$129+ 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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — MDW
May 10 — May 171
Round-trip
1 adult, Economy
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Find cheap flights from Greenville to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Greenville to Midway
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Best
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Cheapest flights from Greenville to MidwayExplore 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 April 10, 2026.
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 April 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:18 pm
GSP
- MDW
2 stops26h 56m
Multiple Airlines
Mon 4/279:14 am
MDW
- GSP
1 stop9h 24m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$240
This Southwest deal was found by Cheapflights users on 4/10. 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 5/135:05 pm
GSP
- MDW
1 stop6h 10m
Southwest
Sun 5/249:00 am
MDW
- GSP
1 stop3h 20m
Southwest
Deal found 4/10![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 4/7. 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 5/86:25 am
GSP
- MDW
1 stop6h 45m
Southwest
Sat 5/162:15 pm
MDW
- GSP
1 stop5h 25m
Southwest
Deal found 4/7![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 4/8. 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 5/16:25 am
GSP
- MDW
1 stop6h 45m
Southwest
Fri 5/85:55 pm
MDW
- GSP
1 stop3h 20m
Southwest
Deal found 4/8![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 4/8. 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 5/235:05 pm
GSP
- MDW
1 stop5h 04m
Delta
Sat 5/305:10 pm
MDW
- GSP
1 stop5h 33m
Delta
Deal found 4/8![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 4/7. 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 5/296:25 pm
GSP
- MDW
1 stop6h 05m
Southwest
Sun 5/317:00 pm
MDW
- GSP
1 stop3h 25m
Southwest
Deal found 4/7![Southwest logo]()
$297
Best flights from Greenville to MidwayDiscover carefully curated flight deals from Greenville to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 10, 2026.
Discover carefully curated flight deals from Greenville to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 10, 2026.
This Southwest deal was found by Cheapflights users on 4/10. 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 5/1312:50 pm
GSP
- MDW
2 stops7h 55m
Southwest
Sun 5/249:00 am
MDW
- GSP
1 stop3h 20m
Southwest
Deal found 4/10![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 4/8. 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 5/27:30 am
GSP
- MDW
1 stop6h 13m
Delta
Sat 5/910:45 am
MDW
- GSP
1 stop4h 32m
Delta
Deal found 4/8![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 4/9. 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.
Mon 5/186:25 pm
GSP
- MDW
1 stop6h 05m
Southwest
Tue 5/197:00 am
MDW
- GSP
1 stop5h 10m
Southwest
Deal found 4/9![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 4/7. 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 5/86:25 am
GSP
- MDW
1 stop6h 45m
Southwest
Sat 5/162:15 pm
MDW
- GSP
1 stop5h 25m
Southwest
Deal found 4/7![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 4/7. 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 6/21:55 pm
GSP
- MDW
2 stops6h 30m
Southwest
Fri 6/55:05 pm
MDW
- GSP
1 stop4h 40m
Southwest
Deal found 4/7![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 4/9. 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 5/96:25 am
GSP
- MDW
2 stops7h 45m
Southwest
Sun 5/1010:50 am
MDW
- GSP
2 stops6h 40m
Southwest
Deal found 4/9![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 4/5. 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 5/112:35 pm
GSP
- MDW
1 stop5h 25m
Southwest
Mon 5/47:30 am
MDW
- GSP
2 stops9h 20m
Southwest
Deal found 4/5![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 4/5. 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 5/11:50 pm
GSP
- MDW
2 stops7h 15m
Southwest
Sun 5/34:15 pm
MDW
- GSP
2 stops6h 10m
Southwest
Deal found 4/5![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 4/8. 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 5/235:25 pm
GSP
- MDW
1 stop6h 10m
Southwest
Sat 5/3012:05 pm
MDW
- GSP
2 stops7h 35m
Southwest
Deal found 4/8![Southwest logo]()
$302
Last-minute flights from Greenville to MidwayDiscover last-minute flight deals from Greenville to Midway. Data last updated April 10, 2026 and is based on user searches.
