Winslow Vacations from $557
Book a Hotel + Flight or Car together to unlock savings
Your Winslow Vacation
Memorable adventures await when you reserve a vacation package to Winslow. Whether you're a foodie, history buff or just a traveler who loves to discover new places, there's something for everyone in this awesome city. Any trip to Winslow has to include a little sightseeing. Lake Le Aqua Na State Park is a great place to begin exploring. Stop daydreaming and start traveling. Check out the range of options on Expedia today and put your Winslow vacation plans into motion!
The Latest Winslow Vacation Packages
- Level Chicago Fulton Market
Dec 24 - Dec 29Level Chicago Fulton Market + Flight
Downtown Chicago5 nights4.0 star property9.2/10 - Wonderful (604 reviews)"Weird space w the way the bed is no access off the side and the counter was stained badly. There was a 28$ additional amenity fee that they slapped on upon check in. The pool is closed and didn’t use the weight room it was a one night stay. over priced but could be ok for a long stay w the kitchen"Reviewed November 6, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$857$557found 1 day agoper traveler - Sheraton Grand Chicago Riverwalk
Dec 8 - Dec 13Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago5 nights4.0 star property8.6/10 - Excellent (1,878 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$1,720$622found 1 day agoper traveler - Hotel Riu Plaza Chicago
Dec 8 - Dec 13Hotel Riu Plaza Chicago + Flight
Downtown Chicago5 nights4.0 star property9.4/10 - Exceptional (5,651 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$1,008$630found 1 day agoper traveler - Park Hyatt Chicago
Dec 10 - Dec 13Park Hyatt Chicago + Flight
Downtown Chicago3 nights5.0 star property9.6/10 - Exceptional (1,001 reviews)"Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."Reviewed November 4, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$1,826$1,237found 1 day agoper traveler - LondonHouse Chicago, Curio Collection by Hilton
Dec 8 - Dec 13LondonHouse Chicago, Curio Collection by Hilton + Flight
Downtown Chicago5 nights4.5 star property9.4/10 - Exceptional (3,894 reviews)"The staff was excellent! The views were amazing and the rooms were clean. The rooftop restaurant/ bar 🎇"Reviewed November 7, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$1,135$774found 1 day agoper traveler
Winslow Hotel Deals
Country Inn & Suites by Radisson, Stockton, IL
Country Inn & Suites by Radisson, Stockton, IL"The weekend breakfast cooked to order is an interesting idea except when you’re not the first ones there. Fortunately there were other things to eat while we waited. Breakfast was pretty good except for the extremely salty sausages."
"Enjoyed the custom made omelet. Friendly staff. Hot tub was wonderful."
"Breakfast buffet was good"
City Express By Marriott Freeport
City Express By Marriott Freeport
"Very nice rooms, right by the town square. Definitely would stay again!"
"Property was fine"
Frequently Asked Questions
How much does a Winslow vacation package cost?
You'll find cheap prices from $557 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.