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Winfield

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Winfield Flights as Low as $108

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

Frontier Airlines
Mon, Sep 28 - Mon, Oct 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$108 Roundtrip, found 20 hours ago
$108
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Oct 5, priced at $108 found 20 hours ago
Frontier Airlines
Tue, Sep 22 - Tue, Oct 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Oct 6, priced at $108 found 2 days ago
United
Tue, Jul 21 - Tue, Aug 11
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 2 days ago
$109
Roundtrip
found 2 days ago
Select United flight, departing Tue, Jul 21 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $109 found 2 days ago
American Airlines
Tue, Jul 21 - Tue, Aug 11
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 2 days ago
$109
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jul 21 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $109 found 2 days ago
United
Wed, Jul 29 - Tue, Aug 18
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 2 days ago
$112
Roundtrip
found 2 days ago
Select United flight, departing Wed, Jul 29 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, Aug 18, priced at $112 found 2 days ago
Frontier Airlines
Mon, Sep 14 - Mon, Sep 14
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$113 Roundtrip, found 4 hours ago
$113
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Sep 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Sep 14, priced at $113 found 4 hours ago
Delta
Tue, Aug 18 - Wed, Aug 19
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Aug 18 from Minneapolis - St. Paul Intl. to Midway Intl., returning Wed, Aug 19, priced at $117 found 2 days ago
Delta
Wed, Nov 11 - Wed, Nov 11
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 23 hours ago
$117
Roundtrip
found 23 hours ago
Select Delta flight, departing Wed, Nov 11 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $117 found 23 hours ago
Frontier Airlines
Tue, Aug 25 - Wed, Sep 9
MCO
Orlando Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 4 days ago
$135
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Orlando Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $135 found 4 days ago
Sun Country Airlines
Fri, Nov 13 - Sun, Nov 15
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 18 hours ago
$167
Roundtrip
found 18 hours ago
Select Sun Country Airlines flight, departing Fri, Nov 13 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Sun, Nov 15, priced at $167 found 18 hours ago
United
Wed, Aug 19 - Thu, Aug 20
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 19 from Newark Liberty Intl. Airport to O'Hare Intl., returning Thu, Aug 20, priced at $195 found 1 day ago
Frontier Airlines
Tue, Sep 15 - Tue, Sep 22
MCO
Orlando Intl.
MDW
Midway Intl.
$210 Roundtrip, found 3 days ago
$210
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Sep 15 from Orlando Intl. to Midway Intl., returning Tue, Sep 22, priced at $210 found 3 days ago
Delta
Tue, Oct 6 - Sat, Oct 10
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$223 Roundtrip, found 4 days ago
$223
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Oct 6 from Newark Liberty Intl. Airport to Midway Intl., returning Sat, Oct 10, priced at $223 found 4 days ago
JetBlue Airways
Wed, Aug 19 - Tue, Sep 8
MCO
Orlando Intl.
ORD
O'Hare Intl.
$269 Roundtrip, found 5 days ago
$269
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, Aug 19 from Orlando Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $269 found 5 days ago
American Airlines
Wed, Jul 1 - Sat, Jul 4
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$311 Roundtrip, found 4 days ago
$311
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 1 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sat, Jul 4, priced at $311 found 4 days ago
American Airlines
Thu, Jul 30 - Sat, Aug 8
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$451 Roundtrip, found 17 hours ago
$451
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Thu, Jul 30 from Newark Liberty Intl. Airport to Greater Rockford, returning Sat, Aug 8, priced at $451 found 17 hours ago

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

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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

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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

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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

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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

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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

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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

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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

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Super 8 by Wyndham Chicago O'Hare Airport
See all 1,400 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.