Winfield Vacations from $142
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 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
Your Winfield Vacation
When you organize a vacation package to Winfield, you can relax and enjoy your escape knowing your travel plans have been worked out ahead of time. Uncover the many charms of this amazing city from your base in a neighborhood like Medinah, which is great for golfing. Fill your itinerary with tours of Wheaton College, College of Dupage and North Central College Fine & Performing Arts, some of the attractions you just have to see during a trip to Winfield. Expedia has what you need to escape your daily routine. Tailor your vacation to Winfield to suit your travel style, whatever that may be!
The Latest Winfield vacation packages
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $278, price is now $142 per person
$142
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,413, price is now $729 per person
$729
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Clean, quiet and comfortable room, courteous staff. We received a $25k food credit through Expedia and got exceptional pastries and coffee at the adjacent cafe.
Reviewed on Nov 22, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $320, price is now $167 per person
$167
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Really great spot in the city right in the middle like a five minute walk to to everything around you the staff was great. The rooms were beautiful.
Reviewed on Nov 24, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,292, price is now $680 per person
$680
per person
Dec 27 - Jan 2
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world.
Reviewed on Nov 25, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $552, price is now $312 per person
$312
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Great stay. Excellent location.
Reviewed on Nov 23, 2025
Discover the most popular places to visit in Winfield
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy 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 Winfield
Skydeck - Willis Tower Admission
$44
per adult
96% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
Winfield Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$196 nightly
The price is $230 total per night from Dec 19 to Dec 20
$230 total
Dec 19 - Dec 20
Total with taxes and 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 Nov 22, 2025
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
$127 nightly
The price is $144 total per night from Nov 30 to Dec 1
$144 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (2,149 reviews)
The room was clean and comfortable. Breakfast was amazing!
Reviewed on Nov 24, 2025
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
$111 nightly
The price is $127 total per night from Dec 15 to Dec 16
$127 total
Dec 15 - Dec 16
Total with taxes and fees
8.6/10 Excellent! (2,631 reviews)
The hotel was great—perfect location, very quiet rooms, and everything was clean. The beds were comfortable, and the room was spacious. The only thing missing was a microwave, which would have been nice to have.
Reviewed on Nov 18, 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.
Find the Best Winfield Vacation Packages
Winfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 9,700 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | DuPage Childrens Museum, Lynfred Winery and Pirates Cove Childrens Theme Park |
More vacations you might like
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
