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$99+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GSP
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap 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 August 14, 2025.

Round-trip from

$189
(Southwest)

One-way from

$99
(Delta)

Popular in

November

Cheapest in

July

Average price

$304
From Chicago Midway to Greenville
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One-way flight from Chicago Midway to Greenville
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Highest demand for flights based on searches. 11% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 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 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 August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/13. 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 9/176:25 amMDW - GSP
1 stop7h 15mSouthwest
Wed 9/246:45 pmGSP - MDW
1 stop5h 35mSouthwest
Deal found 8/13$189
This Delta deal was found by Cheapflights users on 8/12. 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 9/206:00 amMDW - GSP
1 stop6h 09mDelta
Tue 9/237:35 amGSP - MDW
1 stop5h 13mDelta
Deal found 8/12$206
This Southwest deal was found by Cheapflights users on 8/12. 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 11/18:20 amMDW - GSP
2 stops8h 55mSouthwest
Tue 11/44:45 pmGSP - MDW
1 stop5h 20mSouthwest
Deal found 8/12$213
This Southwest deal was found by Cheapflights users on 8/13. 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 11/85:50 amMDW - GSP
1 stop6h 10mSouthwest
Thu 11/134:15 pmGSP - MDW
1 stop6h 35mSouthwest
Deal found 8/13$215
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sun 9/75:35 amMDW - GSP
1 stop4h 05mSouthwest
Tue 9/96:45 pmGSP - MDW
1 stop5h 35mSouthwest
Deal found 8/13$219
This Delta deal was found by Cheapflights users on 8/12. 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 9/51:08 pmMDW - GSP
1 stop5h 15mDelta
Sat 9/66:30 pmGSP - MDW
1 stop3h 42mDelta
Deal found 8/12$222
This Delta deal was found by Cheapflights users on 8/12. 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 9/266:46 pmMDW - GSP
1 stop4h 06mDelta
Sun 9/287:05 amGSP - MDW
1 stop6h 23mDelta
Deal found 8/12$229
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:00 amMDW - GSP
1 stop6h 20mDelta
Sun 9/75:30 amGSP - MDW
1 stop5h 06mDelta
Deal found 8/14$232

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 August 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Greenville that are best for you.

Fly from

Midway

Fly to

Greenville

Route

Depart

Return

Price

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Wed 9/17

6:25 am-2:40 pm

1 stop7h 15m

Greenville

Wed 9/24

6:45 pm-11:20 pm

1 stop5h 35m

$189

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Wed 10/1

6:25 am-2:40 pm

1 stop7h 15m

Greenville

Wed 10/15

3:00 pm-6:30 pm

1 stop4h 30m

$189

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Sat 9/20

6:00 am-1:09 pm

1 stop6h 09m

Greenville

Tue 9/23

7:35 am-11:48 am

1 stop5h 13m

$206

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Sat 11/1

1:11 pm-5:41 pm

1 stop3h 30m

Greenville

Tue 11/4

7:30 am-12:28 pm

1 stop5h 58m

$206

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Thu 10/2

1:08 pm-6:14 pm

1 stop4h 06m

Greenville

Tue 10/7

7:30 am-12:28 pm

1 stop5h 58m

$206

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Sat 11/1

8:20 am-6:15 pm

2 stops8h 55m

Greenville

Tue 11/4

4:45 pm-9:05 pm

1 stop5h 20m

$213

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Sat 11/8

5:50 am-1:00 pm

1 stop6h 10m

Greenville

Thu 11/13

4:15 pm-9:50 pm

1 stop6h 35m

$215

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Wed 9/3

4:25 pm-11:34 pm

1 stop6h 09m

$99

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Thu 10/2

1:08 pm-6:14 pm

1 stop4h 06m

$108

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Mon 9/29

1:08 pm-6:14 pm

1 stop4h 06m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 17 results
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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.

Cheapflights Insights

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Greenville (average of $329). Flying from Chicago Midway Airport to Greenville in March is currently the most expensive (average of $386). 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.

What is the cheapest time of day to fly from MDW to GSP?

Find hourly flight availability from Midway to Greenville. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Greenville at noon. If you’re flexible enough to do this you can expect to save up to 13% on your trip compared to booking a flight in the afternoon.

Reviews of airlines servicing Greenville

Get insights into the airlines that provide service to Greenville. 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 Greenville. Reviews last updated August 14, 2025.
Peruse reviews from past customers who have flown with Southwest and Delta from Chicago Midway Airport to Greenville to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

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
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

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 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 2 different airlines.

  • What are the cheapest airlines flying from Chicago Midway Airport to Greenville round-trip?

    According to our current data, Delta ($214), and Southwest ($278) offers the cheapest pricing from Chicago Midway Airport to Greenville.

  • 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.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Greenville (average of $329). Flying from Chicago Midway Airport to Greenville in March is currently the most expensive (average of $386). 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 Greenville?

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

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Top 2 airlines flying from Midway to Greenville

Discover the top 2 airlines that operate flights from Midway to Greenville. 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$214Average$323FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$278Average$385FlexibilityNo cancel feeOn-time63%

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