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Choose from 4642 Winnetka Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
  • 40 min drive from Home Alone House
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (9,892 reviews)
We mainly go to Chicago for medical appointments and it is *so awesome* that you can actually open the windows here.That is the main reason we chose it. Because Dad has cancer we aired it out and then ran our own air purifier. No bad smells or anything, we're just being cautious because of his health. ...

Reviewed on Feb 27, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
  • 37 min drive from Home Alone House
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (3,422 reviews)
This is our new go-to in the city. Great location, very comfortable beds. Pillows are unusually small, but they brought more quickly. Large bathroom with double sinks. Breakfast buffet was excellent and plentiful. Shout out to Frank during our very late check-in. Very friendly, funny and was quick ...

Reviewed on Feb 27, 2026

Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
  • 37 min drive from Home Alone House
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,692 reviews)
Hotel is beautiful and located in the heart of everything. Starbucks outside is a plus. Breakfast is excellent and rooms are spacious. Wish they have a whirlpool

Reviewed on Feb 27, 2026

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
  • 36 min drive from Home Alone House
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (3,843 reviews)
The staff and space in the room was great! Location is outstanding!

Reviewed on Feb 27, 2026

Hilton Chicago/Magnificent Mile Suites
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
  • 37 min drive from Home Alone House
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (3,269 reviews)
Staff was helpful and professional. The room was clean and the restaurant downstairs was very good.

Reviewed on Feb 27, 2026

Eurostars Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
  • 40 min drive from Home Alone House
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,655 reviews)
Very good!

Reviewed on Feb 27, 2026

Hilton Chicago
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
  • 37 min drive from Home Alone House
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (3,101 reviews)
Great!

Reviewed on Feb 27, 2026

Aloft Chicago Mag Mile
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
  • 38 min drive from Home Alone House
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (3,464 reviews)
The room was spotless. The front desk helped make sure my reservation was taken care of despite travel delays outside of my control. Highly recommended this property and their staff

Reviewed on Feb 24, 2026

Hyatt Regency Chicago
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
  • 37 min drive from Home Alone House
Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ...
8.8/10 Excellent! (2,328 reviews)
Room was clean, great breakfast at the hotel restaurant

Reviewed on Feb 26, 2026

DoubleTree by Hilton Chicago - Magnificent Mile
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
201 N State Street Chicago IL
  • 38 min drive from Home Alone House
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9/10 Wonderful! (1,002 reviews)
Awesome stay. I love the Witt.

Reviewed on Feb 25, 2026

theWit Chicago, a Hilton Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
  • 38 min drive from Home Alone House
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,026 reviews)
Amazing place!

Reviewed on Feb 26, 2026

River Hotel
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr Chicago IL
  • 38 min drive from Home Alone House
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
9.4/10 Exceptional! (3,330 reviews)
Excellent room with amazing views. Really friendly and helpful staff. Josh at reception was extremely good to us! Excellent location centre of everything. Would definitely recommend this hotel

Reviewed on Feb 27, 2026

The Royal Sonesta Chicago Downtown
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.

Find cheap hotels in Winnetka

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If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $101. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Winnetka hotel deals at the last minute.

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Frequently Asked Questions About Winnetka hotels

Where can I find the best last-minute travel deals?

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How many hotels are there in Winnetka?

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