Winslow Holidays from £1,859

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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.
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
Price was £3,252, price is now £1,859 per person
£1,859
per person
17 Aug - 22 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
7.8/10 Good! (1,965 reviews)
Everything was Satisfactory

Reviewed on 6 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £4,028, price is now £2,259 per person
£2,259
per person
17 Aug - 22 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on 2 Jul 2026

Motel 6 Arlington Heights, IL - Chicago North Central

Motel 6 Arlington Heights, IL - Chicago North Central

2 out of 5
Price was £3,270, price is now £1,869 per person
£1,869
per person
17 Aug - 22 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8/10 Very good! (1,005 reviews)
Room was super clean and room was ready promptly. Love the energy of the staff at the front desk and they were super helpful. Nice play for a short stay

Reviewed on 4 Jul 2026

Motel 6 Villa Park, IL - Chicago West

Motel 6 Villa Park, IL - Chicago West

2 out of 5
Price was £3,276, price is now £1,872 per person
£1,872
per person
17 Aug - 22 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
6.8/10 (1,009 reviews)
Very dirty and not comfortable in anyway

Reviewed on 4 Jul 2026

Hyatt Place Itasca

Hyatt Place Itasca

3 out of 5
Price was £3,353, price is now £1,930 per person
£1,930
per person
17 Aug - 22 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (1,178 reviews)
Nice

Reviewed on 6 Jul 2026

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

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 £98 per night from 12 Jul to 13 Jul
£98
12 Jul - 13 Jul
includes taxes & fees
9/10 Wonderful! (911 reviews)
"Clean updated room. The staff was kind and helpful. The workout room was sufficient for my needs. Overall, very good room for the price with extremely easy check in and check out."

Reviewed on 6 Jul 2026

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

Country Inn & Suites by Radisson, Stockton, IL

2.5 out of 5
200 Dillon Ave Stockton IL
The price is £70 per night from 2 Aug to 3 Aug
£70
2 Aug - 3 Aug
includes taxes & fees
8.4/10 Very good! (681 reviews)
"The location is great and parking is easy. Lobby was clean and front desk staff very friendly. There was a roped off area in front of the main entrance door and the elevator was broken. The room has been updated, but isn't the cleanest. The main hall carpet is really run down. Our toilet srst was ..."

Reviewed on 27 Jun 2026

Country Inn & Suites by Radisson, Stockton, IL
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 £74 per night from 2 Aug to 3 Aug
£74
2 Aug - 3 Aug
includes taxes & fees
7/10 Good! (373 reviews)
"My stay was good. My only request is updating lamps or an outlet to allow for charging with USB ports. I haven’t stayed any place in awhile that didn’t have this in rooms."

Reviewed on 3 Jul 2026

Super 8 by Wyndham Freeport
See all 104 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 £1,859, 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.

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.