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$104+ Cheap flights from Greenville (GSP) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — MDW
Dec 24 — Dec 311
Wed 12/24
Wed 12/31
1 adult, Economy
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Cheap flight deals from Greenville to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Greenville (GSP) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 24, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$213
(Southwest)

One-way from

$135
(Southwest)

Popular in

November

Cheapest in

June

Average price

$633
Provider with most accurate pricing for Greenville-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Greenville-Chicago Midway flights.
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From Greenville to Chicago Midway
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One-way flight from Greenville to Chicago Midway
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Highest demand for flights based on searches. 27% potential increase in price ($127 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Greenville to Midway

Cheapest flights from Greenville to Midway
Explore the most affordable flight options available from Greenville to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 24, 2025.

This Delta deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/87:36 pmGSP - MDW
1 stop5h 11mDelta
Sun 12/146:00 amMDW - GSP
1 stop4h 15mDelta
Deal found 11/22$249
This Southwest deal was found by Cheapflights users on 11/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/144:15 pmGSP - MDW
1 stop8h 55mSouthwest
Tue 1/1310:05 amMDW - GSP
1 stop6h 30mSouthwest
Deal found 11/21$258
This Delta deal was found by Cheapflights users on 11/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:25 amGSP - MDW
1 stop6h 09mDelta
Sat 12/134:29 pmMDW - GSP
1 stop6h 12mDelta
Deal found 11/23$269
This Kiwi.com deal was found by Cheapflights users on 11/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/234:43 pmGSP - MDW
2 stops30h 29mMultiple Airlines
Wed 12/313:10 pmMDW - GSP
1 stop18h 43mMultiple Airlines
Deal found 11/21$274
This Delta deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:25 amGSP - MDW
1 stop6h 09mDelta
Sun 12/76:00 amMDW - GSP
1 stop4h 15mDelta
Deal found 11/22$281
This Kiwi.com deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/83:00 pmGSP - MDW
2 stops18h 46mMultiple Airlines
Sun 12/146:37 pmMDW - GSP
1 stop23h 46mMultiple Airlines
Deal found 11/22$291
This Southwest deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:40 amGSP - MDW
2 stops6h 20mSouthwest
Sun 12/79:35 amMDW - GSP
1 stop11h 00mSouthwest
Deal found 11/22$292
This Delta deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/247:27 amGSP - MDW
1 stop6h 07mDelta
Fri 11/285:34 pmMDW - GSP
1 stop5h 11mDelta
Deal found 11/22$299
This Delta deal was found by Cheapflights users on 11/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:45 amGSP - MDW
1 stop4h 09mDelta
Tue 12/95:29 pmMDW - GSP
1 stop5h 11mDelta
Deal found 11/23$304
This Southwest deal was found by Cheapflights users on 11/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:35 amGSP - MDW
2 stops7h 00mSouthwest
Tue 12/912:55 pmMDW - GSP
1 stop5h 45mSouthwest
Deal found 11/23$309

Cheapflights Fare Finder

 
Customize your flight search to find flights from Greenville to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 24, 2025.
Use the filters below to find and compare flights from Greenville to Chicago Midway Airport that are best for you.

Fly from

Greenville

Fly to

Midway

Route

Depart

Return

Price

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 1/22

10:05 am-2:55 pm

1 stop5h 50m

Chicago Midway

Tue 1/27

10:05 am-5:35 pm

1 stop6h 30m

$213

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 2/20

7:40 pm-10:42 pm

1 stop4h 02m

Chicago Midway

Tue 2/24

6:00 am-11:08 am

1 stop4h 08m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 1/20

7:20 am-12:51 pm

1 stop6h 31m

Chicago Midway

Sat 1/24

1:26 pm-6:04 pm

1 stop3h 38m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 1/20

10:05 am-2:55 pm

1 stop5h 50m

Chicago Midway

Sat 1/24

12:15 pm-7:50 pm

1 stop6h 35m

$228

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 1/31

7:20 am-12:46 pm

1 stop6h 26m

Chicago Midway

Sun 2/1

6:00 am-11:03 am

1 stop4h 03m

$247

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 1/30

7:20 am-12:46 pm

1 stop6h 26m

Chicago Midway

Sun 2/1

6:00 am-11:03 am

1 stop4h 03m

$254

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sun 12/14

4:15 pm-9:50 pm

1 stop6h 35m

Chicago Midway

Tue 1/13

9:55 am-7:50 pm

2 stops8h 55m

$263

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 1/10

10:50 am-1:40 pm

1 stop3h 50m

Chicago Midway

Sun 1/11

1:35 pm-8:20 pm

2 stops5h 45m

$264

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 12/17

7:40 am-4:00 pm

2 stops9h 20m

$104

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 3/12

7:15 am-12:35 pm

1 stop6h 20m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/23

Showing 1-10 of 14 results
1
2

Compare providers for flights from Greenville to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Greenville to Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Greenville-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Greenville-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Greenville-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Greenville-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Greenville-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Greenville to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Greenville with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Greenville to Chicago Midway Airport

What is the cheapest month to book a flight from Greenville to Chicago Midway Airport?

Currently, August is the cheapest month in which you can book a flight from Greenville to Chicago Midway Airport (average of $58). Flying from Greenville to Chicago Midway Airport in December is currently the most expensive (average of $190). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated November 24, 2025.
Read through reviews of airlines operating flights from Greenville to Chicago Midway Airport, such as Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,997 reviews

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
7,997 reviews
Delta
7.9
Good
7,997 reviews

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Greenville to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Greenville to Chicago Midway?

    For a flight from Greenville to Chicago Midway, you will be flying from Greenville. Greenville (GSP) is just 10.4 mi from the center of the city. Greenville is the only Greenville airport and it handles 0 outbound flights to Chicago Midway per day. 1 airline has flights to Chicago Midway from Greenville on a regular basis.

  • How long is the flight from Greenville to Chicago Midway Airport?

    For as low as $211, Southwest can have you in Chicago Midway Airport from Greenville in 3h 50m. The distance between Greenville and Chicago Midway Airport is about 562 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Greenville to Chicago Midway Airport round-trip?

    Flying on Delta is currently your cheapest option to Chicago Midway Airport, with prices starting at $180. This flight start at 45% lower than the current average price 3 months from now.

  • Can I find deals for flights from Greenville to Midway that include hotel bookings?

    Yes. In addition to deals on Greenville to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Greenville to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Greenville to Midway.

  • Can I find deals for business class flights from Greenville to Midway?

    Yes. Cheapflights offers flight deals from Greenville to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Greenville to Chicago Midway Airport?

    Currently, August is the cheapest month in which you can book a flight from Greenville to Chicago Midway Airport (average of $58). Flying from Greenville to Chicago Midway Airport in December is currently the most expensive (average of $190). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Greenville to Midway

Discover the top airline that operate flights from Greenville to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$180Average$300FlexibilityNo cancel feeOn-timeN/A

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