Search Cheap Flights to
Winfield

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Winfield Flights as Low as $108

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

Frontier Airlines
Frontier Airlines
United
American Airlines
United
Frontier Airlines
Delta
Delta
Frontier Airlines
Sun Country Airlines
United
Frontier Airlines
Delta
JetBlue Airways
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 September, 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 $108, 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 $108 right now, why wait?

Winfield Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$108

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! (2,676 reviews)
"It’s our go-to place near the O’Hare Airport. Clean, safe, great amenities and friendly staff. I like the newly renovated rooms, too. No complaints!"

Reviewed on Jun 19, 2026

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
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! (2,306 reviews)
"Always a great place to stay the night before an early international flight out of ORD. Staff at the front desk, restaurants, and cafe are all extremely friendly and helpful. At the Gaslight Club (old-style restaurant and piano bar), my friend said, "This is the best duck dish I have EVER had!""

Reviewed on Jun 19, 2026

Hilton Chicago O'Hare Airport
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! (1,267 reviews)
"The pool is great and the restaurant was convenient and price was appropriate."

Reviewed on Jun 19, 2026

Marriott Chicago O'Hare
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! (2,991 reviews)
"Great experience! Great choice"

Reviewed on Jun 19, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG
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! (2,811 reviews)
"Clean rooms"

Reviewed on Jun 19, 2026

SureStay Plus Hotel by Best Western Chicago Lombard
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! (1,001 reviews)
"Very spacious room and an excellent stay. Each suite has its own living room separate from an oversized bedroom while there are big screen tvs in each. Perfect for travelers who need space to spread out, relax, unwind. Airport shuttle was super convenient, and to top it all off the workout room was ..."

Reviewed on Jun 19, 2026

Sheraton Suites Chicago O'Hare
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

4 out of 5
1200 N Mittel Blvd Wood Dale IL
Book a stay at this business-friendly hotel in Wood Dale. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
7.8/10 Good! (1,001 reviews)
"Staff was friendly and the room was really clean"

Reviewed on Jun 19, 2026

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
Super 8 by Wyndham Chicago O'Hare Airport

Super 8 by Wyndham Chicago O'Hare Airport

3.5 out of 5
2951 Touhy Ave Elk Grove Village IL
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
7.6/10 Good! (1,713 reviews)
"El traslado del aeropuerto hacía el hotel es complicado, se tandan en llegar. El desayuno muy pobre, sin proteina y el lugar para desayunar demasiado pequeño para la cantidad de huespedes."

Reviewed on Jun 19, 2026

Super 8 by Wyndham Chicago O'Hare Airport
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.