
Winnetka Holidays
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Top Flight + Hotel Deals in Winnetka
Price found within the past 48 hours. Click for updated prices.




Hilton Chicago O'Hare Airport
O'Hare
Price was €909, price is now €689 per person
€689
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
Airport adjacent. It is terribly overpriced. The one saving grace is LOCATION.
Reviewed on 3 Oct 2025

The Peninsula Chicago
Downtown Chicago
Price was €2,048, price is now €1,564 per person
€1,564
per person
29 Dec - 2 Jan
found 21 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Excellent hotel, my only complaint would be the Peninsula food service.
We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely wasn’t. The whole Peking duck was arranged haphazardly on the plate, the skin was not really crispy, and the taste experience was completely lackluster.
As to the main dining room the service continues, as always, to be erratic and frequently slow. Food is sometimes served hot, sometimes not.
The room service on our checkout day was absolutely abysmal. We both ordered eggs Benedict and both orders were served not a degree above room temperature. The hollandaise sauce was so cold it had solidified.
There really is no excuse for this.
And unfortunately we did not have time to return the order as we had a plane to catch and we were running a bit behind.
For an otherwise professional hotel the food service and quality is sadly lacking. It leads one to believe that the F&B manager could be a nephew, a cousin, or some other family member need of a job.
Reviewed on 27 Sept 2025
Top hotels in Winnetka

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (9,286 reviews)
"The lobby is gorgeous! That being said our room….. the bathroom was falling apart. Our room felt like a cheap motel. The staff was extremely nice and helpful. The location is perfect."
Reviewed on 4 Oct 2025

Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €110 per night from 4 Nov to 5 Nov
€110
4 Nov - 5 Nov
includes taxes & fees
7.8/10 Good! (2,417 reviews)
Good for 3 nights
"The price was right, the location excellent for shopping, riverwalk, other attractions within walking distance. The rooms are tiny, the bar and breakfast inconsistent. The mattress was terrible and needs to be replaced. The lobby area is beautifully refurbished and a place to spend time reading, ..."
Reviewed on 30 Sept 2025

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €169 per night from 5 Nov to 6 Nov
€169
5 Nov - 6 Nov
includes taxes & fees
8.4/10 Very Good! (5,020 reviews)
"Hotel is great and they were very attentive to anything that was needed. I cant say enough about the staff. Chicago is one of this country's great walkable cities so the location provided great opportunity to easier get where you want to go."
Reviewed on 1 Oct 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
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

Skydeck - Willis Tower Admission
€38
per adult
100% of travellers recommend

Chicago By Night River & Lake Cruise
€38
per adult
96% of travellers recommend

Chicago Sightseeing River and Lake Cruise
€38
per adult
100% of travellers recommend
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Packages
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