Winnetka Holidays
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Top Flight + Hotel Deals in Winnetka
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,505, price is now €1,005 per person
€1,005
per person
1 Feb - 6 Feb
found 9 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance.
The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return.
Mr. & Mrs.S
Reviewed on 17 Nov 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €952, price is now €662 per person
€662
per person
1 Feb - 6 Feb
found 11 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on 28 Oct 2025
Pendry Chicago
Downtown Chicago
Price was €937, price is now €670 per person
€670
per person
1 Feb - 6 Feb
found 11 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.
Reviewed on 18 Nov 2025
Top hotels in Winnetka
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is €94 per night from 7 Dec to 8 Dec
€94
7 Dec - 8 Dec
includes taxes & fees
8.4/10 Very Good! (5,271 reviews)
Great location. Fantastic staff. Breakfast was absolutely amazing. Only issue we had was insufficient bath towels and front desk resolved this quickly. I would gladly stay here again without a doubt
Reviewed on 18 Nov 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is €126 per night from 21 Dec to 22 Dec
€126
21 Dec - 22 Dec
includes taxes & fees
8.4/10 Very Good! (2,067 reviews)
The lobby is stunning. The Christmas tree and decorations appeared overnight and were a lovely surprise. Beautiful hotel
Reviewed on 17 Nov 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is €85 per night from 7 Dec to 8 Dec
€85
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,290 reviews)
I loved that everything was in walking distance. It was very clean. The hospitality service was excellent! Very kind and friendly!
Reviewed on 14 Nov 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.
Popular places to visit
Wrigley Field
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(14 reviews)
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
4/5(125 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Winnetka
Skydeck - Willis Tower Admission
€38
per adult
96% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
84% of travellers recommend
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Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
