Hotels in Winnetka

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Check prices for these dates

Tonight
May 4 - May 5
Tomorrow
May 5 - May 6
Next weekend
May 9 - May 11
In two weeks
May 16 - May 18

Where to stay in Winnetka?

Heart O' Chicago
Reception

Heart O' Chicago

2.0 star property
7.8 out of 10, Good, (999)
The price is $106
includes taxes & fees
$90 per night
May 5 - May 6
Heart O' 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 landmarks in Winnetka

Home Alone House

Home Alone House is in the heart of Winnetka, so why not stop by during your stay. If you have fun at Home Alone House, you'll love Chocolate Box, just a short walk away.

See properties in Home Alone House
Home Alone House

Learn more about Winnetka

Winnetka is well-known for its attractions such as Lake Michigan and Chocolate Box.

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A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Frequently asked questions

What accommodations do travelers like in Winnetka?
Guests like Chicago Marriott Suites Deerfield.
Can I book refundable accommodations in Winnetka?
If you need the flexibility to change your plans to Winnetka, most accommodations offer refundable* bookable rates. You can see these properties by searching our site and using the “fully refundable” filter to narrow down the results.
What will the weather in Winnetka be like during my visit?
The warmest months in Winnetka are usually July and August with an average temp of 70°F. January and February are the chilliest months when the average temp is 30°F. The rainiest months are May and June.
Why should I book my Winnetka hotel through Hotels.com?
There are plenty of reasons to book your Winnetka travel with us: our free cancellations on selected hotels* gives you the flexibility you’re looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

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