$100+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — MDW
Sep 13 — Sep 201
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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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One-way
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 August 14, 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 August 14, 2026.
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.
Thu 9/246:55 pm -
1 stop4h 30m
Mon 9/283:20 pm -
1 stop5h 20m
Deal found 8/12![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 8/10. 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.
Thu 8/274:40 pm -
2 stops6h 40m
Mon 8/318:00 am -
1 stop3h 30m
Deal found 8/10![Southwest logo]()
$270
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.
Fri 9/44:40 pm -
1 stop5h 20m
Sun 9/68:55 am -
1 stop3h 45m
Deal found 8/12![Southwest logo]()
$274
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 8/293:30 pm -
1 stop4h 50m
Sat 9/511:45 am -
2 stops6h 15m
Deal found 8/13![Southwest logo]()
$275
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 8/293:30 pm -
1 stop4h 50m
Tue 9/12:40 pm -
1 stop5h 15m
Deal found 8/13![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/10. 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.
Fri 11/208:50 pm -
1 stop4h 15m
Mon 11/2311:10 am -
2 stops8h 00m
Deal found 8/10![Southwest logo]()
$284
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.
Thu 11/128:50 pm -
1 stop4h 15m
Sun 11/156:30 pm -
1 stop3h 25m
Deal found 8/12![Southwest logo]()
$288
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 August 14, 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 August 14, 2026.
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 8/293:30 pm -
1 stop4h 50m
Sat 9/511:45 am -
2 stops6h 15m
Deal found 8/13![Southwest logo]()
$275
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 11/67:10 am -
1 stop6h 37m
Sun 11/86:04 am -
1 stop3h 56m
Deal found 8/12![Delta logo]()
$299
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 8/298:40 am -
2 stops5h 25m
Tue 9/17:40 am -
1 stop3h 45m
Deal found 8/13![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 8/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:15 am -
1 stop6h 24m
Sat 10/311:35 am -
1 stop5h 11m
Deal found 8/9![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 8/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:40 am -
1 stop5h 23m
Sun 11/16:04 am -
1 stop5h 35m
Deal found 8/10![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/9. 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.
Tue 9/228:15 am -
2 stops5h 50m
Tue 9/298:15 am -
2 stops7h 30m
Deal found 8/9![Southwest logo]()
$309
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.
Sun 9/277:20 am -
2 stops7h 30m
Wed 9/307:40 am -
1 stop3h 45m
Deal found 8/12![Southwest logo]()
$330
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.
Fri 8/285:46 am -
1 stop5h 13m
Mon 8/316:05 am -
1 stop5h 36m
Deal found 8/14![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 8/11. 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 9/210:04 am -
1 stop6h 40m
Wed 9/911:35 am -
1 stop5h 11m
Deal found 8/11![Delta logo]()
$339
Last-minute flights from Greenville to MidwayDiscover last-minute flight deals from Greenville to Midway. Data last updated August 14, 2026 and is based on user searches.
Discover last-minute flight deals from Greenville to Midway. Data last updated August 14, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/10. 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.
Thu 8/274:40 pm -
2 stops6h 40m
Mon 8/318:00 am -
1 stop3h 30m
Deal found 8/10![Southwest logo]()
$270
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 8/293:30 pm -
1 stop4h 50m
Sat 9/511:45 am -
2 stops6h 15m
Deal found 8/13![Southwest logo]()
$275
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 8/293:30 pm -
1 stop4h 50m
Tue 9/12:40 pm -
1 stop5h 15m
Deal found 8/13![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/11. 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 9/211:00 am -
2 stops8h 45m
Fri 9/41:05 pm -
2 stops7h 30m
Deal found 8/11![Southwest logo]()
$300
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.
Fri 9/44:40 pm -
1 stop5h 20m
Sun 9/68:55 am -
1 stop3h 45m
Deal found 8/12![Southwest logo]()
$274
This Southwest deal was found by Cheapflights users on 8/9. 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.
Tue 9/221:20 pm -
1 stop6h 25m
Tue 9/296:30 am -
2 stops9h 15m
Deal found 8/9![Southwest logo]()
$304
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.
Thu 9/246:55 pm -
1 stop4h 30m
Mon 9/283:20 pm -
1 stop5h 20m
Deal found 8/12![Southwest logo]()
$269
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:49 pm -
1 stop6h 33m
Tue 9/291:00 pm -
1 stop6h 37m
Deal found 8/13![Delta logo]()
$299
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 August 14, 2026.
Search for one-way flight options from Greenville to Midway. Find affordable one-way fares based on user searches. Data last updated August 14, 2026.
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 8/314:40 pm -
1 stop5h 20m
Deal found 8/10![Southwest logo]()
$100
This Southwest deal was found by Cheapflights users on 8/9. 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 1/117:05 pm -
1 stop3h 45m
Deal found 8/9![Southwest logo]()
$112
This Southwest deal was found by Cheapflights users on 8/10. 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.
Fri 9/46:55 pm -
1 stop4h 30m
Deal found 8/10![Southwest logo]()
$125
This Southwest deal was found by Cheapflights users on 8/11. 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 9/56:45 am -
2 stops7h 35m
Deal found 8/11![Southwest logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:41 pm -
2 stops29h 06m
Deal found 8/9![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:37 am -
2 stops36h 54m
Deal found 8/9![Multiple Airlines logo]()
$143
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:40 pm -
1 stop4h 15m
Deal found 8/14![Southwest logo]()
$150
This Southwest deal was found by Cheapflights users on 8/9. 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.
Fri 8/286:55 pm -
1 stop4h 25m
Deal found 8/9![Southwest logo]()
$170
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 August 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $269 (Southwest) |
One-way from | $100 (Southwest) |
Popular in | July |
Cheapest in | February |
Average price | $333 |
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 14, 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 Greenville - MDW Chicago Midway
GSPMDW
Greenville
Sat 8/29
3:30 pm-7:20 pm
1 stop4h 50m
Chicago Midway
Sat 9/5
11:45 am-7:00 pm
2 stops6h 15m
$275
Quickest round-trip
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Sat 8/29
8:40 am-1:05 pm
2 stops5h 25m
Chicago Midway
Tue 9/1
7:40 am-12:25 pm
1 stop3h 45m
$287
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Fri 11/6
7:10 am-12:47 pm
1 stop6h 37m
Chicago Midway
Sun 11/8
6:04 am-11:00 am
1 stop3h 56m
$299
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Wed 9/30
7:15 am-12:39 pm
1 stop6h 24m
Chicago Midway
Sat 10/3
11:35 am-5:46 pm
1 stop5h 11m
$299
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Tue 10/27
5:40 am-10:03 am
1 stop5h 23m
Chicago Midway
Sun 11/1
6:04 am-12:39 pm
1 stop5h 35m
$299
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Tue 9/22
8:15 am-1:05 pm
2 stops5h 50m
Chicago Midway
Tue 9/29
8:15 am-4:45 pm
2 stops7h 30m
$309
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Sun 9/27
7:20 am-1:50 pm
2 stops7h 30m
Chicago Midway
Wed 9/30
7:40 am-12:25 pm
1 stop3h 45m
$330
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Fri 8/28
5:46 am-9:59 am
1 stop5h 13m
Chicago Midway
Mon 8/31
6:05 am-12:41 pm
1 stop5h 36m
$339
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Wed 9/2
10:04 am-3:44 pm
1 stop6h 40m
Chicago Midway
Wed 9/9
11:35 am-5:46 pm
1 stop5h 11m
$339
Cheapest one-way
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Tue 10/6
7:00 am-10:55 am
1 stop4h 55m
$100
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 August.
| 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.
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 locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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