Winthrop Harbor Holidays from £1,016

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The Latest Winthrop Harbor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.6/10 Excellent! (1,781 reviews)
Great location and wonderful staff

Reviewed on 1 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.

Reviewed on 27 Jun 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Staff was very friendly and helpful. We had a great stay in every way possible!

Reviewed on 30 Jun 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Comfortable, stylish, friendly hotel in a fabulous location near Millennium Park, Art Institute, and Riverwalk. Friendly staff throughout but the cherry on top was Antoine who checked our bags and arranged out transportation to the airport when we checked out

Reviewed on 29 Jun 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
The service response and help I received from Shannon McKinney the Business Travel Sales Manager and Zachary at the concierge desk were exceptional! We had a transportation dilemma and Shannon worked with us and resolved it! The hotel location is excellent, right next to the train stop from Midway and everything we wanted.

Reviewed on 30 Jun 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.8/10 Excellent! (1,781 reviews)
The staff hospitality was incredible 💖

Reviewed on 2 Jul 2025

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

Motel Sun Inn
Motel Sun Inn
2.5 out of 5
301 Sheridan Road, Winthrop Harbor, IL
Stay at this motel in Winthrop Harbor. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Popular attractions Spring Bluff Forest Preserve and North Point ...
6.6/10 (223 reviews)
"It was comfortable, I would stay again, but i do not like the $100 deposit plus paying for the room. The deposit was for in case I smoked in the room. They need to get rid of that."

Reviewed on 30 Jun 2025

Motel Sun Inn
Hotel Indigo Chicago-Vernon Hills by IHG
Hotel Indigo Chicago-Vernon Hills by IHG
3.5 out of 5
450 N Milwaukee Ave, Vernon Hills, IL
Stay at this 3.5-star boutique hotel in Vernon Hills. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff in their reviews. ...
8.4/10 Very Good! (1,011 reviews)
"Rooms are interesting with the bathroom at the back and plenty of space upfront, the bathroom was just very small and the drain smelled bad.... the pool area smelled bad to me too. Also had to have our key cards reprogrammed multiple times but the staff was very helpful and friendly. The area is ..."

Reviewed on 1 Jul 2025

Hotel Indigo Chicago-Vernon Hills by IHG
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
Stay at this 3-star business-friendly hotel in Gurnee. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.8/10 Good! (1,221 reviews)
"in truth outside need care, i.e. bench for sitting, a pinic table also nice."

Reviewed on 30 Jun 2025

La Quinta Inn & Suites by Wyndham Chicago Gurnee
See all 603 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.