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Five Star Hotels in Downtown Chicago

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Check availability on Downtown Chicago 5 Star Hotels

This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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, (1,001 reviews)
"The staff was so kind and helpful. Great location and dining options. The room was spotless and comfortable"
United States
Teresa
The price is S$805
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, (2,034 reviews)
"beautiful property in a great location highly recommend staying here this will be our go to spot when visiting chicago"
United States
Mark
The price is S$701
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, (1,000 reviews)
"Enjoyed my stay, lovely staff and great location"
United States
Saramae
The price is S$866
includes taxes & fees
25 Oct - 26 Oct
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 S$949
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, (1,002 reviews)
"Great hotel"
United States
Luis
The price is S$840
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, (941 reviews)
"Great location Helpful staff"
United States
Abhay
The price is S$700
includes taxes & fees
25 Oct - 26 Oct
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, (1,000 reviews)
"Nice clean hotel in a great location."
United States
Tom
The price is S$834
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, (1,000 reviews)
"Staff was excellent."
United States
Fred
The price is S$723
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, (132 reviews)
"The location is great. Lovely hotel with great staff."
United States
Xiomara
The price is S$951
includes taxes & fees
29 Oct - 30 Oct
The St. Regis Chicago
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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 Downtown Chicago.
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
The price is S$254 per night from 1 Nov to 2 Nov
S$254
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (5,460 reviews)
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Learn more about Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

See all hotels in Downtown Chicago
A cityscape with tall skyscrapers and a historic tower.

Top Downtown Chicago Hotel Reviews

Find out more about Downtown Chicago

Stay in Luxury: 5 Star Hotels in Downtown Chicago

There's nothing wrong with enjoying the finer things in life. Indulge your every desire on your upcoming leisure time. Treat yourself with a stay in a 5-star hotel during your Downtown Chicago trip. You'll join the multitudes of holidaymakers who have made Downtown Chicago so fashionable recently. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Downtown Chicago and indulge in the finer things in life for a while.

5-Star Hotels in Downtown Chicago

You'll have a wonderful time at one of these 5-star hotels. Exceptional customer care, luxurious bedding, and deeply relaxing spa offerings are waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A body scrub that will leave you feeling refreshed and alive? Butler services? Whatever it is your heart desires, you're bound to find it here. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs. 

But you aren't going to spend your entire holiday in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Downtown Chicago are waiting for you to relax after an exciting day.

Make Your Escape

The results are in, and Downtown Chicago 5-star hotels are the place to be when you book your next holiday. If you've been dreaming about a holiday set here, then go ahead and book it. It's time to plan your next great escape -- this is a great time to find 5-star hotel deals in Downtown Chicago! Choose one of our Downtown Chicago 5-star hotels today and soothe yourself in luxe surroundings at your convenience.


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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Downtown Chicago?
The amount you pay for a 5-star hotel in Downtown Chicago depends on factors like when you plan to travel and the length of your getaway. Our top tip for bagging an awesome deal? Use our pricing filters to check out the available accommodation for your selected dates.

  • Search for the lowest price per night from S$217

What makes a hotel 5 stars in Downtown Chicago?
In Downtown Chicago, a hotel must offer a certain number of high-end conveniences to earn a 5-star rating. These may include gourmet restaurants, saunas and spas, on-site gyms, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their exceptional service. You can look forward to things like nightly turn-down services, in-room massages and concierge services. Some may even offer thoughtful touches such as a welcome gift.
Are there any 5-star all-inclusive resorts in Downtown Chicago?
Our handy filters are the easiest way to find exactly what you want. Check the "All inclusive" and "5-star" boxes to see the most upscale resorts in Downtown Chicago where your meals, lodging, entertainment and activities are included in the price. At these stays, your trip is pure extravagance from the moment you pull up to the entrance.

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