
Winslow Vacations from $576
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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 Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $950, price is now $576 per person
$576
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The property looks beautiful and the staff is very friendly. The details are, however, very lacking. The window in my room was drafty and upon inspection there were stains on the curtains. The shower had basically no edge to it and the curtain was short enough that the floor flooded when we showered. The bed was also not comfortable- especially the pillows which had zero support. It's a good location but I definitely won't be staying here again.
Reviewed on Mar 19, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,294, price is now $686 per person
$686
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The property is located within a short walk to the Magnificent Mile, restaurants, the north side of the river, Target, AMC theaters, Walgreens, Northwestern Medicine and the bus line. They have figured out convenience. The property was as beautiful as it was immaculate. The rooms were spacious with a fantastic shower and amazing shampoo, conditioner and lotion! I’ve even looked into buying it for my home. The breakfast buffet was unbelievable! The food was plentiful with more options than I thought possible. Even more impressive was the breakfast staff who kept the tables clean and the food available, hot and fresh. The hosts took a special interest in knowing the guests, and I know this first hand. My birthday fell during our stay, and the breakfast staff had a table waiting for my family and presented a birthday brownie with the words “Happy Birthday” written in chocolate sauce! Unfortunately, I had unexpectedly been hospitalized for emergency surgery so I missed the opportunity to experience their grand gesture, but the first morning I walked into breakfast after being discharged from the hospital, the host having never see me, asked if my family had given me the brownie. l was blown away! Will I stay again? Without any hesitation!!! Excellent choice!!
Reviewed on Mar 22, 2026

Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,178, price is now $735 per person
$735
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Clean room nice staff, beautiful property. Enjoyed the deluxe room
Reviewed on Mar 20, 2026

Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $2,703, price is now $1,737 per person
$1,737
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Exceptional hotel in the best location!
Reviewed on Mar 17, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,708, price is now $1,177 per person
$1,177
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
We only stayed for 1 night but the room was exceptionally clean, smelled fresh, and we had an amazing view! Would highly recommend
Reviewed on Mar 22, 2026
Winslow Hotel Deals

Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
$108 nightly
The price is $119 total per night from Apr 5 to Apr 6
$119 total
Apr 5 - Apr 6
Total with taxes and fees
9/10 Wonderful! (871 reviews)
Great breakfast
Reviewed on Mar 21, 2026

Hampton Inn Freeport
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Mar 29 to Mar 30
$108 total
Mar 29 - Mar 30
Total with taxes and fees
8.8/10 Excellent! (459 reviews)
Nice rooms. Good breakfast.
Reviewed on Mar 10, 2026

Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $77 total per night from Apr 5 to Apr 6
$77 total
Apr 5 - Apr 6
Total with taxes and fees
9/10 Wonderful! (838 reviews)
We stay here about once a year. The staff was nice. Room was clean Breakfast used to be good. It just was okay.
Reviewed on Mar 20, 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.



















