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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 $666 per night from Jul 19 to Jul 20
CA $666
CA $792 total
Jul 19 - Jul 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 and the clean ...
9.6/10 Exceptional! (1,912 reviews)
"Great service"

Reviewed on Jun 30, 2026

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
Fully refundableReserve now, pay when you stay
The price is CA $711 per night from Jul 26 to Jul 27
CA $711
CA $846 total
Jul 26 - Jul 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! (1,000 reviews)
"Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't ..."

Reviewed on Jul 2, 2026

Opens in a new windowThe Langham, 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 $754 per night from Jul 19 to Jul 20
CA $754
CA $896 total
Jul 19 - Jul 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! (1,002 reviews)
"This was our first stay at a Four Seasons — if there was 6 stars for the staff, I'd give it. Upon arrival, we were running late and trying to make an event. The Bellman immediately said he'd arrange transportation for us after we quickly went to the restrooms. We come back down to discover that he ..."

Reviewed on Jul 2, 2026

Opens in a new windowFour Seasons Hotel 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 $889 per night from Jul 5 to Jul 6
CA $889
CA $1,057 total
Jul 5 - Jul 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! (1,000 reviews)
"Fantastic!"

Reviewed on Jul 1, 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 $810 per night from Jul 19 to Jul 20
CA $810
CA $963 total
Jul 19 - Jul 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)
"Beautiful property with great location in Chicago. Can’t wait to stay again."

Reviewed on Jun 28, 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 $768 per night from Aug 2 to Aug 3
CA $768
CA $913 total
Aug 2 - Aug 3
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! (1,001 reviews)
"My wife and I had a reservation for the club level and up graded to a suite at ck in . It was NOT an upgrade . We shared a wall with the lounge kitchen . The smells constantly filled our room AND the cleaning crew started in the lounge at 1 AM making it hard to sleep until they finished cleaning ..."

Reviewed on Jun 30, 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 $815 per night from Jul 9 to Jul 10
CA $815
CA $969 total
Jul 9 - Jul 10
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)
"Excellent hotel and location. 1 min away from Michigan avenue"

Reviewed on Jun 23, 2026

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 $559 per night from Jul 26 to Jul 27
CA $559
CA $665 total
Jul 26 - Jul 27
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! (881 reviews)
"The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again."

Reviewed on Jul 2, 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 $954 per night from Jul 19 to Jul 20
CA $954
CA $1,134 total
Jul 19 - Jul 20
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. ...
9.4/10 Exceptional! (124 reviews)
"👌"

Reviewed on Jun 7, 2026

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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