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Winfield

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Winfield Flights as Low as $56

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
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United
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Delta
Delta
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American Airlines
American Airlines
American Airlines

Cheap Flights to Winfield

Fall in love at first flight with your vacation to Winfield by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winfield on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winfield, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Winfield

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winfield with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Winfield?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winfield are in April, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winfield?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Winfield.

What airport is best to fly into Winfield?

When you’re planning your trip to Winfield, convenience is the name of the game. Luckily, Winfield Dupage Airport is nearby so you can deplane and get going on checking off everything on your Winfield must-do list.

How much are flights to Winfield?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winfield on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $56, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Winfield?

The trick to saving a stack of cash on your flight to Winfield? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $56 right now, why wait?

Winfield Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$56

Last Minute Hotel Deals in Winfield

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,238 reviews)
Yyy

Reviewed on Mar 24, 2026

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,433 reviews)
Dddd

Reviewed on Mar 25, 2026

Hyatt Regency O'Hare Chicago
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
8.6/10 Excellent! (1,234 reviews)
It was all good!

Reviewed on Mar 23, 2026

Marriott Chicago O'Hare
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
7.2/10 Good! (1,487 reviews)
The style of the room was perfect for us since my sister likes to sleep with the TV on, and I like to sleep in dark and silence.the The 2 sections of the room was just right. We would have liked to have had some paper plates and plastic ware in the cabinet for us to microwave some of our restaurant ...

Reviewed on Mar 25, 2026

Chicago Club Inn & Suites
Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport

3 out of 5
6810 Mannheim Rd Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8.4/10 Very Good! (3,316 reviews)
Great Hotel to stay, minor issue with A/C, but over all the staff and facilities were fantastic. Hopped on the shuttle to the airport in a quick second.

Reviewed on Mar 23, 2026

Hyatt Place Chicago/O'Hare Airport
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
6600 Mannheim Road, building 2 Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
9/10 Wonderful! (2,881 reviews)
Clean and comfortable. Very convenient to the airport.

Reviewed on Mar 24, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2 out of 5
4021 North Mannheim Rd Schiller Park IL
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, a free airport shuttle, and a 24-hour fitness center. Our guests praise the helpful ...
8.2/10 Very Good! (2,457 reviews)
Good and comfortable stay

Reviewed on Mar 25, 2026

Sonesta Simply Suites Chicago O'Hare Airport
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway Willowbrook IL
Stay at this hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.4/10 (1,077 reviews)
They accept pets, rooms are gross and full of roaches. Water damage causing leaky ceilings and showers that wont turn off fully leaving the room to be humid. Price is cheap but still too much for the conditions. Youre definitely paying for the area

Reviewed on Mar 22, 2026

Red Roof Inn PLUS+ Chicago - Willowbrook
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.