Are there any 5-star vacation rentals in Winnetka?

Although you won't find any 5-star vacation rentals in Winnetka on our site, we have a range of stays that promise a memorable getaway. Find one that matches your style by searching our vacation rentals in Winnetka .

The Best 5 Star Hotels in Winnetka, IL from SAR 473

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Our top choices for Winnetka 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.

1. Four Seasons Hotel Chicago

Downtown Chicago

ryan

SAR 1,896 total

includes taxes & fees

13 Dec - 14 Dec

A cityscape with a river, a bridge, and a dining area with tables and chairs.

2. Trump International Hotel & Tower Chicago

Downtown Chicago

Matthew

SAR 1,757 total

includes taxes & fees

13 Dec - 14 Dec

A rooftop bar with seating and a view of the city skyline at night.

3. The Peninsula Chicago

Downtown Chicago

Vincent Haley

SAR 2,343 total

includes taxes & fees

13 Dec - 14 Dec

A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

4. The Langham, Chicago

Downtown Chicago

Talia

SAR 1,941 total

includes taxes & fees

13 Dec - 14 Dec

A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

5. Waldorf Astoria Chicago

Downtown Chicago

Loai

SAR 1,953 total

includes taxes & fees

13 Dec - 14 Dec

A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.

6. The Ritz-Carlton, Chicago

Downtown Chicago

Krikour

SAR 1,656 total

includes taxes & fees

13 Dec - 14 Dec

A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.

7. Nobu Hotel Chicago

Downtown Chicago

Mauro

SAR 1,580 total

includes taxes & fees

26 Nov - 27 Nov

A couple dining at a table with a view of a cityscape and a sunset.

8. Park Hyatt Chicago

Downtown Chicago

Tom

SAR 1,896 total

includes taxes & fees

13 Dec - 14 Dec

A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.

9. The St. Regis Chicago

Downtown Chicago

Alise

SAR 2,512 total

includes taxes & fees

3 Dec - 4 Dec

A rooftop lounge with a city skyline view, featuring a sofa set with patterned cushions and a table with drinks and snacks.

10. Art Villa

West Town

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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winnetka.

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

SAR 686

SAR 805 total

12 Dec - 13 Dec

includes taxes & fees

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Pool Spa Hot tub Breakfast included Waterpark

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.

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 theater.

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A suburban street with a stone house, a tree, and a clear sky.

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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 a 5-star hotel in Winnetka on Expedia. How much you'll pay will depend on your travel dates, trip length and other factors. Compare all of the available accommodations for your preferred dates and use our pricing and other filters to score the ideal upscale stay.

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What makes a hotel 5 stars in Winnetka?

Exceptional guest service is integral to every 5-star hotel in Winnetka. From the second you arrive, staff attend to your every need, whether answering room service calls 24/7 or providing a nightly turn-down service. On top of that, hotels must offer top-rate conveniences to meet the standard for a 5-star rating. These can include luxury bath products, spas or saunas, swimming pools, fine dining restaurants and knowledgeable concierge.

Are there any 5-star all-inclusive resorts in Winnetka?

Expedia's filter tool is the quickest way to find exactly what you're looking for. Check the "All inclusive" and "5-star" boxes to see the most luxurious properties in Winnetka where your meals, lodging, activities and entertainment are included in the price. At these getaways, your trip is absolute indulgence from the moment you enter the lobby.

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