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$138+ Cheap flights from Midway (MDW) to Greenville (GSP)

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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GSP
Jun 22 — Jun 291
Mon 6/22
Mon 6/29
1 adult, Economy
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Find cheap flights from Midway to Greenville with Cheapflights

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Cheap flight deals from Midway to Greenville

Cheapest flights from Midway to Greenville
Explore the most affordable flight options available from Midway to Greenville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 23, 2026.

This Southwest deal was found by Cheapflights users on 5/18. 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 5/249:00 am
MDW
-
GSP
1 stop3h 20m
Southwest
Thu 5/286:25 pm
GSP
-
MDW
1 stop6h 05m
Southwest
Deal found 5/18$275
This Delta deal was found by Cheapflights users on 5/18. 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 7/34:25 pm
MDW
-
GSP
1 stop6h 34m
Delta
Thu 7/97:10 am
GSP
-
MDW
1 stop6h 28m
Delta
Deal found 5/18$282
This Southwest deal was found by Cheapflights users on 5/18. 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 6/2411:50 am
MDW
-
GSP
2 stops7h 25m
Southwest
Tue 6/307:50 pm
GSP
-
MDW
1 stop4h 20m
Southwest
Deal found 5/18$287
This Delta deal was found by Cheapflights users on 5/18. 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 8/2112:46 pm
MDW
-
GSP
1 stop5h 18m
Delta
Sun 8/238:49 am
GSP
-
MDW
1 stop4h 02m
Delta
Deal found 5/18$289
This Southwest deal was found by Cheapflights users on 5/20. 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 7/810:00 am
MDW
-
GSP
2 stops8h 00m
Southwest
Sun 7/127:30 pm
GSP
-
MDW
1 stop5h 50m
Southwest
Deal found 5/20$294
This Southwest deal was found by Cheapflights users on 5/19. 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 7/811:25 am
MDW
-
GSP
2 stops6h 35m
Southwest
Tue 7/147:00 am
GSP
-
MDW
2 stops7h 35m
Southwest
Deal found 5/19$299
This Southwest deal was found by Cheapflights users on 5/18. 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 6/125:05 pm
MDW
-
GSP
1 stop4h 45m
Southwest
Mon 6/156:50 pm
GSP
-
MDW
1 stop4h 05m
Southwest
Deal found 5/18$304
This Southwest deal was found by Cheapflights users on 5/19. 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 7/101:00 pm
MDW
-
GSP
2 stops7h 35m
Southwest
Wed 7/157:50 pm
GSP
-
MDW
1 stop4h 20m
Southwest
Deal found 5/19$309
This Southwest deal was found by Cheapflights users on 5/18. 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 6/212:50 pm
MDW
-
GSP
2 stops6h 10m
Southwest
Mon 6/812:55 pm
GSP
-
MDW
1 stop5h 55m
Southwest
Deal found 5/18$314
This Southwest deal was found by Cheapflights users on 5/20. 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 6/206:35 am
MDW
-
GSP
1 stop4h 40m
Southwest
Sat 6/278:40 pm
GSP
-
MDW
1 stop3h 35m
Southwest
Deal found 5/20$319

Find flight deals from Midway to Greenville

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Greenville (GSP). 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 May 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$282
(Delta)

One-way from

$138
(Southwest)

Popular in

March

Cheapest in

January

Average price

$359
Provider with most accurate pricing for Chicago Midway-Greenville flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Greenville flights.
Search Deals
From Chicago Midway to Greenville
Search Deals
One-way flight from Chicago Midway to Greenville
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Greenville 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 May 23, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Greenville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Fri 8/21

6:05 am-12:41 pm

1 stop5h 36m

Greenville

Sun 8/23

7:10 am-12:39 pm

1 stop6h 29m

$289

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Fri 7/31

6:00 am-10:47 am

1 stop3h 47m

Greenville

Sat 8/8

5:20 pm-10:36 pm

1 stop6h 16m

$289

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Wed 6/17

1:26 pm-6:15 pm

1 stop3h 49m

Greenville

Wed 6/24

7:10 am-12:46 pm

1 stop6h 36m

$289

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Wed 7/8

10:00 am-7:00 pm

2 stops8h 00m

Greenville

Sun 7/12

7:30 pm-12:20 am

1 stop5h 50m

$294

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Tue 6/16

5:20 pm-10:00 pm

1 stop3h 40m

Greenville

Sun 6/21

7:30 pm-12:20 am

1 stop5h 50m

$319

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Tue 5/26

12:50 pm-8:00 pm

2 stops6h 10m

Greenville

Fri 5/29

6:25 pm-9:00 pm

1 stop3h 35m

$329
Quickest round-trip

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Mon 6/1

6:15 pm-10:35 pm

1 stop3h 20m

Greenville

Thu 6/4

6:50 pm-9:55 pm

1 stop4h 05m

$329

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Wed 6/17

11:50 am-8:15 pm

2 stops7h 25m

Greenville

Wed 6/24

1:50 pm-5:55 pm

1 stop5h 05m

$333

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Tue 8/18

9:05 am-4:45 pm

1 stop6h 40m

Greenville

Fri 8/21

6:55 pm-10:20 pm

1 stop4h 25m

$334

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Thu 5/28

6:23 am-2:15 pm

1 stop6h 52m

Greenville

Sun 5/31

8:45 am-11:56 am

1 stop4h 11m

$337

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/20

Showing 1-10 of 22 resultsSorted by cheapest first
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Compare providers for flights from Midway to Greenville

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 Midway to Greenville in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 Chicago Midway Airport-Greenville flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Greenville flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Greenville flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Greenville 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 Chicago Midway Airport-Greenville 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 Midway to Greenville

Have a flexible travel schedule? Discover the best time to fly to Greenville from Midway 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 Midway to Greenville. 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 into for flights to Greenville from Chicago Midway?

    If you book a flight to Greenville from Chicago Midway, you will be flying to Greenville, which is the city’s only airport. Greenville (GSP) is located 10.4 mi from the center of Greenville. There are 0 flights from Chicago Midway to Greenville per day from 0 different airlines.

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

    Airlines like Delta and Southwest fly from Chicago Midway Airport to Greenville in about 5h 36m. The time it takes to get you to your destination can typically vary by up to 2h 24m. Airlines will cover a distance of 562 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Greenville 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 Greenville?

Book flights to Greenville if you plan to visit one of these locations
Greer
Simpsonville
Greenwood
Duncan
Seneca

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