Winslow Holidays from £917

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    Packages with flights are ATOL protected

Your Winslow Holiday

Memorable adventures await when you reserve a holiday package to Winslow. Whether you're a foodie, history buff or just a traveller who loves to discover new places, there's something for everyone in this awesome city. Any trip to Winslow has to include a little sightseeing. Lake Le Aqua Na State Park is a great place to begin exploring. Stop daydreaming and start travelling. Check out the range of options on Expedia today and put your Winslow holiday plans into motion!

Top Winslow Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
23 Sept - 26 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Excellent establishment great staff very clean and spacious

Reviewed on 5 Aug 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
23 Sept - 26 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on 26 Jul 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
22 Oct - 29 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on 3 Aug 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
22 Oct - 29 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (270 reviews)
walkable to many desireable places.

Reviewed on 16 Jul 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
15 Oct - 22 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (332 reviews)
A lot of good food options walkable distance.

Reviewed on 3 Aug 2025

Winslow Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Lake Le Aqua Na State Park, Famous Fossil Winery and Stagecoach Golf Course

Top hotels in Winslow

Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport

2 out of 5
1551 Sleezer Home Rd, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is £60 per night from 17 Aug to 18 Aug
£60
17 Aug - 18 Aug
includes taxes & fees
6.8/10 (332 reviews)
"Friendly staff, clean room , loved the shower . It was the perfect budget place to sleep for 2 nights and move on with our trip"

Reviewed on 29 Jul 2025

Super 8 by Wyndham Freeport
Country Inn & Suites by Radisson, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL

2.5 out of 5
1710 South Dirck Drive, Freeport, IL
Fully refundable
The price is £95 per night from 7 Sept to 8 Sept
£95
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (799 reviews)
"Nice place"

Reviewed on 4 Aug 2025

Country Inn & Suites by Radisson, Freeport, IL
Hampton Inn Freeport

Hampton Inn Freeport

2.5 out of 5
109 S Galena Ave, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is £91 per night from 17 Aug to 18 Aug
£91
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (439 reviews)
"Good"

Reviewed on 3 Aug 2025

Hampton Inn Freeport
See all 97 properties in Winslow
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

How much does a Winslow travel package cost?
Starting from a low £917, a travel package is your gateway to low-cost travel. Customize your Winslow trip by choosing from our comprehensive range of hotels, flights and rental cars.
If I'm not able to travel, can I cancel my Winslow travel package?
Whether it's your hotel or flight, you can cancel or change it. Locked in your Winslow travel package in the last 24 hours? You may be able to make changes for free. If it's been longer than that, you may incur a fee from your airline, hotel or car rental company. For more information, visit our Customer Service Portal. We'll help you each step of the way.
How do I get a cheap travel package to Winslow?
Book everything in the one place with our Winslow holiday packages. You'll find deals on flights, hotels, tours and more that'll keep your wallet happy and your adventurous spirit busy. And, with more than 550 airlines and 1,000,000 hotel options across the globe to select from, you have countless opportunities to mix and match all you want.
Does Expedia offer Book Now, Pay Later Winslow holidays?
We sure do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply select the payment plan that suits you best during the checkout process and take away the stress of budgeting for your trip. Make sure you bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay off your holiday across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that "book now" button, choose a low deposit holiday payment plan with Klarna.

What are the top hotels in Winslow?
Get your escape off to an excellent start by reserving a room at Hyatt Regency Chicago. It's one of most sought-after hotels in Winslow. Another top option is The Godfrey Hotel Chicago.
How far in advance should I book my Winslow holiday?
Browse Expedia to compare international fares as soon as you know your travel dates. In most cases, you can purchase a seat up to a year in advance. If you can't see your preferred carrier, or you have to book last minute, fear not. The lowest prices to Winslow sometimes appear a few weeks before the date of departure.
What does an Expedia Winslow travel package include?
Travel packages include flights, hotels and rental cars, but you can combine any of them to create your ideal Winslow trip. You can also add on activities and experiences once you've made your booking. You're in the driver's seat! When you bundle your bookings with Expedia, you'll enjoy discounts you won't find anywhere else.
What should I know before booking a Winslow travel package?
Whether it's relaxation or adventure you're chasing, a Winslow travel package lets you organise your escape your way. Plus, you'll score great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Winslow Expedia travel package?
With a travel package, you're the one in charge. Whether you're looking to fly to Winslow in economy or business class, simply pick from the available airline options. Expedia has access to over 550 airline partners throughout the world.

* 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.