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Featured Winnetka 5 Star hotels

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 $611 per night from Apr 26 to Apr 27
CA $611
CA $718 total
Apr 26 - Apr 27
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! (1,005 reviews)
Yes all good

Reviewed on Mar 29, 2026

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 $730 per night from Apr 5 to Apr 6
CA $730
CA $857 total
Apr 5 - Apr 6
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! (1,007 reviews)
Awesome staff and over the top wonderful staff

Reviewed on Mar 30, 2026

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
Fully refundableReserve now, pay when you stay
The price is CA $570 per night from Apr 26 to Apr 27
CA $570
CA $670 total
Apr 26 - Apr 27
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)
Amazing

Reviewed on Apr 1, 2026

Opens in a new windowFour Seasons Hotel 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 $516 per night from Apr 7 to Apr 8
CA $516
CA $606 total
Apr 7 - Apr 8
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! (1,848 reviews)
The staff were great. Amenities were also wonderful. Will come back.

Reviewed on Mar 31, 2026

Opens in a new windowTrump International Hotel & Tower 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 $609 per night from Apr 5 to Apr 6
CA $609
CA $715 total
Apr 5 - Apr 6
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. ...
9.6/10 Exceptional! (1,000 reviews)
Amazing hotel. Excellent staff.

Reviewed on Mar 30, 2026

Opens in a new windowPark Hyatt 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 $588 per night from Apr 19 to Apr 20
CA $588
CA $690 total
Apr 19 - Apr 20
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! (1,000 reviews)
It is really a beautiful hotel .. one of the best , I have ever stayed at

Reviewed on Mar 24, 2026

Opens in a new windowWaldorf Astoria 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 $340 per night from Apr 5 to Apr 6
CA $340
CA $399 total
Apr 5 - Apr 6
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! (810 reviews)
We stayed for 2 nights. Our room was not cleaned. When asked housekeeping about cleaning our room we were told that as it was after 3 they will do a light clean up. The worst was that they did not replace our dirty coffee cups. This is very disappointing! Never expected this out of Nobu. I have never ...

Reviewed on Mar 30, 2026

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 $551 per night from Apr 12 to Apr 13
CA $551
CA $647 total
Apr 12 - Apr 13
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! (1,000 reviews)
Enjoyed a very comfortable stay.

Reviewed on Mar 30, 2026

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 $689 per night from Apr 5 to Apr 6
CA $689
CA $808 total
Apr 5 - Apr 6
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. ...
9.2/10 Wonderful! (104 reviews)
The hotel was extremely clean but the room itself reminded me of a nice condo, not a luxury hotel. Our room looked right into an apartment building with no view of the water. The restaurants, which were excellent, were highly overpriced, more so than at other nice restaurants in the city. We could ...

Reviewed on Mar 12, 2026

Opens in a new windowThe St. Regis Chicago
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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

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