Luxury Hotels & Resorts in Winnetka from AU$145

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Winnetka Luxury Hotels

Next weekend
In two weeks

Our top choices for Winnetka luxury hotels

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,856 reviews)
  • cleanliness
    Immerse in riverside elegance at this 5-star Chicago hotel offering deep-soaking tubs, pillowtop beds, and full-service spa indulgence.
The price is AU$737
includes taxes & fees
25 May - 26 May
Trump International Hotel & Tower Chicago

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,482 reviews)
The price is AU$361
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,504 reviews)
The price is AU$413
includes taxes & fees
24 May - 25 May
Hyatt Regency Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2,841 reviews)
The price is AU$275
includes taxes & fees
10 May - 11 May
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,296 reviews)
The price is AU$376
includes taxes & fees
27 May - 28 May
Swissotel - Chicago

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,034 reviews)
  • cleanliness
    Elegant city centre sanctuary boasts historic charm, luxury spa treatments, and a stunning indoor pool.
The price is AU$377
includes taxes & fees
26 May - 27 May
InterContinental Chicago Magnificent Mile by IHG

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2,939 reviews)
The price is AU$186
includes taxes & fees
25 May - 26 May
Freehand Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,770 reviews)
The price is AU$256
includes taxes & fees
25 May - 26 May
Hilton Chicago

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,626 reviews)
The price is AU$405
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,034 reviews)
The price is AU$261
includes taxes & fees
27 May - 28 May
Hotel Riu Plaza Chicago
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.

Top Winnetka Hotel Reviews

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 Chocolate Box, 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, Chocolate Box and Maple Street Beach. If you have extra time while you're in the area, you might want to stop by Wrigley Field and Naval Base Great Lakes.
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.

Explore a world of travel with Expedia