Winslow Holidays

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    Save up to €900 when you book a flight and hotel together*

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Top Flight + Hotel Deals in Winslow

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was €1,291, price is now €1,188 per person
€1,188
per person
30 Dec - 1 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,374, price is now €1,241 per person
€1,241
per person
30 Dec - 1 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
The room was extremely cold. Heater worked fine, but there was a leak in the sealant on the window, so throughout the night very cold air was coming in. Other than that it was fine for a one night stay

Reviewed on 7 Nov 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was €1,328, price is now €1,236 per person
€1,236
per person
30 Dec - 1 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,181 reviews)
The staff was very friendly and helpful.

Reviewed on 7 Nov 2026

Top hotels in Winslow

Eugene Hotel

Eugene Hotel

2 out of 5
1517 11th St Monroe WI
Fully refundableReserve now, pay when you stay
The price is €106 per night from 15 Nov to 16 Nov
€106
15 Nov - 16 Nov
includes taxes & fees
9.4/10 Exceptional! (44 reviews)
"Very nice rooms, right by the town square. Definitely would stay again!"

Reviewed on 6 Nov 2026

Eugene Hotel
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 €104 per night from 15 Nov to 16 Nov
€104
15 Nov - 16 Nov
includes taxes & fees
Country Inn & Suites by Radisson, Freeport, 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 €89 per night from 7 Dec to 8 Dec
€89
7 Dec - 8 Dec
includes taxes & fees
Super 8 by Wyndham Freeport
See all 107 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.

Frequently asked questions

How much does a Winslow holiday package cost?
You'll find cheap prices from €1,188 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.