
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.

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,796, price is now CA $1,339 per person
CA $1,339
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,784 reviews)
Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too.
Reviewed on Jun 3, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,329, price is now CA $1,672 per person
CA $1,672
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) 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

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $3,337, price is now CA $2,427 per person
CA $2,427
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great room, professional staff, no complaints.
Reviewed on May 31, 2026

The Emily Hotel
Downtown Chicago
Price was CA $2,167, price is now CA $1,609 per person
CA $1,609
per person
Aug 24 - Aug 28
found 19 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
Convenient location and easy building to deal with. Parking was a little expensive.
Reviewed on Jun 2, 2026

Thompson Chicago, by Hyatt
Downtown Chicago
Price was CA $1,996, price is now CA $1,489 per person
CA $1,489
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (1,370 reviews)
The hotel was very clean and a great location within Chicago close to restaurants and shopping.
Reviewed on Jun 2, 2026
Winslow Hotel Deals

Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
The price is CA $175 per night from Jul 2 to Jul 3
CA $175
CA $195 total
Jul 2 - Jul 3
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 $125 per night from Jun 28 to Jun 29
CA $125
CA $137 total
Jun 28 - Jun 29
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 $130 per night from Jun 22 to Jun 23
CA $130
CA $145 total
Jun 22 - Jun 23
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.







