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Featured Winnetka 5 Star hotels

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 $602 per night from Nov 2 to Nov 3
CA $602
CA $706 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 5-star 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! (1,734 reviews)
"Excellent all around"

Reviewed on Oct 4, 2025

Opens in a new windowTrump International Hotel & Tower Chicago
The Langham, Chicago

The Langham, Chicago

5 out of 5
330 North Wabash Avenue, Chicago, IL
The price is CA $759 per night from Nov 2 to Nov 3
CA $759
CA $891 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 5-star 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! (1,003 reviews)
"Excellent stay"

Reviewed on Oct 5, 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 $907 per night from Nov 2 to Nov 3
CA $907
CA $1,065 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 5-star 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! (1,002 reviews)
"Excellent hotel, my only complaint would be the Peninsula food service. We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely ..."

Reviewed on Sep 27, 2025

Opens in a new windowThe Peninsula Chicago
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
120 East Delaware Place, Chicago, IL
The price is CA $739 per night from Nov 2 to Nov 3
CA $739
CA $868 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
9.4/10 Exceptional! (999 reviews)
"Clean room excellent staff great stay"

Reviewed on Oct 1, 2025

Opens in a new windowFour Seasons Hotel 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 $804 per night from Oct 26 to Oct 27
CA $804
CA $943 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this 5-star 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! (1,000 reviews)
"What can you say that hasn't been said about this iconic hotel - the service, accommodations and amenities are first rate."

Reviewed on Sep 29, 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 $820 per night from Nov 3 to Nov 4
CA $820
CA $963 total
Nov 3 - Nov 4
includes taxes & fees
Stay at this 5-star 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)
"Awesome room amazing tub even better service"

Reviewed on Oct 2, 2025

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 $648 per night from Oct 9 to Oct 10
CA $648
CA $760 total
Oct 9 - Oct 10
includes taxes & fees
Stay at this 5-star 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! (732 reviews)
"Very great service! From the time you walk in to check out the staff was readily available to answer our questions."

Reviewed on Oct 5, 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 $698 per night from Nov 7 to Nov 8
CA $698
CA $819 total
Nov 7 - Nov 8
includes taxes & fees
Stay at this 5-star 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)
"Be prepared to be treated like you are the most important guest at the hotel. The staff here is incredibly professional, helpful and service oriented. Every single one."

Reviewed on Sep 15, 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 $936 per night from Oct 26 to Oct 27
CA $936
CA $1,098 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this 5-star 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! (77 reviews)
"Clean room, amazing view"

Reviewed on Sep 7, 2025

Opens in a new windowThe St. Regis Chicago
Art Villa

Art Villa

5 out of 5
467 N Armour St, Chicago, IL
The price is CA $369 per night from Oct 13 to Oct 14
CA $369
CA $897 total
Oct 13 - Oct 14
includes taxes & fees
Stay at this 5-star 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