5 Stars Hotels in Winnetka, Chicago from CA $178

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Our top choices for Winnetka 5-star hotels

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,000 reviews)
"Beautiful and in walking distance to so many shops and cafes! We had a great stay. "
United States
Jazimine
The price is CA $786
CA $934 total
includes taxes & fees
May 24 - May 25
Four Seasons Hotel Chicago

The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,001 reviews)
"Highly recommend, super nice rooms and very polite staff."
United States
Alexander
The price is CA $611
CA $726 total
includes taxes & fees
May 25 - May 26
The Langham, Chicago

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,852 reviews)
"Great staff, facilities, esp the fitness & spa"
United States
Joshua
The price is CA $610
CA $725 total
includes taxes & fees
May 25 - May 26
Trump International Hotel & Tower Chicago

The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,000 reviews)
"A beautiful hotel with an outstanding staff in a superb location. "
United States
Rose
The price is CA $829
CA $986 total
includes taxes & fees
May 25 - May 26
The Peninsula Chicago

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,002 reviews)
"Enjoyed my stay and would definitely recommend to a friend."
United States
Geneva
The price is CA $574
CA $683 total
includes taxes & fees
May 25 - May 26
The Ritz-Carlton, Chicago

Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,002 reviews)
"Great place to stay . The staff was friendly and helpful !!!"
United States
Denise
The price is CA $700
CA $833 total
includes taxes & fees
May 25 - May 26
Waldorf Astoria Chicago

Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (829 reviews)
"loved the property and restaurant"
United States
Kathryn
The price is CA $389
CA $463 total
includes taxes & fees
May 25 - May 26
Nobu Hotel Chicago

Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,001 reviews)
"Great property "
United States
Kerry
The price is CA $745
CA $886 total
includes taxes & fees
May 25 - May 26
Park Hyatt Chicago

The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (108 reviews)
"Great hotel, large pool - although I wish it was a bit warmer for my liking. The hot sauna though was a nice addition ( there is no hut tub in the pool area). Large gym was also great- unbelievable views of Lake Michigan and Navy Pier! "
United States
Beata
The price is CA $868
CA $1,032 total
includes taxes & fees
May 25 - May 26
The St. Regis Chicago

Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2 reviews)
Art Villa
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Learn more about Winnetka

Elegant North Shore homes line the streets near Lake Michigan beaches where locals picnic during summer festivals. Explore the historic Crow Island School's architecture or catch a show at the Winnetka Community House theatre.

Stinson Memorial Library Anna Illinois Listed on the National Register  Funded by Anna businessman Robert Burns Stinson, designed by Walter Burley Griffin who studied under Frank Lloyd Wright.

Top Winnetka Hotel Reviews

Find out more about Winnetka

Five Star Hotels in Winnetka

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Winnetka so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Winnetka and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Winnetka

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Winnetka

The results are in, and Winnetka 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Winnetka! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Winnetka today and settle down in the lap of luxury tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winnetka?
You can find a variety of pricing options for 5-star hotels in Winnetka on Expedia. How much you'll pay will depend on when you plan to travel, trip length and other factors. Compare all of the available accommodations for your preferred dates and use our pricing and other filters to land the perfect high-end stay.

  • Search for the lowest price per night from CA $178

What makes a hotel 5 stars in Winnetka?
From gourmet restaurants and 24-hour fitness centres to swimming pools and dreamy bedding, the 5-star experience in Winnetka is all about relaxation and luxury. But it requires more than just upscale amenities to earn a 5-star rating. Accommodations must also provide superior services like massage treatments, on-site dry cleaning and laundry and 24-hour concierge services.
Are there any 5-star all-inclusive resorts in Winnetka?
Expedia's filter tool is the best way to narrow down what you want. Select "5-star" and "All inclusive" to see the most luxurious properties in Winnetka where your lodging, meals, entertainment and activities are included in the price. At these getaways, your vacation is pure leisure from the moment you enter the lobby.

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