Compare and book 5 Star hotels in Sleepy Hollow, Chicago

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Check availability on Sleepy Hollow 5 Star Hotels

Top Sleepy Hollow 5 Star Hotels

Trump International Hotel & Tower Chicago
Bar (on property)

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1694)
"Location, staff and accommodations were excellent. "
The price is 12.117.960 ₫
14.225.274 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Trump International Hotel & Tower Chicago
Four Seasons Hotel Chicago
Reception

Four Seasons Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (1001)
"Great location "
The price is 13.924.160 ₫
16.345.571 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Four Seasons Hotel Chicago
The Langham, Chicago
Lobby

The Langham, Chicago

5.0 star property
9.8 out of 10, Exceptional, (1003)
"Location can’t be beat. Hotel is excellent! "
The price is 14.285.400 ₫
16.769.632 ₫ total
includes taxes & fees
7 Sept - 8 Sept
The Langham, Chicago
The Peninsula Chicago
Front of property – evening/night

The Peninsula Chicago

5.0 star property
9.8 out of 10, Exceptional, (1001)
"My favorite hotel"
The price is 16.420.000 ₫
19.275.438 ₫ total
includes taxes & fees
24 Aug - 25 Aug
The Peninsula Chicago
Waldorf Astoria Chicago
Exterior

Waldorf Astoria Chicago

5.0 star property
9.4 out of 10, Exceptional, (1001)
"Great location "
The price is 14.247.306 ₫
16.724.913 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Waldorf Astoria Chicago
Nobu Hotel Chicago
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers

Nobu Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (708)
"Beautiful, staffed with great people."
The price is 7.343.024 ₫
8.619.974 ₫ total
includes taxes & fees
24 Aug - 25 Aug
Nobu Hotel Chicago
Park Hyatt Chicago
Suite, Terrace (Water Tower) | 1 bedroom, premium bedding, down duvets, pillow-top beds

Park Hyatt Chicago

5.0 star property
9.6 out of 10, Exceptional, (1000)
"It's a beautiful and comfortable hotel."
The price is 16.157.280 ₫
18.967.032 ₫ total
includes taxes & fees
21 Aug - 22 Aug
Park Hyatt Chicago
The Ritz-Carlton, Chicago
Bar (on property)

The Ritz-Carlton, Chicago

5.0 star property
9.2 out of 10, Wonderful, (1001)
"Beautiful place "
The price is 15.106.400 ₫
17.733.863 ₫ total
includes taxes & fees
1 Sept - 2 Sept
The Ritz-Carlton, Chicago
The St. Regis Chicago
2 restaurants, breakfast served

The St. Regis Chicago

5.0 star property
9.0 out of 10, Wonderful, (72)
"Amazing hotel"
The price is 15.027.584 ₫
17.640.881 ₫ total
includes taxes & fees
2 Sept - 3 Sept
The St. Regis Chicago
Art Villa
Rooftop terrace

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is 11.455.906 ₫
21.916.341 ₫ total
includes taxes & fees
14 Sept - 15 Sept
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.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago, IL
The price is 4.555.565 ₫ per night from 4 Sept to 5 Sept
4.555.565 ₫
6.004.577 ₫ total
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (1,852 reviews)
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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.

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 4.232.419 ₫

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.