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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 12/27. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$213
(Southwest)

One-way from

$108
(Southwest)

Popular in

November

Cheapest in

June

Average price

$232
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. 24% potential increase in price ($110 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Southwest deal was found by Cheapflights users on 9/17. 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.
Wed 10/156:05 amGSP - MDW
2 stops7h 00mSouthwest
Wed 10/229:05 amMDW - GSP
2 stops9h 50mSouthwest
Deal found 9/17$207
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:27 amGSP - MDW
1 stop6h 07mDelta
Tue 12/96:00 amMDW - GSP
1 stop4h 16mDelta
Deal found 9/15$213
This Delta deal was found by Cheapflights users on 9/17. 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 10/166:35 amGSP - MDW
1 stop4h 05mDelta
Mon 10/205:04 pmMDW - GSP
1 stop5h 51mDelta
Deal found 9/17$215
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 12/54:45 pmGSP - MDW
1 stop5h 20mSouthwest
Tue 12/96:40 amMDW - GSP
2 stops8h 25mSouthwest
Deal found 9/14$218
This Delta deal was found by Cheapflights users on 9/17. 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 11/267:27 amGSP - MDW
1 stop6h 07mDelta
Mon 12/15:34 pmMDW - GSP
1 stop5h 21mDelta
Deal found 9/17$222
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:27 amGSP - MDW
1 stop6h 07mDelta
Sun 12/75:32 pmMDW - GSP
1 stop5h 24mDelta
Deal found 9/15$229
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 12/124:15 pmGSP - MDW
1 stop8h 55mSouthwest
Sun 12/145:10 amMDW - GSP
1 stop9h 30mSouthwest
Deal found 9/14$234
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 12/244:45 pmGSP - MDW
1 stop5h 20mSouthwest
Sun 12/289:40 pmMDW - GSP
1 stop11h 25mSouthwest
Deal found 9/15$238
This Delta deal was found by Cheapflights users on 9/16. 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 12/57:27 amGSP - MDW
1 stop6h 07mDelta
Mon 12/85:32 pmMDW - GSP
1 stop5h 24mDelta
Deal found 9/16$243
This Delta deal was found by Cheapflights users on 9/17. 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 10/25:30 amGSP - MDW
1 stop5h 10mDelta
Sun 10/56:00 amMDW - GSP
1 stop4h 04mDelta
Deal found 9/17$249

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 September 17, 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

Wed 10/15

6:05 am-12:05 pm

2 stops7h 00m

Chicago Midway

Wed 10/22

9:05 am-7:55 pm

2 stops9h 50m

$207

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/5

7:27 am-12:34 pm

1 stop6h 07m

Chicago Midway

Tue 12/9

6:00 am-11:16 am

1 stop4h 16m

$213

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/12

4:15 pm-12:10 am

1 stop8h 55m

Chicago Midway

Tue 12/16

12:55 pm-7:50 pm

1 stop5h 55m

$213

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/5

4:45 pm-9:05 pm

1 stop5h 20m

Chicago Midway

Tue 12/9

8:50 am-4:05 pm

1 stop6h 15m

$213

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 10/16

6:35 am-9:40 am

1 stop4h 05m

Chicago Midway

Mon 10/20

5:04 pm-11:55 pm

1 stop5h 51m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/5

10:35 am-4:50 pm

2 stops7h 15m

Chicago Midway

Wed 12/10

7:00 am-2:30 pm

1 stop6h 30m

$218

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/5

7:27 am-12:34 pm

1 stop6h 07m

Chicago Midway

Sun 12/7

5:32 pm-11:56 pm

1 stop5h 24m

$229

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 12/24

4:45 pm-9:05 pm

1 stop5h 20m

Chicago Midway

Sun 12/28

9:40 pm-10:05 am

1 stop11h 25m

$238

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 12/27

8:00 pm-11:20 pm

1 stop4h 20m

$108

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 3/12

6:25 pm-12:05 am

1 stop6h 40m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 15 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 September 17, 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
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 $213, Southwest can have you in Chicago Midway Airport from Greenville in 6h 07m. 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 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 $232 round trip. These flights start at 46% 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$180Average$300FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$232Average$402FlexibilityNo cancel feeOn-time63%

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