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Featured Winnetka 5 Star hotels

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
120 East Delaware Place Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $701 per night from May 25 to May 26
CA $701
CA $834 total
May 25 - May 26
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,002 reviews)
Este hotel están bastante bien situado cerca de tiendas sobre todo Bloomingdale que están en el mismo edificio es una buena opción

Reviewed on May 18, 2026

Opens in a new windowFour Seasons Hotel Chicago
The Langham, Chicago

The Langham, Chicago

5 out of 5
330 North Wabash Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $813 per night from Jun 11 to Jun 12
CA $813
CA $967 total
Jun 11 - Jun 12
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.8/10 Exceptional! (1,006 reviews)
Fantastic hotel and amazing spa! Beautiful room with fantastic staff

Reviewed on May 16, 2026

Opens in a new windowThe Langham, Chicago
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
401 N Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $614 per night from May 25 to May 26
CA $614
CA $729 total
May 25 - May 26
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (1,874 reviews)
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Reviewed on May 17, 2026

Opens in a new windowTrump International Hotel & Tower Chicago
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
108 East Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $997 per night from May 21 to May 22
CA $997
CA $1,185 total
May 21 - May 22
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
9.8/10 Exceptional! (1,005 reviews)
Great stay!

Reviewed on May 17, 2026

Opens in a new windowThe Peninsula Chicago
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
11 E. Walton Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $707 per night from May 25 to May 26
CA $707
CA $841 total
May 25 - May 26
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,001 reviews)
Wonderful Hotel will definitely be looking forward to going back.

Reviewed on Apr 25, 2026

Opens in a new windowWaldorf Astoria Chicago
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5 out of 5
160 E Pearson Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $666 per night from May 24 to May 25
CA $666
CA $791 total
May 24 - May 25
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,002 reviews)
Excellent experience

Reviewed on May 11, 2026

Opens in a new windowThe Ritz-Carlton, Chicago
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
800 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $749 per night from May 25 to May 26
CA $749
CA $891 total
May 25 - May 26
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Opens in a new windowPark Hyatt Chicago
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
155 N. Peoria Street Chicago IL
The price is CA $524 per night from May 25 to May 26
CA $524
CA $623 total
May 25 - May 26
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
9.4/10 Exceptional! (848 reviews)
For $900 a night, the bathroom should at least very clean and not covered in mold and mildew

Reviewed on May 18, 2026

Opens in a new windowNobu Hotel Chicago
The St. Regis Chicago

The St. Regis Chicago

5 out of 5
401 East Upper Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $985 per night from Jun 2 to Jun 3
CA $985
CA $1,170 total
Jun 2 - Jun 3
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Opens in a new windowThe St. Regis Chicago
Art Villa

Art Villa

5 out of 5
467 N Armour St Chicago IL
Book a stay at this luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk ...
10/10 Exceptional! (2 reviews)

Reviewed on Aug 12, 2025

Opens in a new windowArt Villa
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Five Star Hotels in Winnetka

Looking for your own little slice of heaven during your next trip? Check out all the best 5 star hotels in Winnetka to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the five star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Winnetka 5 star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5 star hotels in Winnetka before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

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