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Winnetka Hotel Guide - 5 Stars Hotels in Winnetka, Chicago

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Check availability on Winnetka 5 Star Hotels

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
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 group of people on a boat with a city skyline in the background.
An indoor swimming pool with a skylight, a lifeguard chair, and a potted plant.
A couple walking through a spacious lobby with marble flooring, large white floral arrangements, and a modern staircase in the background.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
United States
Edda
Rp9.238.070
Rp10.983.142 total
includes taxes & fees
15 Nov - 16 Nov
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.
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.
A modern hotel room with large windows, white furniture, and a view of tall buildings.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Cecille
Rp8.257.759
Rp9.817.647 total
includes taxes & fees
8 Nov - 9 Nov
Trump International Hotel & Tower Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
A swimming pool with a ceiling of lights, large windows, and potted plants.
A modern dining area with round tables, comfortable chairs, and a dessert display.
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Saramae
Rp9.758.272
Rp11.601.610 total
includes taxes & fees
15 Nov - 16 Nov
The Langham, Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
A modern bar area with a checkered floor, bar stools, and a bartender.
A rooftop bar with seating and a view of the city skyline at night.
A spacious hotel lobby with multiple seating areas, a grand staircase, and large windows offering views of the city.

4. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Melinda
Rp11.211.250
Rp13.329.054 total
includes taxes & fees
15 Nov - 16 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.
A bar area with a polished marble floor, bar stools, a counter with bottles, and a decorative lamp.
A couple dining on a balcony with a cityscape view.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
Downtown Chicago
United States
Luis
Rp9.529.563
Rp11.329.697 total
includes taxes & fees
15 Nov - 16 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 rooftop terrace with a view of a city skyline at dusk.
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.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
United States
Abhay
Rp8.157.305
Rp10.146.668 total
includes taxes & fees
15 Nov - 16 Nov
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.
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 rooftop terrace with a dining table, chairs, and a view of the cityscape, including the Water Tower Place building.
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
Rp9.557.366
Rp11.362.752 total
includes taxes & fees
15 Nov - 16 Nov
Park Hyatt Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.
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.
A modern lobby with a central seating area, large windows, and a decorative ceiling feature.

8. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
United States
Fred
Rp8.309.779
Rp9.879.497 total
includes taxes & fees
15 Nov - 16 Nov
The Ritz-Carlton, Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.
A rooftop pool area with city views, two lounge chairs, and a small table with a vase.
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
Rp9.918.262
Rp11.791.823 total
includes taxes & fees
12 Nov - 13 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 living room with a fireplace, a mounted TV displaying Netflix content, and a staircase leading to another level.
A spacious lounge area with multiple seating options, including sofas and chairs, and a bar area with shelves of bottles and glasses.

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
Rp2.729.267
Rp3.244.805 total
1 Nov - 2 Nov
includes taxes & fees
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Rp2.559.592
Rp3.043.098 total
3 Nov - 4 Nov
includes taxes & fees
8/10 Very good! (2,503 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
Rp3.139.150
Rp3.732.135 total
25 Oct - 26 Oct
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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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.

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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 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 Rp3.043.098
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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