Winslow Vacations from $175

Book a Hotel + Flight or Car together to unlock savings

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.
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $312, price is now $175 per person
$175
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18/10 Exceptional! (1,001 reviews)
Best location to stay

Reviewed on Oct 25, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,139, price is now $473 per person
$473
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
17.6/10 Exceptional! (1,074 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.

Reviewed on Nov 17, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $493, price is now $263 per person
$263
per person
Jan 23 - Jan 26
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on Nov 9, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $349, price is now $189 per person
$189
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on Oct 28, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $318, price is now $181 per person
$181
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Staff was our favorite part! Very very professional and friendly

Reviewed on Nov 14, 2025

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Winslow Hotel Deals

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
$116 nightly
The price is $129 total per night from Nov 25 to Nov 26
$129 total
Nov 25 - Nov 26
Total with taxes and fees
8.8/10 Excellent! (842 reviews)
Great staff.

Reviewed on Nov 13, 2025

Country Inn & Suites by Radisson, Freeport, IL
Country Inn & Suites by Radisson, Stockton, IL

Country Inn & Suites by Radisson, Stockton, IL

2.5 out of 5
200 Dillon Ave Stockton IL
$83 nightly
The price is $92 total per night from Nov 30 to Dec 1
$92 total
Nov 30 - Dec 1
Total with taxes and fees
8.4/10 Very Good! (634 reviews)
Great service. Came early and room was ready

Reviewed on Nov 2, 2025

Country Inn & Suites by Radisson, Stockton, IL
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
$87 nightly
The price is $96 total per night from Dec 16 to Dec 17
$96 total
Dec 16 - Dec 17
Total with taxes and fees
7.8/10 Good! (705 reviews)
Had i not made my reservation ahead of time and saw the condition of the carpets first, I probably would have not checked in. If our room wasn't clean when we opened the room door, i would have left. It appears the hall/stair carpets have never been cleaned and/or vacuumed rarely. My first impression ...

Reviewed on Nov 1, 2025

Baymont by Wyndham Freeport
See all 102 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.

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 $175 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.