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

Luxury Hotels & Resorts in Winnetka from AU$152

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Check availability on Winnetka Luxury Hotels

Tonight
24 Sept - 25 Sept
Tomorrow
25 Sept - 26 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Winnetka luxury hotels

A bar area with wooden flooring, bar stools, and a counter with various bottles. There are framed pictures on the walls and a menu board.
An indoor swimming pool with clear glass walls, a lounge area with chairs, and a view of the outside.
A modern hotel room with a large window, a sofa, a dining table with chairs, and a coffee table.
A spacious ballroom with a high ceiling, large windows offering a city view, and a stage for presentations.

1. DoubleTree by Hilton Chicago - North Shore Conference Center

DoubleTree by Hilton Chicago - North Shore Conference Center
Skokie
  • Experience indoor and outdoor pools paired with exceptional dining at this luxury Chicago hotel with premium beds.
AU$223
includes taxes & fees
5 Oct - 6 Oct
DoubleTree by Hilton Chicago - North Shore Conference Center
An outdoor seating area with wicker chairs and a sofa, surrounded by trees and a building facade.
A modern hotel room with a sectional sofa, a round coffee table, a bed, and a desk with a lamp.
A hotel entrance with a prominent 'Renaissance' sign, modern architecture, and a clear sky.
A luxurious living room with a plush sofa, decorative lamps, and a chandelier.

2. Renaissance Chicago North Shore Hotel

Renaissance Chicago North Shore Hotel
Northbrook
  • Upscale retreat with pillowtop beds and designer touches provides 3 exceptional restaurants near Chicago Botanic Garden.
AU$213
includes taxes & fees
11 Oct - 12 Oct
Renaissance Chicago North Shore Hotel
A balcony with a round table and two chairs, a view of a lake, and a cloudy sky.
A bar area with multiple TVs displaying golf, a variety of liquor bottles, and wooden bar stools.
A spacious lobby with a round table, chairs, a potted plant, and a chandelier.
A golf course with a pond reflecting the surroundings, a brick building with multiple windows, and trees around the area.

3. The Glen Club

The Glen Club
Glenview
AU$256
includes taxes & fees
27 Sept - 28 Sept
The Glen Club
A spacious lobby with a fireplace, comfortable seating, and a high ceiling with multiple balconies.
A heated indoor pool area with a hot tub, seating, and large windows.
A multi-story building with a sign reading "Embassy Suites."
A spacious outdoor lounge area with multiple seating options including sofas and chairs, arranged around a central coffee table.

4. Embassy Suites by Hilton Chicago North Shore Deerfield

Embassy Suites by Hilton Chicago North Shore Deerfield
Deerfield
  • Upscale retreat with indoor pool, spa pool, and premium dining near Chicago's north shore.
AU$196
includes taxes & fees
11 Oct - 12 Oct
Embassy Suites by Hilton Chicago North Shore Deerfield
A spacious lobby with a central seating area, a piano, and a large window overlooking a garden.
An outdoor seating area with sofas, tables, and chairs, surrounded by greenery and a building with an arched entrance.
A hotel corridor with multiple tables and decorative vases, featuring a modern chandelier and framed artwork on the walls.
A conference room with rows of chairs facing a large screen, a podium, and a blue-lit ceiling.

5. Hyatt Regency Deerfield

Hyatt Regency Deerfield
Deerfield
  • Luxury awaits at this Chicago suburban hotel with refined rooms, indoor pool, and upscale dining.
AU$203
includes taxes & fees
27 Sept - 28 Sept
Hyatt Regency Deerfield
A spacious lobby with a central coffee table, sofas, and a large mirror.
A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.
A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.
A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

6. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
AU$272
includes taxes & fees
25 Oct - 26 Oct
The Chicago Hotel Collection Ambassador Gold Coast
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.
A modern hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.

