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$145+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — MDW
Aug 15 — Aug 221
Sat 8/15
Sat 8/22
1 adult, Economy
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Cheap 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 July 16, 2026.

This Southwest deal was found by Cheapflights users on 7/13. 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 8/286:55 pm
GSP
-
MDW
1 stop4h 25m
Southwest
Mon 8/318:00 am
MDW
-
GSP
1 stop3h 30m
Southwest
Deal found 7/13$284
This Southwest deal was found by Cheapflights users on 7/13. 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.
Sat 8/1511:05 am
GSP
-
MDW
1 stop4h 05m
Southwest
Wed 8/1912:45 pm
MDW
-
GSP
1 stop5h 40m
Southwest
Deal found 7/13$289
This Southwest deal was found by Cheapflights users on 7/14. 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.
Thu 8/134:40 pm
GSP
-
MDW
2 stops6h 40m
Southwest
Mon 8/173:20 pm
MDW
-
GSP
1 stop5h 15m
Southwest
Deal found 7/14$294
This Southwest deal was found by Cheapflights users on 7/13. 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.
Thu 9/246:55 pm
GSP
-
MDW
1 stop4h 25m
Southwest
Mon 9/287:55 am
MDW
-
GSP
2 stops9h 25m
Southwest
Deal found 7/13$300
This Southwest deal was found by Cheapflights users on 7/15. 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.
Thu 8/64:40 pm
GSP
-
MDW
1 stop5h 20m
Southwest
Sun 8/97:35 am
MDW
-
GSP
1 stop4h 05m
Southwest
Deal found 7/15$304
This Southwest deal was found by Cheapflights users on 7/13. 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 8/1911:00 am
GSP
-
MDW
2 stops6h 50m
Southwest
Mon 8/247:55 am
MDW
-
GSP
2 stops9h 25m
Southwest
Deal found 7/13$305
This Southwest deal was found by Cheapflights users on 7/15. 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.
Tue 8/41:20 pm
GSP
-
MDW
1 stop5h 50m
Southwest
Tue 8/1812:45 pm
MDW
-
GSP
1 stop5h 40m
Southwest
Deal found 7/15$309
This Southwest deal was found by Cheapflights users on 7/14. 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.
Sat 8/156:45 am
GSP
-
MDW
2 stops8h 35m
Southwest
Thu 8/208:45 am
MDW
-
GSP
2 stops6h 20m
Southwest
Deal found 7/14$310

Find 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 July 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$284
(Southwest)

One-way from

$145
(Southwest)

Popular in

June

Cheapest in

February

Average price

$313
Provider with most accurate pricing for Greenville-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Greenville-Chicago Midway flights.
Search Deals
From Greenville to Chicago Midway
Search Deals
One-way flight from Greenville to Chicago Midway
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 16, 2026.
Use the filters below to find and compare flights from Greenville to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 11/17

6:45 am-11:56 am

1 stop6h 11m

Chicago Midway

Mon 11/23

6:00 am-1:08 pm

1 stop6h 08m

$289

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 8/6

8:40 am-2:05 pm

1 stop6h 25m

Chicago Midway

Mon 8/10

3:20 pm-9:35 pm

1 stop5h 15m

$289

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 10/6

5:40 am-9:52 am

1 stop5h 12m

Chicago Midway

Sat 10/10

6:00 am-1:08 pm

1 stop6h 08m

$289

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 10/30

6:45 am-9:52 am

1 stop4h 07m

Chicago Midway

Tue 11/3

6:00 am-1:08 pm

1 stop6h 08m

$289

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 9/25

6:25 pm-10:45 pm

1 stop5h 20m

Chicago Midway

Sun 9/27

6:05 am-12:50 pm

1 stop5h 45m

$289

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 10/29

6:45 am-9:52 am

1 stop4h 07m

Chicago Midway

Sun 11/1

1:00 pm-8:14 pm

1 stop6h 14m

$289

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 11/20

7:15 am-12:33 pm

1 stop6h 18m

Chicago Midway

Sun 11/22

6:00 am-10:58 am

1 stop3h 58m

$289

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 9/2

10:04 am-3:44 pm

1 stop6h 40m

Chicago Midway

Wed 9/9

11:35 am-5:46 pm

1 stop5h 11m

$289
Quickest round-trip

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 8/7

6:55 am-9:59 am

1 stop4h 04m

Chicago Midway

Tue 8/11

12:46 pm-6:45 pm

1 stop4h 59m

$289
Cheapest one-way

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sun 10/4

6:15 am-10:00 am

1 stop4h 45m

$145

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/14

Showing 1-10 of 19 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Greenville-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

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. 0 airlines have 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 $289, Delta can have you in Chicago Midway Airport from Greenville in 6h 11m. The distance between Greenville and Chicago Midway Airport is about 562 mi.

  • 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.

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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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