Winfield Holidays
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Top Flight + Hotel Deals in Winfield
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €906, price is now €617 per person
€617
per person
1 Feb - 6 Feb
found 24 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city
Reviewed on 26 Nov 2025
Chicago luxury home suites
Downtown Chicago
Price was €2,929, price is now €2,019 per person
€2,019
per person
1 Feb - 6 Feb
found 24 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.
Reviewed on 26 Nov 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,714, price is now €1,215 per person
€1,215
per person
1 Feb - 6 Feb
found 24 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Mostly great. The pull out sofa bed is not usable as it’s so uncomfortable. So then they charge $50/night for each rollaway. Thats not a good solution.
Reviewed on 28 Nov 2025
Pendry Chicago
Downtown Chicago
Price was €892, price is now €654 per person
€654
per person
1 Feb - 6 Feb
found 24 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
I had an amazing stay at The Pendry Chicago. The hotel is gorgeous, modern, and feels truly high-end without trying too hard. My room was super clean, comfortable, and quiet—honestly one of the best sleep setups I’ve had in a hotel.
The staff made the whole experience even better. Everyone I talked to was friendly, helpful, and actually seemed to enjoy their jobs. The lobby bar and restaurant were great too, and the whole vibe of the place is relaxed but still upscale.
The location made it easy to get around the city, but I kept finding myself wanting to head back early just to enjoy the hotel.
I’d definitely stay here again and recommend it to anyone visiting Chicago.
Reviewed on 30 Nov 2025
Top hotels in Winfield
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is €198 per night from 26 Dec to 27 Dec
€198
26 Dec - 27 Dec
includes taxes & fees
8.2/10 Very Good! (2,175 reviews)
Room was great. Very disappointed with the management. I was told the bill would be refunded fora mixup on the date. The front desk girl on Sunday night went into the office to consult the mgr. she came back and stated the Mgr will be reimbursing Hotels.com forth night of the15th. Hotels.com informed ...
Reviewed on 22 Nov 2025
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is €124 per night from 10 Dec to 11 Dec
€124
10 Dec - 11 Dec
includes taxes & fees
8.6/10 Excellent! (2,156 reviews)
Airport shuttle was great. Very quick to get to/from the hotel to ORD. Staff were very accommodating.
Reviewed on 25 Nov 2025
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
The price is €109 per night from 15 Dec to 16 Dec
€109
15 Dec - 16 Dec
includes taxes & fees
8.6/10 Excellent! (2,639 reviews)
The room was nice, the staff was pleasant, attentive, and helpful. As a handicapped person the hotel has plenty of ramps.
Reviewed on 26 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
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.
Wrigley Field
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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 Winfield
Skydeck - Willis Tower Admission
€38
per adult
96% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
84% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
€39
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
