Winnetka Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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!
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$229 per night from 29 June to 30 June
AU$229
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,295 reviews)
"Have to pay for parking plus the ac barely works"
Reviewed on 17 June 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$268 per night from 7 July to 8 July
AU$268
7 July - 8 July
includes taxes & fees
7.8/10 Good! (1,586 reviews)
"They gave my two queen beds to someone else and put us in a king with a pullout couch. That’s not too bad, but the kid sleeping on the pullout couch is 6’-1”. They tried to make up for it with drink coupons, but then the bourbon was clearly watered down. The reservation was for four adults. Not two ..."
Reviewed on 17 June 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is AU$256 per night from 28 June to 29 June
AU$256
28 June - 29 June
includes taxes & fees
8.8/10 Excellent! (2,685 reviews)
"Hotel is conveniently located nearby the Chicago O’Hare airport. The room was clean and amenities were good for our stay. Shuttle from the airport to the hotel was helpful."
Reviewed on 17 June 2026
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.
Stay near popular Winnetka attractions
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
