Winslow Vacations from $389
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Your Winslow Vacation
Memorable adventures await when you reserve a vacation package to Winslow. Whether you're a foodie, history buff or just a traveler 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 traveling. Check out the range of options on Expedia today and put your Winslow vacation plans into motion!
The Latest Winslow vacation packages
Price found within the past 48 hours. Click for updated prices.
Chicago Lake Shore Hotel
Kenwood
$389
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7/10 Good! (1,004 reviews)
My stay at the Chicago Lake Shore Hotel was good! The outside of the facility looks to be in rough shape but once you step inside the rooms they are updated and very clean!!! I would stay here again for the price. Of they could update/renovate the outside this place would be 10/10!!!
Reviewed on Sep 22, 2026
Level Chicago – Old Town
Downtown Chicago
$656
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!
Reviewed on Sep 19, 2026
Stay One Chicago
Downtown Chicago
$1,088
per person
Nov 26 - Dec 1
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.8/10 Good! (12 reviews)
Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!
Reviewed on Sep 20, 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
$816
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,381 reviews)
Clean rooms, great convenient location in the loop. Staff was friendly and helpful. Would stay here again.
Reviewed on Sep 22, 2026
Kinzie Hotel
Downtown Chicago
$543
per person
Nov 26 - Dec 1
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,169 reviews)
The location of the hotel is perfect with easy access to most attractions. The staff was very nice. The room was clean. The facility is a little run down and we did wonder why every time we turn on the light on the bathroom there was a loud noise , it turns out that it was the fan and they do have a sign to notify guests including a night light so you don't have to turn the light on if you are just going in and out. The cocktail reception every day is a plus. I would stay again.
Reviewed on Sep 22, 2026
Winslow Hotel Deals
City Express By Marriott Freeport
1060 Riverside Dr Freeport IL
Fully refundableReserve now, pay when you stay
$107 nightly
$119 total
Sep 29 - Sep 30
Total with taxes and 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 Sep 22, 2026
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundableReserve now, pay when you stay
$109 nightly
$121 total
Oct 18 - Oct 19
Total with taxes and fees
9/10 Wonderful! (947 reviews)
"Good breakfast!"
Reviewed on Sep 22, 2026
Eugene Hotel
1517 11th St Monroe WI
Fully refundableReserve now, pay when you stay
$127 nightly
$139 total
Sep 24 - Sep 25
Total with taxes and 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 Sep 21, 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.
Find the Best Winslow Vacation Packages
Winslow Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Lake Le Aqua Na State Park, Famous Fossil Winery and Stagecoach Golf Course |
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Frequently asked questions
How much does a Winslow vacation package cost?
You'll find cheap prices from $389 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're likely to find lower prices and greater availability in December, January and February. Explore our cheap Winslow vacation packages and you could score some excellent off-season deals.
How many days is enough for Winslow?
With a well-planned schedule, you can easily hit the main Winslow attractions in a few days. But if you want to explore 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.
Does Expedia offer Book Now, Pay Later Winslow vacation packages?
Your Winslow trip is meant to be an escape from your busy life, not a reason for money worries. So to allow you that extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
