Winfield Vacations from ₩444,357
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Winfield Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was ₩606,595, price is now ₩444,357 per person
₩444,357
per person
Feb 2 - Feb 4
found 10 hours ago
Roundtrip flight included
Houston (IAH) 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 Nov 18, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,001,600, price is now ₩673,862 per person
₩673,862
per person
Feb 2 - Feb 4
found 10 hours ago
Roundtrip flight included
Houston (IAH) 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 Nov 17, 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,018,777, price is now ₩726,103 per person
₩726,103
per person
Feb 2 - Feb 4
found 10 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
19.2/10 Exceptional! (1,000 reviews)
Stay was amazing!!! The staff was so friendly, kind, and thoughtful! The rooms were soooo beyond perfect and lovely! And the food at the restaurant was amazing.. especially breakfast! You won’t regret staying here!!!
Reviewed on Nov 18, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ₩665,744, price is now ₩475,814 per person
₩475,814
per person
Feb 2 - Feb 4
found 10 hours ago
Roundtrip flight included
Houston (IAH) 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 Oct 28, 2025
The Emily Hotel
Downtown Chicago
Price was ₩728,918, price is now ₩537,153 per person
₩537,153
per person
Feb 2 - Feb 4
found 10 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special
Reviewed on Nov 11, 2025
Find the Best Winfield Vacation Packages
Winfield Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩286,376 per night from Dec 19 to Dec 20
₩286,376
₩336,177 total
Dec 19 - Dec 20
includes taxes & fees
8.2/10 Very Good! (2,163 reviews)
Clean and quiet and comfortable
Reviewed on Nov 14, 2025
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ₩203,114 per night from Dec 17 to Dec 18
₩203,114
₩231,506 total
Dec 17 - Dec 18
includes taxes & fees
8.6/10 Excellent! (2,128 reviews)
Friendly staff. Quick check-in
Reviewed on Nov 17, 2025
Holiday Inn Chicago O'Hare – Rosemont by IHG
6600 Mannheim Road, building 2 Rosemont IL
Fully refundable
The price is ₩163,856 per night from Nov 27 to Nov 28
₩163,856
₩189,323 total
Nov 27 - Nov 28
includes taxes & fees
8.8/10 Excellent! (2,599 reviews)
Staff was friendly, helpful and efficient. Room was clean, comfortable.
Reviewed on Nov 16, 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.
Discover the most popular places to visit in Winfield
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Grant Park
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
