5 Stars Hotels in Drexel Estate, Chicago from CA $503

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Check prices for these dates

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Nov 7 - Nov 8
Tomorrow
Nov 8 - Nov 9
Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22

Our top choices for Drexel Estate 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 CA $706
CA $840 total
includes taxes & fees
Dec 6 - Dec 7
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, (2,077 reviews)
"Amazing property and hospitality!"
United States
Matthew
The price is CA $652
CA $775 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $848
CA $1,008 total
includes taxes & fees
Dec 6 - Dec 7
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 CA $737
CA $877 total
includes taxes & fees
Dec 6 - Dec 7
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 CA $630
CA $750 total
includes taxes & fees
Dec 6 - Dec 7
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 CA $630
CA $750 total
includes taxes & fees
Dec 7 - Dec 8
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 CA $503
CA $634 total
includes taxes & fees
Nov 22 - Nov 23
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 CA $618
CA $735 total
includes taxes & fees
Nov 22 - Nov 23
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 CA $757
CA $900 total
includes taxes & fees
Nov 22 - Nov 23
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 Drexel Estate Hotel Reviews

A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.
Nobu Hotel Chicago

Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago

10/10 Excellent

incredible staff and stay here. The team here crushed it and the rooms were fantastic
Canada
Jordan
Reviewed August 12, 2026
Nobu Hotel Chicago

Find out more about Drexel Estate

Five Star Hotels in Drexel Estate

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 Drexel Estate 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 Drexel Estate and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Drexel Estate

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 Drexel Estate

The results are in, and Drexel Estate 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 Drexel Estate! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Drexel Estate today and settle down in the lap of luxury tomorrow.

Frequently Asked Questions

What are the best 5-star hotels in Drexel Estate?

Based on Expedia traveller reviews, Nobu Hotel Chicago, The Langham, Chicago and Trump International Hotel & Tower Chicago are some of the most popular 5-star hotels in Drexel Estate. Featuring top-of-the-line amenities and unparalleled service, you can expect a luxurious and memorable stay.

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

How much you pay for a 5-star hotel in Drexel Estate depends on factors like when you plan to travel and the length of your trip. Our top tip for scoring an awesome 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 $503

What makes a hotel 5 stars in Drexel Estate?

In Drexel Estate, a hotel must provide a certain amount of upscale amenities to earn 5 stars. These can include gourmet restaurants, saunas and spas, on-site gyms, premium bedding, 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, nightly turn-down services and concierge services. Some may even offer additional touches like welcome gifts.

Are there any 5-star all-inclusive resorts in Drexel Estate?

Use our filters to find a high-end retreat in Drexel Estate where most of what you need is included in the price. Next, narrow down your results for properties that have a 5-star rating and are deemed "All inclusive." The first thing on the itinerary at these stays? Relaxation and indulgence.

What are the top 5-star spa hotels in Drexel Estate?

Spoil yourself with a decadent massage and other restorative treatments at The St. Regis Chicago. It's one of Drexel Estate's most popular 5-star spa escapes. Trump International Hotel & Tower Chicago and The Langham, Chicago also combine high-end accommodations with a range of wellness therapies.

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