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Check availability on Winnetka 5 Star Hotels

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Winnetka 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.
A modern bar area with a central bar and multiple stools, surrounded by a high ceiling with a decorative light fixture.
An indoor swimming pool with a skylight, a lifeguard chair, and a potted plant.
A group of people on a boat with a city skyline in the background.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
United States
Edda
13.453.440 ₫
15.994.796 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.
A pool area with a view of a cityscape, a lounge with wicker furniture, and a person relaxing in the pool.
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.
A modern hotel room with large floor-to-ceiling windows offering a city view.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Cecille
11.933.460 ₫
14.187.687 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Trump International Hotel & Tower Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.
A modern hotel room with a large window offering a city view, three armchairs arranged around a central coffee table, and a decorative hanging plant.
A modern dining area with round tables, comfortable chairs, and a dessert display.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Saramae
13.867.392 ₫
16.486.942 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Langham, Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
A rooftop bar with seating and a view of the city skyline at night.
A modern bar area with a checkered floor, bar stools, and a bartender.
A modern indoor pool area with large windows, potted palm plants, and lounge chairs.

4. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Levi
16.816.800 ₫
19.993.623 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Peninsula Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.
A bar area with a long counter, multiple stools, and a seating area with a booth.
An indoor swimming pool with a modern design, a reception area with a sign for Waldorf Astoria Chicago, and a seating area with two people.
A couple dining on a balcony with a cityscape view.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
Downtown Chicago
United States
Luis
13.964.412 ₫
16.602.287 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Waldorf Astoria Chicago
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.
A modern lobby with a sofa, a coffee table, and a vase of flowers.
A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.
A modern hotel room with a large window, a wooden desk, a bathroom with a mirror, and a view of the cityscape.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
United States
Abhay
11.765.292 ₫
14.634.554 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.
A rooftop terrace with a dining table, chairs, and a view of the cityscape, including the Water Tower Place building.
A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.
A modern hotel room with a large bed, a seating area, a TV, and a view of the city and ocean.

7. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Tom
14.157.158 ₫
16.831.445 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Park Hyatt Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.
A modern bar area with a central bar, multiple seating options, and a large chandelier.
A spacious lobby with a central seating area, a reception desk, and a large chandelier.
A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.

8. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
United States
Fred
13.084.764 ₫
15.556.478 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Ritz-Carlton, Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
A modern hotel entrance with a prominent "STREGIS" sign, large glass windows, and a well-lit facade.
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.
A dining area with wicker chairs and tables, overlooking a marina with boats and a Ferris wheel.

9. The St. Regis Chicago

The St. Regis Chicago
Downtown Chicago
United States
Xiomara
15.031.632 ₫
17.871.108 ₫ total
includes taxes & fees
8 Nov - 9 Nov
The St. Regis Chicago
A rooftop lounge with a city skyline view, featuring a sofa set with patterned cushions and a table with drinks and snacks.
A coastal city skyline with modern high-rise buildings, a beach, and a clear blue sky.
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island with bar stools.
A living room with a fireplace, a mounted TV displaying Netflix content, and a staircase leading to another level.

10. Art Villa

Art Villa
West Town
Art Villa
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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.
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
3.936.425 ₫
4.679.986 ₫ total
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (5,527 reviews)
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
3.698.920 ₫
4.397.646 ₫ total
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,478 reviews)
The Chicago Hotel Collection Ambassador Gold Coast
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL
5.148.528 ₫
6.121.084 ₫ total
25 Oct - 26 Oct
includes taxes & fees
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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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 theatre.

See all hotels in Winnetka
A suburban street with a stone house, a tree, and a clear sky.

Top Winnetka Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winnetka?
You can find many different pricing options for 5-star hotels in Winnetka on Expedia. The amount you pay will depend on when you travel, trip length and other factors. Compare available properties for your desired dates and use our pricing and other filters to lock in the ideal upscale stay.
  • Search for the lowest price per night from 4.397.646 ₫
What makes a hotel 5 stars in Winnetka?
Outstanding guest service is integral to every 5-star hotel in Winnetka. From the minute you arrive, staff attend to your every need, whether recommending activities and tours or providing in-room massage treatments. Plus, hotels have to feature superior amenities to obtain a 5-star rating. These can include deluxe baths, on-site spa facilities, pools, gastronomic restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Winnetka?
Use Expedia's filters to find an upscale getaway in Winnetka where everything you need is included in the price. From there, narrow down your results for resorts that have 5 stars and are categorised as "All inclusive." The most important thing on the to-do list at these stays? Pure enjoyment and indulgence.

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