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The Latest Winslow Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.4/10 Very Good! (3,506 reviews)
Close to Michigan Ave and lots of restaurants. Didn't like that the cleaning lady came at 5pm while we were trying to get ready for dinner. So we didn't get service. Asked the front desk for some coffee creamer to be sent to our room, never received. Beds not the most comfortable.
Reviewed on Jul 29, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
The hotel is in a fantastic location. Staff service was very high quality and the lobby and common areas were very clean and well organized. Gym was modern, big and clean.
The actual room had some marks on the walls and a buzzy air handling vent in the master. An automated lighting system that was a bit dim and difficult to use. We would stay again.
Mini bar and snacks were high quality. We would stay again.
Reviewed on Jul 29, 2025

Fairmont Chicago at Millennium Park
Downtown Chicago
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per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.6/10 Excellent! (1,795 reviews)
We recently stayed at the Fairmont Chicago Millennium Park in a Gold Level room for 2 nights and overall had a very good experience. The room was clean, well-sized, and the bed was very comfortable. Water pressure in the shower was excellent—something we definitely appreciate after a long day of walking around the city.
The Gold Level service was a highlight. The lounge was well maintained, and the Gold team did a fantastic job keeping the space clean, welcoming, and comfortable. Breakfast, evening canapés, and desserts were enjoyable, though the selection seemed more limited compared to other Fairmont properties we've stayed at.
One minor issue: there was no complimentary water in the room upon check-in, but once we called down, it was promptly delivered with no hassle. They had Evian water bottle and other minibar items available but it comes with extra cost.
The location is another strong point. It’s about a 10-minute walk to cross the river to Michigan Avenue, 15–20 minutes to Navy Pier, and just 10 minutes to Cloud Gate (The Bean). We didn’t have a car, so we can’t speak to the parking situation.
While it didn’t quite match the level of service and amenities we've come to expect from other Fairmont hotels, it was still a comfortable and pleasant stay overall.
Reviewed on Jul 28, 2025

Hilton Chicago
Downtown Chicago
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per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
Todo muy lindo , el personal muy atento, amable la comida exquisita la atención excelente cuando vuelva a Chicago me quedaré de nuevo hay 🙏
Reviewed on Jul 30, 2025

Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.8/10 Excellent! (3,033 reviews)
Lots of great dining options around the area. The breakfast at the hotel was great.
Reviewed on Jul 29, 2025
Find the Best Winslow Vacation Packages
Winslow Hotel Deals

AmericInn by Wyndham Monroe
424 4th Ave, Monroe, WI
Fully refundableReserve now, pay when you stay
The price is ₩172,346 per night from Aug 17 to Aug 18
₩172,346
₩188,719 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (355 reviews)
"The room still smelled and looked new. And staff very nice."
Reviewed on Jul 18, 2025

Super 8 by Wyndham Freeport
1551 Sleezer Home Rd, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is ₩113,971 per night from Aug 3 to Aug 4
₩113,971
₩126,480 total
Aug 3 - Aug 4
includes taxes & fees
6.8/10 (331 reviews)
nicer than I expected
"I didnt go in expecting a lot, but the hotel was way nicer than I thought. Always thought "super 8" was just a cheap place, some might be, but this one was nice"
Reviewed on Jul 17, 2025

Baymont by Wyndham Freeport
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is ₩133,499 per night from Aug 10 to Aug 11
₩133,499
₩148,157 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (671 reviews)
Good option in area
"Very nice Staff… Property a little rundown was the only reason I marked down one star. I would stay here again."
Reviewed on Jul 26, 2025
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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