7. The Wade

The Wade
Downtown Chicago
  • Luxurious lakeside retreat in city centre Chicago offers pillowtop beds, designer toiletries, and stunning views near Michigan Avenue.
AU$252
includes taxes & fees
27 Sept - 28 Sept
The Wade
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.
A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.
A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

8. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
AU$542
includes taxes & fees
27 Sept - 28 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.
A modern kitchen with a central island, bar stools, a chandelier, and a large flat-screen TV.
A modern hotel room with a large bed, a chair, a small table, and a window with a view.
A bar area with a long counter, multiple stools, and a modern chandelier.

9. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
AU$273
includes taxes & fees
27 Sept - 28 Sept
Claridge House Chicago, Tapestry Collection by Hilton
A modern building with the name 'SENIORAL' prominently displayed on the facade.
A modern kitchen with a built-in microwave, stove, and dishwasher, large windows with city views, and a dining area with a table and chairs.
A modern kitchen with a large island, bar stools, and a view of the city skyline.
A balcony with a glass railing, a table, and four chairs.

10. Sentral Michigan Avenue

Sentral Michigan Avenue
Downtown Chicago
AU$295
includes taxes & fees
27 Sept - 28 Sept
Sentral Michigan Avenue
View all properties

Top Winnetka Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Nice place"
Duriel 2-night trip
Posted 1 hour ago
InterContinental Chicago Magnificent Mile by IHG
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Much better experience than anticipated based off of reviews. Great location!"
Jade 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Wonderful location in the heart of downtown Chicago and the River Walk. Very welcoming staff set this stay apart!"
Lori 2-night trip
Posted 5 hours ago
L7 Chicago by LOTTE
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"Nice"
Nathaniel 3-night trip
Posted 5 hours ago
The Chicago Hotel Collection - Magnificent Mile
River Hotel

River Hotel

8/10 Good
"Elevator was broken, took 15 minutes each time I needed it"
Scott 2-night trip
Posted 9 hours ago
River Hotel
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

10/10 Excellent
"So amazing! 100% want to stay again!"
Cassandra 1-night trip
Posted 11 hours ago
Travelodge by Wyndham Downtown Chicago
Hilton Chicago

Hilton Chicago

10/10 Excellent
"Very clean. Great location. Close to shopping, restaurants and the lake. Highly recommend"
Lilian 1-night trip
Posted 11 hours ago
Hilton Chicago
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"This is my new favorite hotel in the city. ❤️"
Adam 1-night trip
Posted 19 hours ago
Fairmont Chicago at Millennium Park
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Excellent service! Everyone was helpful and fry! Great experience and location"
Brittany 1-night trip
Posted 2 days ago
The Royal Sonesta Chicago Downtown

Frequently asked questions

Are you looking for a luxury hotel for your stay in Winnetka?
Use Expedia to arrange your flight to Chicago, IL (PWK-Chicago Executive) airport or Chicago O'Hare International Airport (ORD) airport, and then choose from a variety of places to stay that will deliver the luxury you seek. Amenities are an important consideration when you plan a holiday, so we make it easy to get what you'd like to make your stay special. If you want a posh hotel that has fine dining, a spa or several swimming pools, Expedia can help you find the best luxury hotel experience that Winnetka offers. Winnetka has some interesting things to see and do including Lake Michigan and Maple Street Beach, so you might want to take in the local sights during your visit.
When can I expect good weather in Winnetka?
Planning for the weather is a good way to make your trip to Winnetka relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Winnetka is 1216 mm.
What's there to see and do in Winnetka?
When you're in Winnetka, enjoy exploring the sights and attractions here including Lake Michigan, Maple Street Beach and Elder Lane Beach. If you have extra time while you're in the area, you might want to stop by Wrigley Field and Navy Pier.
How can I get around Winnetka?
It's easier to get around town comfortably when you know your options. To venture out into the surrounding area, hop aboard a train at Winnetka Station or Winnetka Indian Hill Station.

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