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$108+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — MDW
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$215
(Delta)

One-way from

$108
(Southwest)

Popular in

November

Cheapest in

June

Average price

$293
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. 21% potential increase in price ($93 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 18, 2025.

This Delta deal was found by Cheapflights users on 8/17. 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.
Sat 9/275:30 amGSP - MDW
1 stop5h 18mDelta
Tue 9/3012:43 pmMDW - GSP
1 stop3h 35mDelta
Deal found 8/17$215
This Delta deal was found by Cheapflights users on 8/18. 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.
Sat 9/277:05 amGSP - MDW
1 stop6h 23mDelta
Mon 9/291:08 pmMDW - GSP
1 stop4h 06mDelta
Deal found 8/18$216
This Southwest deal was found by Cheapflights users on 8/17. 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 10/188:00 amGSP - MDW
2 stops5h 20mSouthwest
Tue 10/215:15 amMDW - GSP
1 stop8h 10mSouthwest
Deal found 8/17$220
This Delta deal was found by Cheapflights users on 8/18. 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.
Thu 10/27:05 amGSP - MDW
1 stop6h 23mDelta
Sun 10/56:00 amMDW - GSP
1 stop4h 04mDelta
Deal found 8/18$223
This Delta deal was found by Cheapflights users on 8/17. 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.
Thu 11/206:45 amGSP - MDW
1 stop6h 10mDelta
Sun 11/236:00 amMDW - GSP
1 stop3h 56mDelta
Deal found 8/17$229
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sat 11/13:35 pmGSP - MDW
1 stop7h 55mSouthwest
Tue 11/47:00 amMDW - GSP
1 stop6h 30mSouthwest
Deal found 8/18$232
This Delta deal was found by Cheapflights users on 8/17. 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.
Sat 8/305:15 pmGSP - MDW
1 stop4h 57mDelta
Sun 8/314:25 pmMDW - GSP
1 stop6h 34mDelta
Deal found 8/17$237
This Delta deal was found by Cheapflights users on 8/17. 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 9/37:05 amGSP - MDW
1 stop6h 23mDelta
Sat 9/66:00 amMDW - GSP
1 stop4h 29mDelta
Deal found 8/17$239
This Delta deal was found by Cheapflights users on 8/17. 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.
Sat 8/305:15 pmGSP - MDW
1 stop4h 57mDelta
Fri 9/51:08 pmMDW - GSP
1 stop5h 15mDelta
Deal found 8/17$243
This Delta deal was found by Cheapflights users on 8/17. 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 8/277:05 amGSP - MDW
1 stop6h 23mDelta
Sat 8/301:08 pmMDW - GSP
1 stop5h 15mDelta
Deal found 8/17$250

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 August 18, 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

Sat 9/20

5:21 pm-9:10 pm

1 stop4h 49m

Chicago Midway

Wed 9/24

6:00 am-11:24 am

1 stop4h 24m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 11/1

7:30 am-12:31 pm

1 stop6h 01m

Chicago Midway

Tue 11/4

5:09 pm-11:54 pm

1 stop5h 45m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 10/4

7:05 am-12:28 pm

1 stop6h 23m

Chicago Midway

Tue 10/7

1:08 pm-5:50 pm

1 stop3h 42m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 10/18

7:30 am-12:31 pm

1 stop6h 01m

Chicago Midway

Tue 10/21

6:00 am-12:47 pm

1 stop5h 47m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 9/23

6:13 pm-9:36 pm

1 stop4h 23m

Chicago Midway

Sat 9/27

11:00 am-4:16 pm

1 stop4h 16m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 9/20

5:21 pm-9:10 pm

1 stop4h 49m

Chicago Midway

Tue 9/23

12:43 pm-5:18 pm

1 stop3h 35m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 9/24

7:05 am-12:28 pm

1 stop6h 23m

Chicago Midway

Sat 9/27

11:00 am-4:16 pm

1 stop4h 16m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 9/27

5:21 pm-9:10 pm

1 stop4h 49m

Chicago Midway

Tue 9/30

6:00 am-11:24 am

1 stop4h 24m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 10/7

6:05 am-12:00 pm

1 stop6h 55m

$108

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 9/17

6:45 pm-11:20 pm

1 stop5h 35m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 16 results
1
2

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, April is the cheapest month in which you can book a flight from Greenville to Chicago Midway Airport (average of $160). Flying from Greenville to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 August 18, 2025.
Read through reviews of airlines operating flights from Greenville to Chicago Midway Airport, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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. 2 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 $215, Delta can have you in Chicago Midway Airport from Greenville in 4h 49m. The distance between Greenville and Chicago Midway Airport is about 562 mi.

  • What are the cheapest airlines flying 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. Another option worth looking into is Southwest, starting at $304 round trip. These flights start at 48% 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, April is the cheapest month in which you can book a flight from Greenville to Chicago Midway Airport (average of $160). Flying from Greenville to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 2 airlines flying from Greenville to Midway

Discover the top 2 airlines 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$180Average$300FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$304Average$402FlexibilityNo cancel feeOn-time63%

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