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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 $574 per night from Jan 11 to Jan 12
CA $574
CA $674 total
Jan 11 - Jan 12, 2026
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. ...
9.2/10 Wonderful! (998 reviews)
Expected a little better experience than we received but the Four Seasons made it right.

Reviewed on Dec 23, 2025

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 $583 per night from Jan 25 to Jan 26
CA $583
CA $684 total
Jan 25 - Jan 26, 2026
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! (1,002 reviews)
Great ex

Reviewed on Dec 25, 2025

Opens in a new windowThe Langham, 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 $649 per night from Jan 4 to Jan 5
CA $649
CA $762 total
Jan 4 - Jan 5, 2026
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 ...
9.6/10 Exceptional! (1,013 reviews)
Our stay

Reviewed on Dec 22, 2025

Opens in a new windowThe Peninsula 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 $407 per night from Jan 4 to Jan 5
CA $407
CA $477 total
Jan 4 - Jan 5, 2026
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 ...
9.4/10 Exceptional! (1,797 reviews)
Hotel stay was great, well kept, everyone was attentive

Reviewed on Dec 21, 2025

Opens in a new windowTrump International Hotel & Tower 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 $520 per night from Jan 18 to Jan 19
CA $520
CA $610 total
Jan 18 - Jan 19, 2026
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. ...
9.2/10 Wonderful! (1,002 reviews)
Don't have a pet. Room was clean. Didn't use in-room bar.

Reviewed on Dec 26, 2025

Opens in a new windowWaldorf Astoria 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 $529 per night from Jan 1 to Jan 2
CA $529
CA $621 total
Jan 1 - Jan 2, 2026
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! (999 reviews)
Great

Reviewed on Dec 17, 2025

Opens in a new windowPark Hyatt Chicago
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
155 N. Peoria Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $357 per night from Jan 2 to Jan 3
CA $357
CA $419 total
Jan 2 - Jan 3, 2026
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 ...
9.2/10 Wonderful! (764 reviews)
Well stock bar

Reviewed on Dec 23, 2025

Opens in a new windowNobu Hotel 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 $507 per night from Jan 2 to Jan 3
CA $507
CA $595 total
Jan 2 - Jan 3, 2026
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. ...
9/10 Wonderful! (1,001 reviews)
First class stay. You pay for it, but so worth it. Real hospitality, indefatigable service in a magical setting. Cannot beat the location and staff are beyond reproach.

Reviewed on Dec 25, 2025

Opens in a new windowThe Ritz-Carlton, 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 $647 per night from Jan 12 to Jan 13
CA $647
CA $759 total
Jan 12 - Jan 13, 2026
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. ...
9/10 Wonderful! (86 reviews)
All the anove

Reviewed on Dec 15, 2025

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.

Recent Winnetka hotel reviews by fellow wanderers