Winslow Vacations from NT$43,673
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- Plan, book, travel with confidence
- Better togetherSave up to NT$25,000 when you book a flight and hotel together*
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The Latest Winslow Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
NT$57,469
per person
Sep 26 - Sep 30
found 18 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The service and rooms were excellent. Beds were comfortable and views were to die for. The food at Terra16 was a good but the wait times and food service took to long. Our fruit platter took over a half hour for breakfast. The spa was nice, but the lockers were hard to use or some worked and some did not lock. Front desk was exceptional and property was gorgeous. I would definitely stay again and was very happy with the staff who generally were attentive and kind.
Reviewed on 2026/8/13
Find the Best Winslow Vacation Packages
Winslow Hotel Deals
City Express By Marriott Freeport
1060 Riverside Dr Freeport IL
Fully refundableReserve now, pay when you stay
NT$3,164
NT$3,511 total
Aug 25 - Aug 26
includes taxes & fees
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
NT$3,540
NT$3,929 total
Aug 23 - Aug 24
includes taxes & fees
9/10 Wonderful! (926 reviews)
"The breakfast was the highlight. Waffle bar, cereal, oatmeal, muffins, fruit, eggs, bacon or sausage, biscuits/gravy, and bagels."
Reviewed on 2026/8/8
Country Inn & Suites by Radisson, Stockton, IL
200 Dillon Ave Stockton IL
NT$2,492
NT$2,766 total
Sep 3 - Sep 4
includes taxes & fees
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 vacation package cost?
You'll find cheap prices from NT$43,673 on Expedia for your Winslow escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation 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 vacation packages and you could land some excellent off-season deals.
How many days is enough for Winslow?
With a well-organized 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 vacation 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 vacation package as early as possible.
Is it cheaper to book a Winslow vacation as a package?
You can enjoy significant savings on your next Winslow retreat by booking a tailored vacation 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 vacation 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 accommodations and airfare: Once you've nailed down your travel dates and duration, book the right Winslow vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
