Find 5 Star Hotels in Downtown Chicago, IL from SAR 1,336

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Check prices for these dates

Tonight
8 Nov - 9 Nov
Tomorrow
9 Nov - 10 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Our top choices for Downtown Chicago 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)
"Great place to stay in Chicago!"
United States
ryan
The price is SAR 1,877
SAR 2,231 total
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, (2,079 reviews)
"Amazing property and hospitality!"
United States
Matthew
The price is SAR 1,731
SAR 2,059 total
includes taxes & fees
15 Nov - 16 Nov
Trump International Hotel & Tower Chicago
A rooftop bar with seating and a view of the city skyline at night.

3. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,008 reviews)
"Always an incredible hotel! Definitely one of the best in the USA"
United States
Vincent Haley
The price is SAR 2,252
SAR 2,678 total
includes taxes & fees
6 Dec - 7 Dec
The Peninsula Chicago
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

4. The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,004 reviews)
"Attentive staff and beautiful spa, pool and rooms."
United States
Courtney
The price is SAR 1,959
SAR 2,330 total
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, (1,001 reviews)
"Great hotel"
United States
Luis
The price is SAR 1,675
SAR 1,992 total
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, (1,001 reviews)
"Very helpful staff good for families"
United States
Krikour
The price is SAR 1,675
SAR 1,992 total
includes taxes & fees
7 Dec - 8 Dec
The Ritz-Carlton, Chicago
A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.

7. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (965 reviews)
"Great location Helpful staff"
United States
Abhay
The price is SAR 1,337
SAR 1,683 total
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, (1,002 reviews)
"Excellent experience. I’d recommend this property for their outstanding service and updated rooms."
United States
Marissa
The price is SAR 1,643
SAR 1,954 total
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 SAR 2,012
SAR 2,392 total
includes taxes & fees
22 Nov - 23 Nov
The St. Regis Chicago

Top Downtown Chicago Hotel Reviews

A rooftop bar with seating and a view of the city skyline at night.
The Peninsula Chicago

The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago

10/10 Excellent

Excellent hotel, my only complaint would be the Peninsula food service. We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely wasn’t. The whole Peking duck was arranged haphazardly on the plate, the skin was not really crispy, and the taste experience was completely lackluster. As to the main dining room the service...
United States
Michael
Reviewed September 27, 2025
The Peninsula Chicago

Frequently Asked Questions

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

How much you pay for a 5-star hotel in Downtown Chicago depends on factors like when you want to go and the length of your break. A top tip for scoring an awesome deal? Use our pricing filters to check out the available accommodations for your chosen dates.

  • Search for the lowest price per night from SAR 1,336

What makes a hotel 5 stars in Downtown Chicago?

From high-end dining venues and fitness centers to swimming pools and premium bedding, the 5-star experience in Downtown Chicago is all about relaxation and luxury. But it takes more than just upscale amenities to get a 5-star rating. Hotels also have to deliver outstanding guest services like beauty treatments, on-site dry cleaning and laundry and 24-hour room service.

Are there any 5-star all-inclusive resorts in Downtown Chicago?

Use Expedia's filters to find a high-end retreat in Downtown Chicago where most of what you need is included. From there, narrow down your results for resorts that have 5 stars and are categorized as "All inclusive." The first thing to look forward to at these stays? Pure enjoyment and indulgence.

Are there any 5-star vacation rentals in Downtown Chicago?

Although you won't find any 5-star vacation rentals in Downtown Chicago on our site, we have a range of stays that promise a terrific getaway. Discover one that matches your style by checking out our vacation rentals in Downtown Chicago.