5 Stars Hotels in Winnetka, Illinois from CA $499

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Check prices for these dates

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

Our top choices for Winnetka 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, (1,000 reviews)
"Great place to stay in Chicago!"
United States
ryan
The price is CA $685
CA $814 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 $645
CA $766 total
includes taxes & fees
Nov 29 - Nov 30
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 $838
CA $997 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 $729
CA $867 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, (1,000 reviews)
"Great hotel"
United States
Luis
The price is CA $626
CA $744 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, (1,000 reviews)
"Very helpful staff good for families"
United States
Krikour
The price is CA $550
CA $654 total
includes taxes & fees
Dec 6 - Dec 7
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, (963 reviews)
"Great location Helpful staff"
United States
Abhay
The price is CA $499
CA $629 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, (1,001 reviews)
"Excellent experience. I’d recommend this property for their outstanding service and updated rooms."
United States
Marissa
The price is CA $614
CA $730 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 $751
CA $893 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 Winnetka Hotel Reviews

A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.
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 Winnetka

Five Star Hotels in Winnetka

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 Winnetka 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 Winnetka and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Winnetka

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 Winnetka

The results are in, and Winnetka 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 Winnetka! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Winnetka 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 Winnetka?

You can find a variety of pricing options for 5-star hotels in Winnetka on Expedia. How much you'll pay will depend on when you plan to travel, trip length and other factors. Compare all of the available accommodations for your preferred dates and use our pricing and other filters to land the perfect high-end stay.

  • Search for the lowest price per night from CA $499

What makes a hotel 5 stars in Winnetka?

From gourmet restaurants and 24-hour fitness centres to swimming pools and dreamy bedding, the 5-star experience in Winnetka is all about relaxation and luxury. But it requires more than just upscale amenities to earn a 5-star rating. Accommodations must also provide superior services like massage treatments, on-site dry cleaning and laundry and 24-hour concierge services.

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

Expedia's filter tool is the best way to narrow down what you want. Select "5-star" and "All inclusive" to see the most luxurious properties in Winnetka where your lodging, meals, entertainment and activities are included in the price. At these getaways, your vacation is pure leisure from the moment you enter the lobby.

Are there any 5-star vacation rentals in Winnetka?

Although there aren't any 5-star vacation rentals in Winnetka on our site, we have a range of escapes that promise a fabulous getaway. Discover one that suits your style by checking out our vacation rentals in Winnetka.

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