$67 Cheap Flights from Chicago (MDW) to Greenville (GSP)

View $67 flight on Tue, Dec 9, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP)

Cheap Flights from Chicago to Greenville (MDW-GSP)

Prices were available within the past 7 days and start at $67 for one-way flights and $133 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Dec 9 - Tue, Jan 6
MDW
Chicago
GSP
Greenville
$133 Roundtrip, found 3 days ago
$133
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Dec 9 from Chicago to Greenville, returning Tue, Jan 6, priced at $133 found 3 days ago
Southwest Airlines
Tue, Dec 9 - Tue, Jan 6
MDW
Chicago
GSP
Greenville
$138 Roundtrip, found 3 days ago
$138
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Dec 9 from Chicago to Greenville, returning Tue, Jan 6, priced at $138 found 3 days ago
Southwest Airlines
Tue, Dec 9 - Tue, Jan 6
MDW
Chicago
GSP
Greenville
$150 Roundtrip, found 3 days ago
$150
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Dec 9 from Chicago to Greenville, returning Tue, Jan 6, priced at $150 found 3 days ago
Southwest Airlines
Tue, Nov 4 - Wed, Nov 12
MDW
Chicago
GSP
Greenville
$153 Roundtrip, found 4 days ago
$153
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Chicago to Greenville, returning Wed, Nov 12, priced at $153 found 4 days ago
Southwest Airlines
Sat, Nov 8 - Tue, Nov 11
MDW
Chicago
GSP
Greenville
$155 Roundtrip, found 3 days ago
$155
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Nov 8 from Chicago to Greenville, returning Tue, Nov 11, priced at $155 found 3 days ago
Southwest Airlines
Tue, Nov 4 - Wed, Nov 12
MDW
Chicago
GSP
Greenville
$158 Roundtrip, found 4 days ago
$158
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Chicago to Greenville, returning Wed, Nov 12, priced at $158 found 4 days ago
Southwest Airlines
Sat, Nov 8 - Tue, Nov 11
MDW
Chicago
GSP
Greenville
$160 Roundtrip, found 3 days ago
$160
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Nov 8 from Chicago to Greenville, returning Tue, Nov 11, priced at $160 found 3 days ago
Southwest Airlines
Wed, Oct 8 - Wed, Oct 15
MDW
Chicago
GSP
Greenville
$165 Roundtrip, found 3 days ago
$165
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 8 from Chicago to Greenville, returning Wed, Oct 15, priced at $165 found 3 days ago
Southwest Airlines
Tue, Dec 9 - Tue, Jan 6
MDW
Chicago
GSP
Greenville
$168 Roundtrip, found 3 days ago
$168
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Dec 9 from Chicago to Greenville, returning Tue, Jan 6, priced at $168 found 3 days ago
Delta
Sat, Nov 1 - Thu, Nov 13
MDW
Chicago
GSP
Greenville
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Nov 1 from Chicago to Greenville, returning Thu, Nov 13, priced at $197 found 4 days ago

Find the cheapest month to fly from Chicago (MDW) to Greenville (GSP)

September is typically the cheapest month to fly

From $186 - $648 per traveler.

Alternative airports near Greenville

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

Select flight to Greenville-Spartanburg Intl. GSP. Cheapest option available. Average driving time to city center is 18 minutes. Flights from $264
GSP
Greenville-Spartanburg Intl.
Cheapest
Average driving time to city center18 min
Flights from $264
Flights from Chicago (MDW) to Greenville (GSP)
Origin airport
Midway Intl.
Destination airport
Greenville-Spartanburg Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$132
Distance
562 mi

Chicago to Greenville Flights

The cheapest times to fly from Chicago to Greenville

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 Chicago to Greenville are during the month of December. You can find some of the cheapest flights from Chicago to Greenville with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Greenville

Sunday is one of the best days to book for cheap flights from Chicago to Greenville: 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 Chicago to Greenville

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 Chicago to Greenville in 2025. You can also book with separate airlines for your outbound and return journeys, from $67 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 Chicago to Greenville 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 Chicago to Greenville 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 Midway Intl. Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP) cost?
Secure a cheap one-way flight from $67 or cheap return flight from $133 from Midway Intl. Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP) 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 Midway Intl. Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP)?
December is the most affordable month to fly from MDW to GSP. Planning your trip for the off-season is often the key to finding better fares.
Which airlines fly direct from Midway Intl. Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP)?
Although Chicago, IL (MDW-Midway Intl.) doesn't have any direct flights to Greenville-Spartanburg Intl. Airport (GSP), other airports have nonstop routes. Departing from O'Hare Intl. Airport (ORD) will get you to Greenville without any layovers.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP)?
To find the cheapest airline flying from MDW to GSP, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Midway Intl. Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP)?
You'll have to book a flight with a layover if you're traveling from Midway Intl. Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from MDW to GSP?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Just remember that flight schedules can change depending on a number of factors, including the season and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP) route, aim to travel before 3 PM. Departures after this time have a 22% higher chance of being canceled.**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.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP) last-minute?
Holding off until right before your break to book a ticket from MDW to GSP generally means paying more. While you might find some last-minute discounts, they're not always guaranteed. Be flexible with your travel plans to boost your chances of landing a bargain.
Is it cheaper to book a MDW to GSP flight and hotel package?
You can save money by booking a MDW to GSP flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've chosen your ideal accommodations and flights, consider adding extras such as car rentals, activities and tours.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Greenville-Spartanburg Intl. Airport (GSP)?
You can usually cancel or reschedule your MDW to GSP flight. However, if it's been more than 24 hours since booking, additional charges may apply. Check 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.

Explore a world of travel with Expedia

*Available to One Key members.