Find 5 Star Hotels in Sleepy Hollow, IL

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Check availability on Sleepy Hollow 5 Star Hotels

Tonight
31 Jan - 1 Feb
Tomorrow
1 Feb - 2 Feb
This weekend
31 Jan - 2 Feb
Next weekend
7 Feb - 9 Feb

Compare Sleepy Hollow 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

L7 Chicago by LOTTE
View from room

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (1563)
"meow"
The price is AED 584
AED 686 total
includes taxes & fees
2 Feb - 3 Feb
L7 Chicago by LOTTE
citizenM Chicago Downtown
Interior

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (2622)
"Best hotel stay ever!"
The price is AED 364
AED 427 total
includes taxes & fees
5 Feb - 6 Feb
citizenM Chicago Downtown
Hilton Chicago
Pool

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (1637)
"Beautiful room with an exceptional view of Lake Michigan!"
The price is AED 449
AED 635 total
includes taxes & fees
7 Feb - 8 Feb
Hilton Chicago
Congress Plaza Hotel
Exterior detail

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8465)
"The staff was wonderful and accommodating. I had high hopes that since i had booked the rooms several months in advanced that they would have been together, but I'm sure that is not something that can be helped. I had a wonderful stay and that is what mattered the most. "
The price is AED 341
AED 400 total
includes taxes & fees
1 Feb - 2 Feb
Congress Plaza Hotel
Eurostars Magnificent Mile
Room

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2843)
"Beautiful hotel, restaurant/bar when initially walking in. Bed was uncomfortable, that mattress probably needs to be replaced."
The price is AED 353
AED 414 total
includes taxes & fees
2 Feb - 3 Feb
Eurostars Magnificent Mile
Aloft Chicago Mag Mile
Exterior

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2560)
"N"
The price is AED 309
AED 362 total
includes taxes & fees
3 Feb - 4 Feb
Aloft Chicago Mag Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1796)
"Great"
The price is AED 350
AED 410 total
includes taxes & fees
9 Feb - 10 Feb
DoubleTree by Hilton Chicago - Magnificent Mile
Pendry Chicago
Exterior

Pendry Chicago

4.5 star property
9.4 out of 10, Exceptional, (1005)
"It was amazing, easy to get around with bus stops right next to it, and central."
The price is AED 606
AED 862 total
includes taxes & fees
16 Feb - 17 Feb
Pendry Chicago
Hyatt Regency Chicago
Exterior

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3183)
"I’ll stay here again!"
The price is AED 559
AED 764 total
includes taxes & fees
16 Feb - 17 Feb
Hyatt Regency Chicago
River Hotel
Front of property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3752)
"Good Location 😃"
The price is AED 275
AED 323 total
includes taxes & fees
24 Feb - 25 Feb
River Hotel
Palmer House a Hilton Hotel
Exterior

Palmer House a Hilton Hotel

4.0 star property
8.2 out of 10, Very Good, (1621)
"Limited bar/dining access. "
The price is AED 450
AED 620 total
includes taxes & fees
7 Feb - 8 Feb
Palmer House a Hilton Hotel
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (1401)
"Excelente opción de hotel. Muy buenas instalaciones, el staff super servicial. Yo fui de viaje con mi familia y niño y creo que fue la mejor opción. Super bien ubicado con varias alternativas de cafés , restaurantes cerca ."
The price is AED 364
AED 530 total
includes taxes & fees
2 Feb - 3 Feb
Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North
Exterior

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
8.4 out of 10, Very Good, (3550)
"Spacious and convenient! "
The price is AED 432
AED 507 total
includes taxes & fees
9 Feb - 10 Feb
Embassy Suites by Hilton Chicago Downtown River North
Freehand Chicago
Lobby lounge

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (1632)
"Everything "
The price is AED 227
AED 318 total
includes taxes & fees
12 Feb - 13 Feb
Freehand Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very Good, (2898)
"Checking in was good we got to check in a little early. Rooms were nice, beds comfortable, self service snack and drink open 24/7 was great. They had Tylenol and ibuprofen available as well as other essential needs. We used the gym and it had everything we needed for a quick workout. "
The price is AED 309
AED 362 total
includes taxes & fees
11 Feb - 12 Feb
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown Riverwalk
Property entrance

Hilton Garden Inn Chicago Downtown Riverwalk

3.0 star property
9.0 out of 10, Wonderful, (1915)
"Very friendly "
The price is AED 400
AED 470 total
includes taxes & fees
1 Feb - 2 Feb
Hilton Garden Inn Chicago Downtown Riverwalk
Hyatt Centric The Loop Chicago
Exterior

Hyatt Centric The Loop Chicago

4.0 star property
8.8 out of 10, Excellent, (1719)
"I don't stay in a lot of proper hotels so when I do, I'm always easily amazed. Hyatt Centric easily amazed me. A nice, shiny, squeaky-clean business-oriented hotel that made it easy to be comfortable. It was fun."
The price is AED 398
AED 467 total
includes taxes & fees
1 Feb - 2 Feb
Hyatt Centric The Loop Chicago
Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (1978)
"good location.....had a great Christmas"
The price is AED 403
AED 473 total
includes taxes & fees
16 Feb - 17 Feb
Hilton Chicago/Magnificent Mile Suites
Fairmont Chicago at Millennium Park
Exterior

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1623)
"Loved the lodge theme."
The price is AED 625
AED 841 total
includes taxes & fees
1 Feb - 2 Feb
Fairmont Chicago at Millennium Park
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.0 out of 10, Very Good, (1513)
"Check in and check out was fast and easy, the staff was great, and the hotel was overall great. "
The price is AED 287
AED 348 total
includes taxes & fees
3 Feb - 4 Feb
Hotel Saint Clair- Magnificent Mile
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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Sleepy Hollow?
The amount you pay for a 5-star hotel in Sleepy Hollow depends on things like when you plan to travel and the length of your escape. A top tip for bagging an awesome deal? Use our pricing filters to compare all of the available options for your selected dates.

  • Search for the lowest price per night

What makes a hotel 5 stars in Sleepy Hollow?
From fine dining venues and 24/7 fitness centers to pools and deluxe bedding, the 5-star experience in Sleepy Hollow is all about luxury and comfort. But it requires more than just top-notch amenities to receive a 5-star rating. Stays also have to provide extraordinary guest-centric services like beauty treatments, dry cleaning and laundry and 24-hour room service.
Are there any 5-star all-inclusive resorts in Sleepy Hollow?
Find an upscale stay that includes your lodging, meals, bar and entertainment in Sleepy Hollow with our filter tool. Search for hotels with a 5-star rating and select the “All inclusive” filter. Have a look at what’s included in the price. That way, you’re ready to take advantage of all the perks on offer from the moment you arrive.
Are there any 5-star vacation rentals in Sleepy Hollow?
There are no 5-star vacation rentals in Sleepy Hollow on our site, but there are some other highly rated options worth looking into. Scan through our vacation rentals in Sleepy Hollow to book the ideal place for your getaway.