Winnetka Holidays
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Winnetka Holiday
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 NZ$287 per night from 30 June to 1 July
NZ$287
30 June - 1 July
includes taxes & fees
8/10 Very good! (10,133 reviews)
"The hotel is a bit run down, but my room was very clean. The breakfast was good, although it is not included, and for some reason I thought it was. The receptionist was amazing. She was very kind and allowed me to check in early, which I really appreciated. The location is also excellent. I’m giving ..."
Reviewed on 26 June 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$381 per night from 5 July to 6 July
NZ$381
5 July - 6 July
includes taxes & fees
9.2/10 Wonderful! (1,826 reviews)
"Room clean and bed comfortable"
Reviewed on 27 June 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$347 per night from 5 July to 6 July
NZ$347
5 July - 6 July
includes taxes & fees
9/10 Wonderful! (4,464 reviews)
"Location was great. Everything at the hotel from checkin to chef out was very smooth."
Reviewed on 26 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
What to do in Winnetka
Chicago Sightseeing River and Lake Cruise
NZ$78
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
