5 Stars Hotels in Downtown Chicago, Chicago from CA $475

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Nov 14 - Nov 15
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Nov 20 - Nov 22
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Nov 27 - Nov 29

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, (999 reviews)
"Great place to stay in Chicago!"
United States
ryan
The price is CA $599
CA $713 total
includes taxes & fees
Dec 13 - Dec 14
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, (2,075 reviews)
"Amazing property and hospitality!"
United States
Matthew
The price is CA $562
CA $668 total
includes taxes & fees
Dec 14 - Dec 15
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, (1,000 reviews)
"Always an incredible hotel! Definitely one of the best in the USA"
United States
Vincent Haley
The price is CA $749
CA $891 total
includes taxes & fees
Dec 13 - Dec 14
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, (1,000 reviews)
"Amazing hotel, best location"
United States
Talia
The price is CA $621
CA $738 total
includes taxes & fees
Dec 13 - Dec 14
The Langham, 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, (1,000 reviews)
"Very clean and upscale property. Lovely amenities. Great location and staff very friendly."
United States
Loai
The price is CA $625
CA $743 total
includes taxes & fees
Dec 13 - Dec 14
Waldorf Astoria Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.

6. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,004 reviews)
"Very helpful staff good for families"
United States
Krikour
The price is CA $530
CA $630 total
includes taxes & fees
Dec 13 - Dec 14
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, (968 reviews)
"The wellness center was my favorite!"
United States
Mauro
The price is CA $475
CA $600 total
includes taxes & fees
Nov 22 - Nov 23
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.

8. 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 CA $606
CA $721 total
includes taxes & fees
Dec 13 - Dec 14
Park Hyatt 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, (136 reviews)
"Gorgeous and family friendly"
United States
Alise
The price is CA $803
CA $955 total
includes taxes & fees
Dec 3 - Dec 4
The St. Regis Chicago

Top Downtown Chicago Hotel Reviews

A cityscape with a river, a bridge, and a dining area with tables and chairs.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago

10/10 Excellent

This property is perfect. Truly a 5 star experience.
Canada
James
Reviewed October 21, 2026
Trump International Hotel & Tower Chicago

Find out more about Downtown Chicago

Five Star Hotels in Downtown Chicago

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Downtown Chicago so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Downtown Chicago and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Downtown Chicago

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Downtown Chicago

The results are in, and Downtown Chicago 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Downtown Chicago! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Downtown Chicago today and settle down in the lap of luxury tomorrow.

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 things such as when you plan to go and the length of your trip. A top tip for landing the best deal? Use our pricing filters to check out all of the available options for your chosen dates.

  • Search for the lowest price per night from CA $475

What makes a hotel 5 stars in Downtown Chicago?

In Downtown Chicago, a hotel needs to provide a specific amount of upscale features to be designated 5 stars. These can include gourmet restaurants, saunas and spas, on-site gyms, premium bedding, complimentary luxury toiletries and more. What also sets 5-star hotels apart is their extraordinary standard of service. You'll enjoy things like in-room massages, concierge services and nightly turn-down services. Some may even offer extra touches such as welcome gifts.

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

Our convenient filters are the quickest way to narrow down what you're looking for. Check the "All inclusive" and "5-star" boxes to show the finest resorts in Downtown Chicago where your room, meals, entertainment and activities are included in the price. At these retreats, your vacation is absolute indulgence from the moment you check in.

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 retreats that promise a fabulous getaway. Find one that matches your needs by searching our vacation rentals in Downtown Chicago.

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