Winnetka Holidays from AU$3,718
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Your Winnetka Holiday
When a city stay is calling, answer it with a holiday package to Winnetka. With all your travel needs in place before you leave, all you have to do here is focus on having the time of your life. Northwestern University, Chicago Botanic Garden and The Glen Club are just some of the many sights worth exploring during your trip to Winnetka. Expedia can help you escape your daily routine. Tailor your holiday to Winnetka to suit your style of travel, whatever that may be!
The Latest Winnetka Holiday Deals
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was AU$5,267, price is now AU$4,373 per person
AU$4,373
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (3,374 reviews)
This hotel was nearly perfect! Great staff. Great location. Clean. My only complaint was the ice machine was broken on our floor. We reported it to staff 3 separate occasions and it wasn’t fixed in the 5 days we were there. Hotel is located on a busy street so there is some noise but if that Doesn't bother you… this is perfect. Very walkable location! The staff there are fantastic. From the moment you walk in until the moment you leave. They understand the assignment. Highly recommend.
Reviewed on 21 Oct 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was AU$4,694, price is now AU$3,955 per person
AU$3,955
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on 20 Oct 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was AU$4,512, price is now AU$3,955 per person
AU$3,955
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
Everything was amazing. I will definitely be back!
Reviewed on 23 Oct 2025
Arlo Chicago
Downtown Chicago
Price was AU$4,597, price is now AU$4,062 per person
AU$4,062
per person
29 Nov - 5 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
We had an amazing time staying at the Arlo. The staff was very friendly, the check-in/check-out process was very fast. The room was always clean. The location of the hotel is extremely convenient. Everything was awesome. I’m 100% coming back when I’m in Chicago again.
Reviewed on 22 Oct 2025
Winnetka Holiday
Winnetka Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 12,500 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Rosemont Theatre, Riviera Theatre and Parkway Bank Park Entertainment District |
Our pick of the best Winnetka Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$169 per night from 24 Nov to 25 Nov
AU$169
24 Nov - 25 Nov
includes taxes & fees
7.8/10 Good! (9,498 reviews)
The website for the gazebo restaurant within the hotel said there was an extensive menu. When you get down to the place it’s a small buffett set up which was similar to any other continental breakfast with some cereal, muffins, fruit, some biscuits, bacon and sausage etc. There was also a man at ...
Reviewed on 20 Oct 2025
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is AU$250 per night from 23 Nov to 24 Nov
AU$250
23 Nov - 24 Nov
includes taxes & fees
8.8/10 Excellent! (1,943 reviews)
Great location if you have meetings at the Mart which you can reach through escalator and a bridge that takes you directly to the second floor. The hotel is well run Good breakfast and friendly staff. Rooms are clean but they should start “refreshing” some of the features like carpets which seem ...
Reviewed on 13 Oct 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$202 per night from 16 Nov to 17 Nov
AU$202
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (3,133 reviews)
Every think was wonderful except the heater wasn’t working and the toilet was loose.
Reviewed on 19 Oct 2025
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.
Discover the most popular places to visit in Winnetka
Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
Grant Park
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
What to do in Winnetka
Skydeck - Willis Tower Admission
AU$67
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
AU$37
per adult
84% of travellers recommend
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