$144 Cheap Flights from Greensboro (GSO) to Chicago (MDW)

View $144 flight on Mon, Jan 12, 2026Opens in a new window

Popular airlines from Piedmont Triad Intl. Airport (GSO) to Chicago Midway Airport (MDW)

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Cheap Flights from Greensboro to Chicago (GSO-MDW)

Prices were available within the past 7 days and start at $144 for one-way flights and $219 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, May 20 - Sat, May 30
GSO
Greensboro
MDW
Chicago
$219 Roundtrip, found 10 hours ago
$219
Roundtrip
found 10 hours ago
Select Delta flight, departing Wed, May 20 from Greensboro to Chicago, returning Sat, May 30, priced at $219 found 10 hours ago
Delta
Wed, Jan 21 - Sun, Jan 25
GSO
Greensboro
MDW
Chicago
$224 Roundtrip, found 5 hours ago
$224
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Jan 21 from Greensboro to Chicago, returning Sun, Jan 25, priced at $224 found 5 hours ago
Delta
Thu, Apr 9 - Mon, Apr 13
GSO
Greensboro
MDW
Chicago
$229 Roundtrip, found 2 hours ago
$229
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, Apr 9 from Greensboro to Chicago, returning Mon, Apr 13, priced at $229 found 2 hours ago
Delta
Wed, Jan 21 - Sun, Jan 25
GSO
Greensboro
MDW
Chicago
$234 Roundtrip, found 6 days ago
$234
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 21 from Greensboro to Chicago, returning Sun, Jan 25, priced at $234 found 6 days ago
Delta
Tue, Mar 10 - Sat, Mar 14
GSO
Greensboro
MDW
Chicago
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Mar 10 from Greensboro to Chicago, returning Sat, Mar 14, priced at $249 found 1 day ago
Delta
Wed, May 20 - Mon, Jun 1
GSO
Greensboro
MDW
Chicago
$250 Roundtrip, found 10 hours ago
$250
Roundtrip
found 10 hours ago
Select Delta flight, departing Wed, May 20 from Greensboro to Chicago, returning Mon, Jun 1, priced at $250 found 10 hours ago
Delta
Fri, Jan 2 - Wed, Jan 14
GSO
Greensboro
MDW
Chicago
$253 Roundtrip, found 10 hours ago
$253
Roundtrip
found 10 hours ago
Select Delta flight, departing Fri, Jan 2 from Greensboro to Chicago, returning Wed, Jan 14, priced at $253 found 10 hours ago
Delta
Thu, Mar 12 - Sat, Mar 14
GSO
Greensboro
MDW
Chicago
$254 Roundtrip, found 1 day ago
$254
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Mar 12 from Greensboro to Chicago, returning Sat, Mar 14, priced at $254 found 1 day ago
Delta
Sun, May 24 - Mon, Jun 1
GSO
Greensboro
MDW
Chicago
$255 Roundtrip, found 10 hours ago
$255
Roundtrip
found 10 hours ago
Select Delta flight, departing Sun, May 24 from Greensboro to Chicago, returning Mon, Jun 1, priced at $255 found 10 hours ago
Delta
Fri, Jan 2 - Mon, Jan 19
GSO
Greensboro
MDW
Chicago
$258 Roundtrip, found 10 hours ago
$258
Roundtrip
found 10 hours ago
Select Delta flight, departing Fri, Jan 2 from Greensboro to Chicago, returning Mon, Jan 19, priced at $258 found 10 hours ago

Find the cheapest month to fly from Greensboro (GSO) to Chicago (MDW)

February is typically the cheapest month to fly

From $216 - $619 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $389
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $389
Flights from Greensboro (GSO) to Chicago (MDW)
Origin airport
Piedmont Triad Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$218
Distance
573 mi

Greensboro to Chicago Flights

The cheapest times to fly from Greensboro to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Greensboro to Chicago are during the month of May. You can find some of the cheapest flights from Greensboro to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Greensboro to Chicago

Sunday is one of the best days to book for cheap flights from Greensboro to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Greensboro to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Greensboro to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $144 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Greensboro to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Greensboro to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Piedmont Triad Intl. Airport (GSO) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $144 or cheap return flight from $219 from Piedmont Triad Intl. Airport (GSO) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Piedmont Triad Intl. Airport (GSO) to Midway Intl. Airport (MDW)?
The cheapest month to fly from GSO to MDW is May, when there's less demand. Off-peak months are usually when airlines offer better prices between these airports.
What is the cheapest airline that flies from Piedmont Triad Intl. Airport (GSO) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest GSO to MDW flight.
How many flights per day from Piedmont Triad Intl. Airport (GSO) to Midway Intl. Airport (MDW)?
There aren't any daily direct flights departing from Piedmont Triad Intl. Airport (GSO) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from GSO to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Piedmont Triad Intl. Airport (GSO) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) on schedule, select a flight that leaves Piedmont Triad Intl. Airport (GSO) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Piedmont Triad Intl. Airport (GSO)?
Explore your flight options from Piedmont Triad Intl. Airport (GSO) to O'Hare Intl. Airport (ORD). This is the only airport in Chicago you can arrive at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Piedmont Triad Intl. Airport (GSO) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from GSO to MDW shortly before your journey is generally more expensive. But if you're flexible with your departure times and dates, you could land a cheap last-minute fare.
Is it cheaper to book a GSO to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a GSO to MDW flight and hotel package with Expedia could lead to significant savings. Better yet, having it all in one place will take the hassle out of planning your trip. Just secure your flights and choose from our wide range of stays, then personalize your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Piedmont Triad Intl. Airport (GSO) to Midway Intl. Airport (MDW)?
Usually, it's possible to reschedule or cancel your GSO to MDW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more details on our Customer Service portal.

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*Available to One Key members.