Winfield Vacations from $586
Book a Hotel + Flight or Car together to unlock savings
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.
Four Seasons Hotel Chicago
Downtown Chicago
$1,169
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Perfect location for shopping, beach, and restaurants. Very clean and staff is very friendly… did not disappoint. Everything met the mark and expectations of a Four Seasons.
Reviewed on Sep 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$969
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!
Reviewed on Sep 2, 2026
Stay near popular Winfield attractions
Royal Golf Club at Klein Creek
This challenging 18-hole championship course features rolling prairieland and strategic water hazards. Enjoy the cozy clubhouse and Americana cuisine after tackling the notorious 9th hole, one of Chicago's toughest par 4s.
What to do in Winfield
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Winfield Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$264 nightly
$310 total
Sep 27 - Sep 28
Total with taxes and fees
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$179 nightly
$204 total
Sep 7 - Sep 8
Total with taxes and fees
9/10 Wonderful! (3,103 reviews)
"The staff were very helpful. I highly recommend the mango salmon at the their restaurant. I had a concern with my parking and the staff took care of me. This was my second visit and will return."
Reviewed on Sep 2, 2026
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
$67 nightly
$74 total
Sep 20 - Sep 21
Total with taxes and fees
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 |
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Frequently asked questions
How much does a Winfield vacation package cost?
You'll find cheap prices from $586 on Expedia for your Winfield getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Winfield costs.
What are the cheapest months to go to Winfield?
If you're looking to book a cheap Winfield vacation package, consider planning a trip in December, January and February. You'll usually find better prices on hotels and airfares during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Winfield?
Usually, a handful of days is enough to explore the main attractions during your Winfield vacation. But if you'd like to have some time to rest or take day trips, think about extending your itinerary.
How to find the best Winfield package deals?
Start your search for a Winfield package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Winfield package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winfield adventure underway.
Is it cheaper to book a Winfield vacation as a package?
You can enjoy significant savings on your next Winfield break by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winfield?
Score amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Winfield break.
Does Expedia offer Book Now, Pay Later Winfield vacation packages?
Set off on your dream getaway to Winfield with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or hold off until payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.