Winnetka Holidays
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Top Flight + Hotel Deals in Winnetka
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was €1,061, price is now €937 per person
€937
per person
28 Apr - 30 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on 31 Jan 2026
Top hotels in Winnetka
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €189 per night from 13 Mar to 14 Mar
€189
13 Mar - 14 Mar
includes taxes & fees
8/10 Very Good! (9,910 reviews)
Everything was clean and neat.
Reviewed on 19 Feb 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €122 per night from 4 Mar to 5 Mar
€122
4 Mar - 5 Mar
includes taxes & fees
9.4/10 Exceptional! (3,373 reviews)
The room was awesome. The hotel staff were excellent.
Reviewed on 19 Feb 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is €162 per night from 27 Feb to 28 Feb
€162
27 Feb - 28 Feb
includes taxes & fees
8.4/10 Very Good! (2,641 reviews)
Beautiful place
Reviewed on 18 Feb 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.
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Winnetka
Chicago: Navy Pier Centennial Wheel Ticket
€20
per adult
88% of travellers recommend
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- Chippewa Woods
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- Wrigley Field
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
