Winslow Vacations from $311
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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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $579, price is now $311 per person
$311
per person
Mar 27 - Mar 30
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!
Reviewed on Jan 11, 2026
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $598, price is now $339 per person
$339
per person
Mar 27 - Mar 30
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
room was clean, comfortable, & staff were kind and welcoming
Reviewed on Jan 12, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $611, price is now $366 per person
$366
per person
Mar 27 - Mar 30
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!
Reviewed on Jan 10, 2026
Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
Save 100% on your flight
Price was $564, price is now $348 per person
$348
per person
Apr 3 - Apr 8
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
I was greeted with a smile we checking our room and we were late. They were very accommodating. They have a bar which we went over to eat from. I don’t know the bartender’s real name we were cold to call her TT. She was the very best ever very kind very sociable and friendly. I will be returning to this property the next time I’m in Chicago. I really had a great experience at this hotel with the staff is also includes the manager the hotel clerk, as well as the security guard. I will give my experience at this hotel five stars.
Reviewed on Jan 12, 2026
Winslow Hotel Deals
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
$105 nightly
The price is $117 total per night from Feb 6 to Feb 7
$117 total
Feb 6 - Feb 7
Total with taxes and fees
8.8/10 Excellent! (856 reviews)
good deal
Reviewed on Jan 12, 2026
Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $80 total per night from Jan 26 to Jan 27
$80 total
Jan 26 - Jan 27
Total with taxes and fees
8.8/10 Excellent! (828 reviews)
Love this hotel, have stayed at it 3 times. You even get a discount at vinces just for staying at this hotel which is so kind of them
Reviewed on Jan 7, 2026
Baymont by Wyndham Freeport
1060 Riverside Dr Freeport IL
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Jan 20 to Jan 21
$85 total
Jan 20 - Jan 21
Total with taxes and fees
7.8/10 Good! (714 reviews)
Front desk staff was awesome, very professional, courteous and friendly, room was very clean bed was very comfortable
Reviewed on Jan 1, 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
