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 $111

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

Frontier Airlines
Wed, May 28 - Mon, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$111 Roundtrip, found 5 days ago
$111
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, May 28 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Mon, Jun 2, priced at $111 found 5 days ago
Spirit Airlines
Sun, May 18 - Tue, May 20
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$132 Roundtrip, found 23 hours ago
$132
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Sun, May 18 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Tue, May 20, priced at $132 found 23 hours ago
Spirit Airlines
Sun, May 18 - Thu, May 22
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$142 Roundtrip, found 21 hours ago
$142
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Sun, May 18 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, May 22, priced at $142 found 21 hours ago
Frontier Airlines
Fri, May 30 - Mon, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$143 Roundtrip, found 2 days ago
$143
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, May 30 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Mon, Jun 2, priced at $143 found 2 days ago
Frontier Airlines
Wed, May 28 - Fri, May 30
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$145 Roundtrip, found 5 days ago
$145
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, May 28 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Fri, May 30, priced at $145 found 5 days ago
Spirit Airlines
Mon, Jun 2 - Thu, Jun 5
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 1 hour ago
$147
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Mon, Jun 2 from Southwest Florida Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $147 found 1 hour ago
Spirit Airlines
Sun, Jun 1 - Thu, Jun 5
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$150 Roundtrip, found 14 hours ago
$150
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Sun, Jun 1 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, Jun 5, priced at $150 found 14 hours ago
Spirit Airlines
Thu, May 15 - Thu, May 22
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$150 Roundtrip, found 4 days ago
$150
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, May 15 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, May 22, priced at $150 found 4 days ago
Bargain Flight
Thu, May 22 - Sun, May 25
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$168 Roundtrip, found 18 hours ago
$168
Roundtrip
found 18 hours ago
Select Bargain Flight flight, departing Thu, May 22 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sun, May 25, priced at $168 found 18 hours ago
Delta
Sat, Jun 7 - Sat, Jun 7
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$191 Roundtrip, found 23 hours ago
$191
Roundtrip
found 23 hours ago
Select Delta flight, departing Sat, Jun 7 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sat, Jun 7, priced at $191 found 23 hours ago
American Airlines
Sat, Jun 14 - Wed, Jun 18
GSO
Piedmont Triad Intl.
ORD
O'Hare Intl.
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jun 14 from Piedmont Triad Intl. to O'Hare Intl., returning Wed, Jun 18, priced at $203 found 1 day ago
JetBlue Airways
Wed, May 28 - Wed, Jun 4
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$214 Roundtrip, found 5 days ago
$214
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, May 28 from Southwest Florida Intl. to O'Hare Intl., returning Wed, Jun 4, priced at $214 found 5 days ago
Delta
Sat, Jun 21 - Sat, Jun 21
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$215 Roundtrip, found 1 day ago
$215
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jun 21 from Southwest Florida Intl. to Midway Intl., returning Sat, Jun 21, priced at $215 found 1 day ago
Delta
Sun, May 25 - Tue, Jun 3
GSO
Piedmont Triad Intl.
MDW
Midway Intl.
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, May 25 from Piedmont Triad Intl. to Midway Intl., returning Tue, Jun 3, priced at $222 found 1 day ago
Delta
Thu, May 1 - Tue, May 6
HSV
Huntsville Intl.
MDW
Midway Intl.
$311 Roundtrip, found 19 hours ago
$311
Roundtrip
found 19 hours ago
Select Delta flight, departing Thu, May 1 from Huntsville Intl. to Midway Intl., returning Tue, May 6, priced at $311 found 19 hours ago
Alaska Airlines
Mon, Jun 30 - Sun, Jul 6
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$11,654 Roundtrip, found 6 days ago
$11,654
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Mon, Jun 30 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Jul 6, priced at $11,654 found 6 days 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 May, 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 $111, 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 $111 right now, why wait?

Winfield Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$111

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
The price is $173 per night from May 18 to May 19
$173
includes taxes & fees
May 18 - May 19
Book a stay at this eco-certified hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,527 reviews)
"Great classic Hyatt hotel!"

Reviewed on Apr 29, 2025

Hyatt Regency O'Hare Chicago
Marriott Chicago O'Hare
Marriott Chicago O'Hare
3.5 out of 5
8535 West Higgins Road, Chicago, IL
The price is $198 per night from May 23 to May 24
$198
includes taxes & fees
May 23 - May 24
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
8.4/10 Very Good! (1,019 reviews)
"Nice property. Clean."

Reviewed on Apr 25, 2025

Marriott Chicago O'Hare
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
4 out of 5
O'Hare International Airport, Chicago, IL
The price is $253 per night from May 24 to May 25
$253
includes taxes & fees
May 24 - May 25
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8/10 Very Good! (2,033 reviews)
"VERY CONVIENT"

Reviewed on Apr 28, 2025

Hilton Chicago O'Hare Airport
La Quinta by Wyndham Chicago O'Hare Airport
La Quinta by Wyndham Chicago O'Hare Airport
2.5 out of 5
6860 Mannheim Rd, Rosemont, IL
The price is $113 per night from May 12 to May 13
$113
includes taxes & fees
May 12 - May 13
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! (1,376 reviews)
"The hotel was clean and quiet. I had a good night and slept like a baby. I’ve enjoyed the free breakfast buffet as well. Would definitely recommend them"

Reviewed on Apr 28, 2025

La Quinta by Wyndham Chicago O'Hare Airport
The Champagne Lodge & Luxury Suites
The Champagne Lodge & Luxury Suites
3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is $130 per night from May 5 to May 6
$130
includes taxes & fees
May 5 - May 6
Stay at this 3.5-star boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,086 reviews)
"Really love this place great location for getaways and also get to the city"

Reviewed on Apr 28, 2025

The Champagne Lodge & Luxury Suites
Holiday Inn Chicago SW-Countryside ConfCtr by IHG
Holiday Inn Chicago SW-Countryside ConfCtr by IHG
3.5 out of 5
6201 Joliet Rd, Countryside, IL
The price is $97 per night from May 11 to May 12
$97
includes taxes & fees
May 11 - May 12
Stay at this 3.5-star business-friendly hotel in Countryside. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the clean rooms ...
7.6/10 Good! (1,003 reviews)
"Exellent"

Reviewed on Apr 23, 2025

Holiday Inn Chicago SW-Countryside ConfCtr by IHG
Hyatt Place Chicago/O'Hare Airport
Hyatt Place Chicago/O'Hare Airport
3 out of 5
6810 Mannheim Rd, Rosemont, IL
The price is $131 per night from May 19 to May 20
$131
includes taxes & fees
May 19 - May 20
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8.2/10 Very Good! (2,902 reviews)
"This is a nice comforting place to do a get a way. We had a wonderful time."

Reviewed on Apr 27, 2025

Hyatt Place 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
The price is $90 per night from May 1 to May 2
$90
includes taxes & fees
May 1 - May 2
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 ...
8.8/10 Excellent! (2,033 reviews)
"Housekeeping ony after checkout so lots of towels and trash can in hall ways"

Reviewed on Apr 28, 2025

SureStay Plus Hotel by Best Western Chicago Lombard
See all 1,226 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.