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Sleepy Hollow Hotel Guide - 5 Stars Hotels in Sleepy Hollow, Chicago

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Our top choices for Sleepy Hollow 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,002 reviews)
"Was amazing experience we want to go back"
United States
Edda
The price is Rp9.307.480
Rp11.065.662 total
includes taxes & fees
1 Nov - 2 Nov
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (2,047 reviews)
"clean room, friendly staff, great restaurants, good location"
United States
Cecille
The price is Rp8.255.914
Rp9.815.454 total
includes taxes & fees
1 Nov - 2 Nov
Trump International Hotel & Tower Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.

3. The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,001 reviews)
"Enjoyed my stay, lovely staff and great location"
United States
Saramae
The price is Rp9.593.864
Rp11.406.146 total
includes taxes & fees
1 Nov - 2 Nov
The Langham, Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.

4. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,000 reviews)
"This place was everything!! The location, comfort, food and the stamp was top tier!!!"
United States
Levi
The price is Rp11.634.350
Rp13.832.168 total
includes taxes & fees
1 Nov - 2 Nov
The Peninsula Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,000 reviews)
"Great hotel"
United States
Luis
The price is Rp9.660.985
Rp11.485.945 total
includes taxes & fees
1 Nov - 2 Nov
Waldorf Astoria Chicago
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (946 reviews)
"Great location Helpful staff"
United States
Abhay
The price is Rp8.291.712
Rp10.305.490 total
includes taxes & fees
2 Nov - 3 Nov
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.

7. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,005 reviews)
"Nice clean hotel in a great location."
United States
Tom
The price is Rp9.794.333
Rp11.644.482 total
includes taxes & fees
1 Nov - 2 Nov
Park Hyatt Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.

8. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
"Staff was excellent."
United States
Fred
The price is Rp9.052.419
Rp10.762.420 total
includes taxes & fees
1 Nov - 2 Nov
The Ritz-Carlton, Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.

9. The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (134 reviews)
"The location is great. Lovely hotel with great staff."
United States
Xiomara
The price is Rp10.399.319
Rp12.363.750 total
includes taxes & fees
8 Nov - 9 Nov
The St. Regis Chicago
A rooftop lounge with a city skyline view, featuring a sofa set with patterned cushions and a table with drinks and snacks.

10. Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2 reviews)
Art Villa
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Sleepy Hollow.
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
The price is Rp2.723.333 per night from 25 Oct to 26 Oct
Rp2.723.333
Rp3.237.750 total
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (5,513 reviews)
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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Sleepy Hollow?
How much you pay for a 5-star hotel in Sleepy Hollow depends on factors like when you plan to go and the length of your getaway. Our insider tip for landing an awesome deal? Use our pricing filters to check out all of the available accommodation for your preferred dates.

  • Search for the lowest price per night from Rp3.042.418

What makes a hotel 5 stars in Sleepy Hollow?
Exemplary guest service characterises every 5-star hotel in Sleepy Hollow. From the moment you enter the lobby, staff cater to your every need, whether offering luggage assistance and storage or providing a nightly turn-down service. On top of that, hotels must offer upscale conveniences to be considered for a 5-star rating. These can include luxury bath products, an on-site spa, swimming pools, fine dining restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Sleepy Hollow?
Our filter tool is the best way to narrow down what you want. Select "5-star" and "All inclusive" to see the most luxurious hotels in Sleepy Hollow where your meals, lodging, activities and entertainment are included in the price. At these escapes, your holiday is pure extravagance from the moment you arrive.