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
The price is NZ$266 per night from 26 May to 27 May
NZ$266
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,220 reviews)
The bar being open late is nice and the staff are very helpful.
Reviewed on 12 May 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$345 per night from 25 May to 26 May
NZ$345
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,123 reviews)
We had a great stay for our anniversary trip!
Reviewed on 12 May 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$298 per night from 25 May to 26 May
NZ$298
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (4,302 reviews)
Staff was helpful and friendly. The rooms were clean and spacious!
Reviewed on 12 May 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.
Discover the most popular places to visit in Winnetka
Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
What to do in Winnetka
Skydeck - Willis Tower Admission
NZ$75
per adult
96% of travellers recommend
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.
