Compare and book 5 Star hotels in Countryside, Illinois

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Check prices for these dates

Tonight
5 Nov - 6 Nov
Tomorrow
6 Nov - 7 Nov
This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Countryside 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, (999 reviews)
"Great place to stay in Chicago!"
United States
ryan
The price is £432
includes taxes & fees
6 Dec - 7 Dec
Four Seasons Hotel Chicago
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (2,076 reviews)
"Amazing property and hospitality!"
United States
Matthew
The price is £407
includes taxes & fees
22 Nov - 23 Nov
Trump International Hotel & Tower Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.

3. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,007 reviews)
"Always an incredible hotel! Definitely one of the best in the USA"
United States
Vincent Haley
The price is £531
includes taxes & fees
6 Dec - 7 Dec
The Peninsula Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.

4. The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,004 reviews)
"Very well located and the service at this hotel was truly 5 stars The high tea was exceptional as well"
United States
Ana
The price is £462
includes taxes & fees
6 Dec - 7 Dec
The Langham, Chicago
A hotel entrance with a fountain, a car, and a person standing by the entrance.

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 £395
includes taxes & fees
6 Dec - 7 Dec
Waldorf Astoria Chicago
A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.

6. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,000 reviews)
"Very helpful staff good for families"
United States
Krikour
The price is £348
includes taxes & fees
6 Dec - 7 Dec
The Ritz-Carlton, Chicago
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.

7. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (962 reviews)
"Great location Helpful staff"
United States
Abhay
The price is £325
includes taxes & fees
22 Nov - 23 Nov
Nobu Hotel Chicago
A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.

8. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,001 reviews)
"Nice clean hotel in a great location."
United States
Tom
The price is £386
includes taxes & fees
22 Nov - 23 Nov
Park Hyatt Chicago
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.

9. The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (136 reviews)
"Gorgeous and family friendly"
United States
Alise
The price is £473
includes taxes & fees
22 Nov - 23 Nov
The St. Regis Chicago
A rooftop dining area with checkered tablecloths, red and blue plates, and a city skyline in the background.

10. Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2 reviews)
Art Villa

Top Countryside Hotel Reviews

A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
The Peninsula Chicago

The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago

10/10 Excellent

One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived. Outstanding!!
United Kingdom
Murray
Reviewed December 15, 2025
The Peninsula Chicago

Frequently Asked Questions

How much does it cost to stay in a 5-star hotel in Countryside?

The amount you pay for a 5-star hotel in Countryside can vary depending on when you want to travel and how long you plan to stay, among a range of factors. Use our price per night filter and other search tools to score the best rate on a luxurious stay.

  • Search for the lowest price per night from £325

What makes a hotel 5 stars in Countryside?

Exceptional guest service characterises every 5-star hotel in Countryside. From the instant you arrive, staff ensure your every need is met, whether recommending activities and tours or providing a nightly turn-down service. Plus, hotels have to offer upscale conveniences to be eligible for a 5-star rating. These can include luxury toiletries, an on-site spa, pools, fine dining kitchens and knowledgeable concierge.

Are there any 5-star all-inclusive resorts in Countryside?

Find a luxurious stay that includes your lodging, meals, drinks and entertainment in Countryside with the help of our filter tool. Search for properties rated 5 stars and select the "All inclusive" filter. Be sure to check what's included in the price. That way, you're ready to take advantage of all the premium perks when you get there.

Are there any 5-star holiday rentals in Countryside?

Our site doesn't have any 5-star holiday rentals in Countryside. However, you will still find some top-rated options where the only thing on your itinerary will be to relax and enjoy yourself. See what's available by searching through our holiday rentals in Countryside.

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