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Find 5 Star Hotels in Winnetka, IL from $170

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Check availability on Winnetka 5 Star Hotels

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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.
A group of people on a boat with a city skyline in the background.
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
$515 nightly
$612 total
Nov 15 - Nov 16
Total with taxes and fees
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.
A modern hotel room with large windows, white furniture, and a view of tall buildings.
A modern hotel room with large floor-to-ceiling windows offering a city view.
A pool area with a view of a cityscape, a lounge with wicker furniture, and a person relaxing in the pool.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Cecille
$461 nightly
$548 total
Nov 1 - Nov 2
Total with taxes and fees
Trump International Hotel & Tower Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
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 spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.
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
$544 nightly
$647 total
Nov 15 - Nov 16
Total with taxes and fees
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
$625 nightly
$743 total
Nov 15 - Nov 16
Total with taxes and fees
The Peninsula Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.
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.
A bar area with a long counter, multiple stools, and a seating area with a booth.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
Downtown Chicago
United States
Luis
$531 nightly
$632 total
Nov 15 - Nov 16
Total with taxes and fees
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 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.
A modern lobby with a sofa, a coffee table, and a vase of flowers.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
United States
Abhay
$476 nightly
$566 total
Nov 1 - Nov 2
Total with taxes and fees
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 woman sitting by a window with a city view, holding a cup and saucer.

7. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Tom
$533 nightly
$633 total
Nov 15 - Nov 16
Total with taxes and fees
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 modern bar area with a central bar, multiple seating options, 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
$463 nightly
$551 total
Nov 15 - Nov 16
Total with taxes and fees
The Ritz-Carlton, Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
A rooftop pool area with city views, two lounge chairs, and a small table with a vase.
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.
A modern hotel entrance with a prominent "STREGIS" sign, large glass windows, and a well-lit facade.

9. The St. Regis Chicago

The St. Regis Chicago
Downtown Chicago
United States
Xiomara
$554 nightly
$659 total
Nov 12 - Nov 13
Total with taxes and fees
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
$152 nightly
$181 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (5,526 reviews)
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
$143 nightly
$170 total
Nov 1 - Nov 2
Total with taxes and fees
8/10 Very Good! (2,502 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
$175 nightly
$208 total
Oct 25 - Oct 26
Total with taxes and 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 theater.

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

Top Winnetka Hotel Reviews

Find out more about Winnetka

There's nothing wrong with enjoying the finer things in life. Indulge your every whim on your impending break. There's no reason to delay a getaway to Winnetka any longer. You'll join the multitudes of vacationers who have made Winnetka so fashionable in the last few seasons. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Winnetka and indulge in the finer things in life for a while.

Get a Great Deal on 5-Star Hotels in Winnetka

You'll have a wonderful time at one of these 5-star hotels. Excellent service, delicious meals, and attentive guest service are all at your fingertips. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready for a wonderful adventure. What creature comforts do you want in your lodging? A concierge to help you suggest the next attraction to visit? A rejuvenating facial treatment to help your cares fall away? Comfortable beds, piping hot coffees, and even spectacular views...these hotels will astonish you. Want to see for yourself? Explore our listings and pick the perfect accommodation for your needs.

Can't wait to get outside? We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Winnetka are the perfect place to relax after a busy day.

Your Getaway Starts Today

The results are in, and Winnetka 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. Your great getaway is just a mouse-click away. Select one of our Winnetka 5-star hotels today and relax in luxe surroundings 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 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.
  • Search for the lowest price per night from $170
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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