Winslow Vacations from $600
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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.
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $899, price is now $600 per person
$600
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
The staff was very friendly and the location was great!
Reviewed on Jul 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,078, price is now $677 per person
$677
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
The male receptionist was extremely helpful, friendly, and welcoming. Unfortunately, the female receptionist was not as helpful or friendly. Her coworker noticed that I wasn't receiving the assistance I needed and stepped in to help, which I really appreciated.
I've stayed at several RIU hotels before and have always been able to check in early when a room was available. This was the first time I've experienced a significant delay with check-in.
Overall, I had a great stay. The hotel is in an excellent location, with everything within walking distance, making it very convenient to explore the area.
Breakfast is included, which is a nice benefit, but the quality could be improved. The selection was very basic and limited compared to what I've experienced at other RIU hotels.
Reviewed on Jul 2, 2026
Lodge Geneva National
Save 100% on your flight
Price was $1,083, price is now $696 per person
$696
per person
Sep 25 - Sep 29
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,375 reviews)
The Lodge is still under renovations. Our room was missing things like a headboard and bedside tables. The water pressure was weak. The amenities were nice for a family stay. It might be great once it’s all done. I wish we knew before booking.
Reviewed on Jun 27, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,461, price is now $1,616 per person
$1,616
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
This was our first stay at a Four Seasons — if there was 6 stars for the staff, I'd give it. Upon arrival, we were running late and trying to make an event. The Bellman immediately said he'd arrange transportation for us after we quickly went to the restrooms. We come back down to discover that he was going to drive us in the hotel's car —amazing service! And that's how the entire stay went. Amazing service, clean everything, amenities beyond expectations — it was a splurge, but a well worth one and we'll be back again!
Reviewed on Jul 2, 2026
Winslow Hotel Deals
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
$117 nightly
The price is $130 total per night from Jul 5 to Jul 6
$130 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (909 reviews)
"The room was amazing and clean. The staff was great and very accommodating. Breakfast was good and a great start to our day. Thet have a swimming pool and jacuzzi and it was very clean. We plan to come back again."
Reviewed on Jun 28, 2026
Country Inn & Suites by Radisson, Stockton, IL
200 Dillon Ave Stockton IL
$83 nightly
The price is $92 total per night from Aug 2 to Aug 3
$92 total
Aug 2 - Aug 3
Total with taxes and fees
8.4/10 Very Good! (679 reviews)
"The location is great and parking is easy. Lobby was clean and front desk staff very friendly. There was a roped off area in front of the main entrance door and the elevator was broken. The room has been updated, but isn't the cleanest. The main hall carpet is really run down. Our toilet srst was ..."
Reviewed on Jun 27, 2026
Super 8 by Wyndham Freeport
1551 Sleezer Home Rd Freeport IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $99 total per night from Aug 2 to Aug 3
$99 total
Aug 2 - Aug 3
Total with taxes and fees
7/10 Good! (371 reviews)
"When I checked in, we went to our room and received a text asking if we needed anything, I texted and stated we had no fridge or towels or wash cloths and stated I am a diabetic and I have to store my insulin in the fridge.i never received a response. My husband then called down to the desk after ..."
Reviewed on Jun 16, 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.
