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Winfield

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Winfield Flights as Low as $118

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

Frontier Airlines
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American Airlines
American Airlines
Frontier 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 August, 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 15 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 $118, 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 $118 right now, why wait?

Winfield Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$137

Last Minute Hotel Deals in Winfield

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! (2,613 reviews)
"I thoroughly appreciated the hospitality and the house keeper was very nice."

Reviewed on Jun 4, 2026

Hyatt Regency O'Hare Chicago
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! (2,994 reviews)
"Room was clean so was the bathroom. They don’t however give any free water. Even 500ml water bottle there is pricey. Overall service and cleanliness was top notch."

Reviewed on Jun 3, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG
Sheraton Suites Chicago O'Hare

Sheraton Suites Chicago O'Hare

3.5 out of 5
6501 N Mannheim Rd Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the helpful ...
9/10 Wonderful! (1,011 reviews)
"Close to the airport, easy to visit downtown Chicago by train (blue line). Great staff, clean room and great breakfast."

Reviewed on Jun 3, 2026

Sheraton Suites Chicago O'Hare
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! (2,315 reviews)
"Always a pleasure to spend a night here before an early flight."

Reviewed on Jun 4, 2026

Hilton Chicago O'Hare Airport
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (2,773 reviews)
"Had a great stay the room was nice and clean"

Reviewed on Jun 4, 2026

SureStay Plus Hotel by Best Western Chicago Lombard
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! (1,256 reviews)
"The room was clean, never had a problem with grabbing towels or rags, the food from the bar was really good and staff was nice and pleasant."

Reviewed on Jun 2, 2026

Marriott Chicago O'Hare
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 (1,131 reviews)
"Good location next to Target and plenty of restaurants in the area. Good parking."

Reviewed on Jun 1, 2026

Red Roof Inn PLUS+ Chicago - Willowbrook
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
707 E Butterfield Road Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (1,610 reviews)
"Very good"

Reviewed on Jun 3, 2026

Embassy Suites by Hilton Chicago Lombard Oak Brook
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.