Stinson Memorial Library Anna Illinois Listed on the National Register  Funded by Anna businessman Robert Burns Stinson, designed by Walter Burley Griffin who studied under Frank Lloyd Wright.

Luxury Hotels & Resorts in Winnetka from AU$229

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Our top choices for Winnetka luxury hotels

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, (2,559 reviews)
The price is AU$412
includes taxes & fees
30 June - 1 July
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, (3,525 reviews)
The price is AU$392
includes taxes & fees
5 July - 6 July
Hyatt Regency Chicago

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,814 reviews)
The price is AU$304
includes taxes & fees
5 July - 6 July
Omni Chicago Hotel

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,007 reviews)
  • cleanliness
    Luxuriate in city centre Chicago at this full-service spa hotel steps from Michigan Avenue and the Riverwalk.
The price is AU$363
includes taxes & fees
30 June - 1 July
theWit Chicago, a Hilton Hotel

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (1,607 reviews)
The price is AU$259
includes taxes & fees
5 July - 6 July
The Chicago Hotel Collection Ambassador Gold Coast

Pendry Chicago

Pendry Chicago
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,134 reviews)
  • cleanliness
    Indulge in architectural splendour and upscale amenities at this Art Deco Chicago hotel, where luxury meets city centre convenience.
The price is AU$453
includes taxes & fees
5 July - 6 July
Pendry Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,401 reviews)
The price is AU$346
includes taxes & fees
1 July - 2 July
Swissotel - Chicago

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,672 reviews)
The price is AU$419
includes taxes & fees
5 July - 6 July
Sheraton Grand Chicago Riverwalk

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,471 reviews)
The price is AU$344
includes taxes & fees
29 June - 30 June
Hotel Riu Plaza Chicago

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,202 reviews)
The price is AU$452
includes taxes & fees
6 July - 7 July
Fairmont Chicago at Millennium Park
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.

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