Winslow Vacations from $204

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Staybridge Suites, Lincolnshire by IHG

Staybridge Suites, Lincolnshire by IHG

3 out of 5
Half Day
Save 100% on your flight
Price was $348, price is now $204 per person
$204
per person
Jan 29 - Feb 2
found 18 hours ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
18/10 Exceptional! (1,000 reviews)
Everything was good

Reviewed on Nov 18, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,177, price is now $516 per person
$516
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
Great location and staff was very accommodating. Rooms were on the small side.

Reviewed on Nov 19, 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 $736, price is now $431 per person
$431
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,003 reviews)
Great location and room for the price. Restaurant downstairs is also very nice if you wanted to grab a meal without leaving. Only a few hundred yards from Blue Line stop which goes right to the airport, and the welcome drink was a nice touch. Staff was also super friendly and accommodating.

Reviewed on Nov 10, 2025

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $455, price is now $273 per person
$273
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
17.6/10 Exceptional! (1,079 reviews)
We Truly Enjoyed our stay. staff was Great . Helpful and Pleasant. Highly recommend staying here.

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 $1,522, price is now $918 per person
$918
per person
Dec 28 - Jan 2
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on Nov 9, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winslow
View all trips

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
$113 nightly
The price is $126 total per night from Nov 23 to Nov 24
$126 total
Nov 23 - Nov 24
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
$72 nightly
The price is $79 total per night from Nov 30 to Dec 1
$79 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
$88 nightly
The price is $98 total per night from Dec 4 to Dec 5
$98 total
Dec 4 - Dec 5
Total with taxes and fees
7.8/10 Good! (706 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winslow vacation package cost?
You'll find cheap prices from $204 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.