Winthrop Harbor Holidays from £1,140

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Top Winthrop Harbor Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was £1,561, price is now £1,140 per person
£1,140
per person
30 Sept - 5 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
The room was amazing! It was spacious and clean. The staff were helpful and very considerate. The hotel is located in an ideal location, right off of Michigan Avenue, in the heart of downtown. Shopping and restaurants are within short walking distances.

Reviewed on 8 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,035, price is now £1,325 per person
£1,325
per person
11 Sept - 16 Sept
found 2 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location. The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.

Reviewed on 6 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,231, price is now £1,589 per person
£1,589
per person
30 Sept - 5 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We had our room upgraded to a suite which was a nice surprise. It was a great stay!

Reviewed on 8 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,696, price is now £1,242 per person
£1,242
per person
30 Sept - 5 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,886, price is now £1,384 per person
£1,384
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on 8 Jul 2026

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

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 £53 per night from 16 Jul to 17 Jul
£53
16 Jul - 17 Jul
includes taxes & fees
6.8/10 (73 reviews)
"Dirty and moldy"

Reviewed on 30 Jun 2026

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 £57 per night from 4 Aug to 5 Aug
£57
4 Aug - 5 Aug
includes taxes & fees
6.8/10 (281 reviews)
"The staff were so nice! The rooms and bathroom were so clean. The building is a little older but everything was in good shape. Free WiFi use and the air conditioner worked perfectly. The price was also fair. It was 90 dollars and a 50 dollar deposit fee but you get the 50 dollars back in your account ..."

Reviewed on 25 Jun 2026

Motel Sun Inn
Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
1700 Nations Dr Gurnee IL
The price is £158 per night from 9 Aug to 10 Aug
£158
9 Aug - 10 Aug
includes taxes & fees
8.6/10 Excellent! (1,016 reviews)
"The food at Buckets was bad! The fries were constantly cold and hard and not fresh! The burger was cold! All the food tasted old and was expensive! The drinking system is such a scam! You can barely fill your cup! It's so many people in the pools the water looks yucky I didn't even want to go in! ..."

Reviewed on 8 Jul 2026

Great Wolf Lodge Illinois
See all 681 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.
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Stay near popular Winthrop Harbor attractions

North Point Marina Beach

Why not spend a lazy afternoon at North Point Marina Beach during your trip to Winthrop Harbor? While you're in the area, stroll along the beaches.
See properties

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.

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. Flight-inclusive packages are ATOL protected.