings the warmest temperatures, with daily averages of 22ºC, while January days average -4ºC, making it the coolest month.
What does an Expedia Winthrop Harbour holiday include?
With Expedia, you can select a combination of flights, car hires and hotels to build your perfect Winthrop Harbour travel package. Once you've made your booking, simply add on all the fun stuff like sightseeing tours and activities. Don't forget — the more you bundle, the more you'll save! Private holiday homes and motels are two sought-after property types in Winthrop Harbour. No matter your holiday style or size of your group, you can rely on Expedia for the flexibility and freedom to tailor your next big adventure.
Does Expedia offer Book Now, Pay Later Winthrop Harbour holidays?
We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply select the payment plan that suits best during checkout and take the stress out of budgeting for your next trip. Make sure you bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: If paying across multiple transactions is what works best for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream getaway possible.
  • No-deposit holidays: Clicking on the "book now" button is much easier with this payment option. With no upfront fee for your getaway, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Winthrop Harbour Expedia holiday?
The choice is all yours! We have access to over 400 airlines around the world, so you can customise your Winthrop Harbour adventure according to your budget and style.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.