Winslow Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, 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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,291, price is now €824 per person
€824
per person
20 Sept - 26 Sept
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone there was friendly and gave us a lot of places to go eat for our one year anniversary

Reviewed on 21 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,927, price is now €1,160 per person
€1,160
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,701, price is now €1,044 per person
€1,044
per person
20 Sept - 26 Sept
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.

Reviewed on 17 Aug 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,420, price is now €926 per person
€926
per person
20 Sept - 26 Sept
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!

Reviewed on 18 Aug 2025

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was €1,276, price is now €844 per person
€844
per person
4 Oct - 10 Oct
just found
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,621 reviews)
Check in was easy and it felt very safe. Room was clean and was good sized for a Chicago hotel.

Reviewed on 21 Aug 2025

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 €74 per night from 21 Sept to 22 Sept
€74
21 Sept - 22 Sept
includes taxes & fees
6.8/10 (334 reviews)
"Local"

Reviewed on 16 Aug 2025

Super 8 by Wyndham Freeport
AmericInn by Wyndham Monroe

AmericInn by Wyndham Monroe

2.5 out of 5
424 4th Ave, Monroe, WI
Fully refundableReserve now, pay when you stay
The price is €105 per night from 7 Sept to 8 Sept
€105
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (362 reviews)
"Nice place to stay. We didn't like that you rent out the pool so it was full of kids and families that were not staying at the hotel. We tried using the pool and hot tub but it was so loud with kids we left. One of the reason we stayed was so we could use the pool and hot tub. Kitchen lady was lovely!! ..."

Reviewed on 19 Aug 2025

AmericInn by Wyndham Monroe
Baymont by Wyndham Freeport

Baymont by Wyndham Freeport

2.5 out of 5
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is €82 per night from 21 Sept to 22 Sept
€82
21 Sept - 22 Sept
includes taxes & fees
8/10 Very Good! (679 reviews)
"Staff and service were great. Carpet and walls/trim on all floors were dirty and peeling. Overall a good stay."

Reviewed on 20 Aug 2025

Baymont by Wyndham Freeport
See all 98 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 €824 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.