Winfield Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Winfield Vacation Packages

Winfield Hotel Deals

Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is ₩209,535 per night from Jul 13 to Jul 14
₩209,535
₩238,828 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (1,718 reviews)
"Clean, worth the price"

Reviewed on Jul 11, 2025

Hyatt Regency O'Hare Chicago
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩246,856 per night from Aug 8 to Aug 9
₩246,856
₩289,785 total
Aug 8 - Aug 9
includes taxes & fees
8/10 Very Good! (2,069 reviews)
"Super convenient for an early morning flight, and surprisingly quiet considering it’s only steps from the terminal."

Reviewed on Jul 10, 2025

Hilton Chicago O'Hare Airport
Marriott Chicago O'Hare
Marriott Chicago O'Hare
3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩221,860 per night from Jul 26 to Jul 27
₩221,860
₩260,442 total
Jul 26 - Jul 27
includes taxes & fees
8.4/10 Very Good! (1,080 reviews)
"For the price we paid, i was disappointed to find that our room smelt like cigarettes. A few fixtures in the room seem to be stained from smoke and the carpet didn’t feel clean. But aside from that, the pool was clean, bathroom was nice, breakfast was expensive but it was okay. Stayed for two days. ..."

Reviewed on Jul 11, 2025

Marriott Chicago O'Hare
See all 1,287 properties in Winfield
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 featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

4.5/5(3,318 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Frequently asked questions

How much does a Winfield vacation package cost?
You'll find cheap prices 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?
Travel in the off-season and you're likely to find cheap Winfield vacation packages. Bear in mind that public holidays and local events and festivals can impact prices, so do a little research before booking.
How many days is enough for Winfield?
The ideal length for your Winfield vacation depends on what you'd like to see. Usually, a few days to a week will give you time to hit all the main attractions and explore some hidden treasures along the way.
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.
How to plan a trip to Winfield?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Winfield.
  2. Set a budget: Factor in costs like flights, transportation and food when working out how much to set aside for your trip to Winfield. Then, select a property that suits your budget, whether that's an economical stay or a high-end retreat.
  3. Determine how many days away: Start by making a list of all the attractions you'd like to experience in Winfield. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Winfield vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.