Explore top 2026 5 Star Hotels in Winnetka
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Top Winnetka 5 Star hotels
The Langham, Chicago
330 North Wabash Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$439 nightly
The price is $516 total per night from Apr 26 to Apr 27
$516 total
Apr 26 - Apr 27
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...
9.8/10 Exceptional! (1,005 reviews)
Yes all good
Reviewed on Mar 29, 2026
The Peninsula Chicago
108 East Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$525 nightly
The price is $616 total per night from Apr 5 to Apr 6
$616 total
Apr 5 - Apr 6
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and babysitting. ...
9.8/10 Exceptional! (1,006 reviews)
Awesome staff and over the top wonderful staff
Reviewed on Mar 30, 2026
Four Seasons Hotel Chicago
120 East Delaware Place Chicago IL
$410 nightly
The price is $481 total per night from Apr 12 to Apr 13
$481 total
Apr 12 - Apr 13
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business ...
9.4/10 Exceptional! (1,003 reviews)
Great licat
Reviewed on Mar 27, 2026
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$371 nightly
The price is $436 total per night from Apr 6 to Apr 7
$436 total
Apr 6 - Apr 7
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly ...
9.4/10 Exceptional! (1,848 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on Mar 31, 2026
Park Hyatt Chicago
800 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$438 nightly
The price is $514 total per night from Apr 5 to Apr 6
$514 total
Apr 5 - Apr 6
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...
9.6/10 Exceptional! (1,002 reviews)
Amazing hotel. Excellent staff.
Reviewed on Mar 30, 2026
Waldorf Astoria Chicago
11 E. Walton Street Chicago IL
Fully refundableReserve now, pay when you stay
$422 nightly
The price is $496 total per night from Apr 19 to Apr 20
$496 total
Apr 19 - Apr 20
Total with taxes and fees
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi ...
9.4/10 Exceptional! (1,002 reviews)
It is really a beautiful hotel .. one of the best , I have ever stayed at
Reviewed on Mar 24, 2026
Nobu Hotel Chicago
155 N. Peoria Street Chicago IL
Fully refundableReserve now, pay when you stay
$339 nightly
The price is $398 total per night from Apr 5 to Apr 6
$398 total
Apr 5 - Apr 6
Total with taxes and fees
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. There's a bar/lounge on site, and a 24-hour ...
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
The Ritz-Carlton, Chicago
160 E Pearson Street Chicago IL
Fully refundableReserve now, pay when you stay
$396 nightly
The price is $465 total per night from Apr 12 to Apr 13
$465 total
Apr 12 - Apr 13
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, ...
9.2/10 Wonderful! (1,000 reviews)
Enjoyed a very comfortable stay.
Reviewed on Mar 30, 2026
The St. Regis Chicago
401 East Upper Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$495 nightly
The price is $581 total per night from Apr 5 to Apr 6
$581 total
Apr 5 - Apr 6
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public ...
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
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Winnetka Resorts & 5 Star Hotels
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 5-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
Hyatt Regency Chicago
5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"No complaints about the room or breakfast or bar or restaurant. Great view of the river and lake from our room. Enjoyed the convenient location. "
A verified traveler stayed at Hyatt Regency Chicago
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