Winslow Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Winslow
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
€777
per person
20 Nov - 23 Nov
found 17 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
A wonderful hotel. The hotel is in a great location and very convenient. The breakfast is plentiful and delicious
Reviewed on 23 Sept 2026
Top hotels in Winslow
City Express By Marriott Freeport
1060 Riverside Dr Freeport IL
Fully refundableReserve now, pay when you stay
€104
4 Oct - 5 Oct
includes taxes & fees
8/10 Very good! (774 reviews)
"Plumbing leaks, poor continental breakfast, guest playing TV so loud at night it woke me up 2 times, ice machine broke, coffee machine broke"
Reviewed on 22 Sept 2026
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundableReserve now, pay when you stay
€106
18 Oct - 19 Oct
includes taxes & fees
9/10 Wonderful! (947 reviews)
"Good breakfast!"
Reviewed on 22 Sept 2026
Eugene Hotel
1517 11th St Monroe WI
Fully refundableReserve now, pay when you stay
€123
24 Sept - 25 Sept
includes taxes & fees
9.6/10 Exceptional! (20 reviews)
"The eugene hotel was new and clean. Coffee in the rooms weren't good. Needed more hooks in the bathroom. But overall would stay again , they just need to get a few of the twerks taken care of. Wish they would have had fresh coffee in lobby"
Reviewed on 21 Sept 2026
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.
Frequently asked questions
How much does a Winslow holiday package cost?
You'll find cheap prices from €748 on Expedia for your Winslow escape. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Winslow costs.
What are the cheapest months to go to Winslow?
You can usually find reduced prices and better availability in January, February and November. Explore our cheap Winslow holiday packages and you could land some excellent off-season deals.
How many days is enough for Winslow?
With a well-organised travel plan, you can easily tick off the most popular Winslow sights in a few days. But if you'd like to venture off the beaten track or go on day trips, think about booking your Winslow holiday for longer.
How to find the best Winslow package deals?
Use Expedia's filter tool to find some fabulous Winslow package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Winslow package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package as early as possible.
Is it cheaper to book a Winslow holiday as a package?
You can enjoy significant savings on your next Winslow retreat by booking a tailored holiday package. Click on the "Package" heading, then select your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Winslow?
If you have your Winslow travel dates finalized, book early to score some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Winslow?
- Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Winslow.
- Plan your budget wisely: Besides the price of your stay, you'll need to consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that could arise during your trip to Winslow.
- Decide your trip length: Consider how much time you want to spend discovering Winslow. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
- Bundle your accommodation and airfare: Once you've nailed down your travel dates and duration, book the right Winslow holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
