
Winslow Vacation Packages
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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!
Top Winslow Vacation Deals
Price found within the past 48 hours. Click for updated prices.


Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,708, price is now CA $1,084 per person
CA $1,084
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (488 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,858, price is now CA $1,231 per person
CA $1,231
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
The room itself was excellent — 9/10. The view was amazing, the bed was very comfortable, and the room was spacious and well-designed.
However, for the price and for a hotel that markets itself as a 4-star property, many amenities were disappointing.
First, the coffee machine in the room was very low quality, more comparable to what you would typically find at a Comfort Inn. There were also no bathrobes or hotel slippers provided, which I would expect at this price point.
The lobby was surprisingly small and not particularly inviting. It felt dark and lacked the atmosphere you would expect from a higher-end hotel.
The hotel only has one restaurant, and unfortunately the food quality was below average.
Another disappointment was the rooftop. The hotel advertises rooftop access, but the rooftop is not actually owned or operated by the hotel. During our stay, it was closed for a private event, making it unavailable to guests.
To make matters worse, on the day we checked out, the elevator was out of service, so we had to carry our luggage down the stairs ourselves.
Overall, I would rate the room 9/10, but the amenities, dining, and overall hotel experience only 2/10.
Because the room and view were truly outstanding, I would give the hotel an overall rating of 7/10. Without the exceptional room and view, my rating would have been significantly lower.
Reviewed on Jun 2, 2026


Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,535, price is now CA $1,079 per person
CA $1,079
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,732 reviews)
The hotel location and room was nice. I didn’t like that you had to pay $5 per bag for storage if you wanted to check out if the room early. I thought giving the room before noon would be better for them especially since I was coming back before that checkout time. So I just brought my stuff back up to the room
Other than that the front desk and cleaning ladies was very nice.
Reviewed on May 29, 2026
Winslow Hotel Deals

Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is CA $178 per night from Jun 21 to Jun 22
CA $178
CA $197 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (899 reviews)
"The hotel and propert clean. Room nice. Just wish there was shower curtain on shower pole. Everything else was nice. We had handicap room. 235."
Reviewed on Jun 1, 2026

Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Jun 9 to Jun 10
CA $122
CA $134 total
Jun 9 - Jun 10
includes taxes & fees
9/10 Wonderful! (863 reviews)
"Very good place to come back and relax had a good breakfast and cool and hot tub are very relaxing"
Reviewed on Jun 1, 2026

Country Inn & Suites by Radisson, Stockton, IL
200 Dillon Ave Stockton IL
The price is CA $128 per night from Jul 1 to Jul 2
CA $128
CA $142 total
Jul 1 - Jul 2
includes taxes & fees
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







