Compare and book 5 Star hotels in Sleepy Hollow, Chicago

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Check availability on Sleepy Hollow 5 Star Hotels

Tonight
1 Dec - 2 Dec
Tomorrow
2 Dec - 3 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Sleepy Hollow 5 Star Hotels

Reception
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1005)
"Amazing hotel"
United States
David
The price is 11.073.300 ₫
12.998.949 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Four Seasons Hotel Chicago
Lobby
The Langham, Chicago

The Langham, Chicago

5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1009)
"Spa ,pool are awesome "
United States
jared
The price is 12.042.214 ₫
14.136.355 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Langham, Chicago
Front of property – evening/night
The Peninsula Chicago

The Peninsula Chicago

5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1020)
"Great rooms, location and top flight service"
United States
Andrew
The price is 12.523.375 ₫
14.701.189 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
The Peninsula Chicago
Bar (on property)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1792)
"Great stay "
United States
Mohammed
The price is 9.135.472 ₫
10.724.128 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Trump International Hotel & Tower Chicago
Exterior
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1008)
"The staff was amazing. Will be making a return stay."
United States
Patricia
The price is 10.018.700 ₫
11.760.952 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Waldorf Astoria Chicago
Suite, Terrace (Water Tower) | Premium bedding, down duvets, pillow-top beds, minibar
Park Hyatt Chicago

Park Hyatt Chicago

5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1002)
"Stay was amazing!!! The staff was so friendly, kind, and thoughtful! The rooms were soooo beyond perfect and lovely! And the food at the restaurant was amazing.. especially breakfast! You won’t regret staying here!!! "
United States
Larissa
The price is 11.706.060 ₫
13.741.702 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Park Hyatt Chicago
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers
Nobu Hotel Chicago

Nobu Hotel Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (753)
"Great location, amenities and staff. "
United States
Nicholas
The price is 6.597.841 ₫
7.745.206 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Nobu Hotel Chicago
Bar (on property)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1005)
"Great breakfast a la carte menu, perfect bar setting, room was spotless, and service in accordance to the Ritz Brand."
United States
Alejandro Randolph
The price is 10.179.527 ₫
11.949.746 ₫ total
includes taxes & fees
30 Dec - 31 Dec
The Ritz-Carlton, Chicago
2 restaurants, breakfast served
The St. Regis Chicago

The St. Regis Chicago

5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (83)
"Nice place "
United States
John
The price is 11.758.790 ₫
13.803.643 ₫ total
includes taxes & fees
17 Dec - 18 Dec
The St. Regis Chicago
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
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.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL
The price is 2.425.580 ₫ per night from 7 Dec to 8 Dec
2.425.580 ₫
2.847.388 ₫ total
7 Dec - 8 Dec
includes taxes & fees
8.4/10 Very Good! (5,331 reviews)
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Top Sleepy Hollow Hotel Reviews

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 2.847.388 ₫

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.

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