Discover last-minute flight deals from Greenville to Midway. Data last updated April 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:18 pm
GSP
- MDW
2 stops26h 56m
Multiple Airlines
Mon 4/279:14 am
MDW
- GSP
1 stop9h 24m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$240
This Southwest deal was found by Cheapflights users on 4/8. 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 5/16:25 am
GSP
- MDW
1 stop6h 45m
Southwest
Fri 5/85:55 pm
MDW
- GSP
1 stop3h 20m
Southwest
Deal found 4/8![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 4/7. 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 5/86:25 am
GSP
- MDW
1 stop6h 45m
Southwest
Sat 5/162:15 pm
MDW
- GSP
1 stop5h 25m
Southwest
Deal found 4/7![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 4/10. 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 5/135:05 pm
GSP
- MDW
1 stop6h 10m
Southwest
Sun 5/249:00 am
MDW
- GSP
1 stop3h 20m
Southwest
Deal found 4/10![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 4/8. 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 5/235:05 pm
GSP
- MDW
1 stop5h 04m
Delta
Sat 5/305:10 pm
MDW
- GSP
1 stop5h 33m
Delta
Deal found 4/8![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 4/7. 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 5/296:25 pm
GSP
- MDW
1 stop6h 05m
Southwest
Sun 5/317:00 pm
MDW
- GSP
1 stop3h 25m
Southwest
Deal found 4/7![Southwest logo]()
$297
One-way flights from Greenville to MidwaySearch for one-way flight options from Greenville to Midway. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
Search for one-way flight options from Greenville to Midway. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:23 am
GSP
- MDW
2 stops37h 03m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1610:38 am
GSP
- MDW
1 stop22h 21m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$134
This Southwest deal was found by Cheapflights users on 4/8. 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 5/135:05 pm
GSP
- MDW
1 stop3h 55m
Southwest
Deal found 4/8![Southwest logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/229:51 pm
GSP
- MDW
2 stops14h 21m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2610:23 am
GSP
- MDW
2 stops36h 56m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$142
This Southwest deal was found by Cheapflights users on 4/6. 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 7/36:50 pm
GSP
- MDW
1 stop6h 25m
Southwest
Deal found 4/6![Southwest logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:20 am
GSP
- MDW
2 stops38h 51m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$152
This Southwest deal was found by Cheapflights users on 4/7. 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.
Mon 6/226:50 pm
GSP
- MDW
1 stop6h 25m
Southwest
Deal found 4/7![Southwest logo]()
$160
This Southwest deal was found by Cheapflights users on 4/8. 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 4/238:10 am
GSP
- MDW
1 stop4h 55m
Southwest
Deal found 4/8![Southwest logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/198:25 am
GSP
- MDW
2 stops38h 46m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$169
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 April 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $240 (Kiwi.com) |
One-way from | $129 (Kiwi.com) |
Popular in | March |
Cheapest in | February |
Average price | $269 |
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 April 10, 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
Cheapest round-trip
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Wed 5/13
12:50 pm-7:45 pm
2 stops7h 55m
Chicago Midway
Sun 5/24
9:00 am-1:20 pm
1 stop3h 20m
$280
Quickest round-trip
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Sat 5/2
7:30 am-12:43 pm
1 stop6h 13m
Chicago Midway
Sat 5/9
10:45 am-4:17 pm
1 stop4h 32m
$282
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Mon 5/18
6:25 pm-11:30 pm
1 stop6h 05m
Chicago Midway
Tue 5/19
7:00 am-1:10 pm
1 stop5h 10m
$282
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Fri 5/8
6:25 am-12:10 pm
1 stop6h 45m
Chicago Midway
Sat 5/16
2:15 pm-8:40 pm
1 stop5h 25m
$282
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Tue 6/2
1:55 pm-7:25 pm
2 stops6h 30m
Chicago Midway
Fri 6/5
5:05 pm-10:45 pm
1 stop4h 40m
$287
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Sat 5/9
6:25 am-1:10 pm
2 stops7h 45m
Chicago Midway
Sun 5/10
10:50 am-6:30 pm
2 stops6h 40m
$292
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Fri 5/1
12:35 pm-5:00 pm
1 stop5h 25m
Chicago Midway
Mon 5/4
7:30 am-5:50 pm
2 stops9h 20m
$294
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Fri 5/1
1:50 pm-8:05 pm
2 stops7h 15m
Chicago Midway
Sun 5/3
4:15 pm-11:25 pm
2 stops6h 10m
$299
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Sat 5/23
5:25 pm-10:35 pm
1 stop6h 10m
Chicago Midway
Sat 5/30
12:05 pm-8:40 pm
2 stops7h 35m
$302
Cheapest one-way
Quickest one-way
GreenvilleChicago
GSP - MDW
GSPMDW
Greenville
Wed 6/3
5:05 pm-8:00 pm
1 stop3h 55m
$138
Showing 1-10 of 19 resultsSorted by cheapest first
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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
GSP-MDW
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
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 April 10, 2026.
Read through reviews of airlines operating flights from Greenville to Chicago Midway Airport, such as Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Comfort
7.9
Overall
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Overall
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Alternative routes for Greenville to Midway
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 10, 2026.
Greenville and Midway flights
Browse other Greenville and Midway flight options. Last updated on April 10, 2026.
Other flights from Greenville
Browse through other flights departing from Greenville. Flights are based on user searches made on Cheapflights and were last updated on April 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Greenville to Midway
Discover the top airline 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 April 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$180 | Average$317 | FlexibilityNo cancel fee | On-timeN/A |