$138+ Cheap flights from Greenville (GSP) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — MDW
Nov 15 — Nov 221
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 October 16, 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 October 16, 2026.
This Delta deal was found by Cheapflights users on 10/13. 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 11/75:00 pm -
1 stop6h 33m
Tue 11/1011:27 am -
1 stop5h 52m
Deal found 10/13![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 10/13. 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 11/710:50 am -
2 stops7h 35m
Tue 11/108:00 am -
1 stop5h 10m
Deal found 10/13![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 10/14. 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.
Thu 12/36:45 pm -
1 stop5h 00m
Sun 12/610:15 am -
2 stops8h 55m
Deal found 10/14![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 10/15. 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.
Sat 11/1412:50 pm -
1 stop4h 40m
Sat 11/215:25 am -
1 stop6h 50m
Deal found 10/15![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 10/13. 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.
Tue 11/32:50 pm -
1 stop5h 05m
Thu 11/512:45 pm -
2 stops6h 25m
Deal found 10/13![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 10/14. 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 10/302:10 pm -
1 stop6h 45m
Wed 11/412:50 pm -
1 stop6h 05m
Deal found 10/14![Southwest logo]()
$369
This Delta deal was found by Cheapflights users on 10/13. 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.
Fri 11/612:54 pm -
1 stop6h 06m
Mon 11/96:00 am -
1 stop6h 15m
Deal found 10/13![Delta logo]()
$379
This Southwest deal was found by Cheapflights users on 10/13. 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.
Mon 11/238:50 pm -
1 stop4h 20m
Wed 11/253:05 pm -
1 stop7h 20m
Deal found 10/13![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 10/13. 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 11/158:50 pm -
1 stop4h 20m
Fri 11/2012:45 pm -
2 stops8h 00m
Deal found 10/13![Southwest logo]()
$384
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 October 16, 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 October 16, 2026.
This Southwest deal was found by Cheapflights users on 10/13. 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.
Thu 11/128:50 pm -
1 stop4h 20m
Thu 11/198:00 am -
1 stop5h 10m
Deal found 10/13![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 10/11. 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.
Fri 11/612:54 pm -
1 stop6h 06m
Sun 11/86:04 am -
1 stop5h 56m
Deal found 10/11![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/11. 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 12/28:06 am -
1 stop4h 58m
Sat 12/54:08 pm -
1 stop5h 14m
Deal found 10/11![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 10/11. 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 12/58:25 am -
2 stops10h 00m
Tue 12/812:50 pm -
1 stop6h 00m
Deal found 10/11![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 10/12. 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 11/75:00 pm -
1 stop6h 33m
Tue 11/1011:27 am -
1 stop5h 52m
Deal found 10/12![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 10/13. 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 11/710:50 am -
2 stops7h 35m
Mon 11/94:00 pm -
1 stop6h 00m
Deal found 10/13![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 10/12. 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 12/512:50 pm -
1 stop4h 40m
Sun 12/610:15 am -
2 stops8h 55m
Deal found 10/12![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 10/13. 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.
Thu 12/37:25 pm -
1 stop4h 29m
Sun 12/66:00 am -
1 stop4h 13m
Deal found 10/13![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 10/11. 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.
Thu 11/2611:00 am -
1 stop5h 15m
Sun 11/296:00 am -
1 stop4h 07m
Deal found 10/11![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 10/15. 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.
Sat 11/1412:50 pm -
1 stop4h 40m
Sat 11/215:25 am -
1 stop6h 50m
Deal found 10/15![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 10/14. 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.
Sun 11/158:50 pm -
1 stop4h 20m
Fri 11/2012:45 pm -
2 stops8h 00m
Deal found 10/14![Southwest logo]()
$384
Last-minute flights from Greenville to MidwayDiscover last-minute flight deals from Greenville to Midway. Data last updated October 16, 2026 and is based on user searches.
Discover last-minute flight deals from Greenville to Midway. Data last updated October 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/14. 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 10/302:10 pm -
1 stop6h 45m
Wed 11/412:50 pm -
1 stop6h 05m
Deal found 10/14![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 10/13. 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.
Tue 11/32:50 pm -
1 stop5h 05m
Thu 11/512:45 pm -
2 stops6h 25m
Deal found 10/13![Southwest logo]()
$364
This Delta deal was found by Cheapflights users on 10/13. 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.
Fri 11/612:54 pm -
1 stop6h 06m
Mon 11/96:00 am -
1 stop6h 15m
Deal found 10/13![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/13. 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 11/75:00 pm -
1 stop6h 33m
Tue 11/1011:27 am -
1 stop5h 52m
Deal found 10/13![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 10/13. 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 11/710:50 am -
2 stops7h 35m
Tue 11/108:00 am -
1 stop5h 10m
Deal found 10/13![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 10/13. 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.
Mon 11/96:40 am -
2 stops10h 20m
Tue 11/106:00 am -
2 stops7h 10m
Deal found 10/13![Southwest logo]()
$388
This Delta deal was found by Cheapflights users on 10/15. 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.
Sat 11/147:20 am -
1 stop6h 31m
Mon 11/165:13 pm -
1 stop5h 40m
Deal found 10/15![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 10/13. 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 11/158:50 pm -
1 stop4h 20m
Fri 11/2012:45 pm -
2 stops8h 00m
Deal found 10/13![Southwest logo]()
$384
This Southwest deal was found by Cheapflights users on 10/13. 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.
Mon 11/238:50 pm -
1 stop4h 20m
Wed 11/253:05 pm -
1 stop7h 20m
Deal found 10/13![Southwest logo]()
$383
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 October 16, 2026.
Search for one-way flight options from Greenville to Midway. Find affordable one-way fares based on user searches. Data last updated October 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:52 pm -
3 stops27h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:52 pm -
3 stops21h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:12 am -
2 stops8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:32 pm -
2 stops28h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$168
This Southwest deal was found by Cheapflights users on 10/13. 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.
Thu 11/128:50 pm -
1 stop4h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Southwest logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:52 pm -
3 stops21h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$175
This Southwest deal was found by Cheapflights users on 10/15. 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.
Fri 11/68:50 pm -
1 stop4h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Southwest logo]()
$180
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 October 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (Delta) |
One-way from | $138 (Kiwi.com) |
Popular in | October |
Cheapest in | March |
Average price | $558 |
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 7,457,451 searches. Data last updated October 16, 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
Fri 11/13
8:52 pm-5:47 pm
3 stops21h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$167
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Fri 11/6
8:32 pm-11:47 pm
2 stops28h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$168
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Thu 11/12
8:50 pm-12:10 am
1 stop4h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Thu 12/3
5:40 am-10:28 am
1 stop5h 48m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Fri 11/13
7:33 pm-10:54 pm
1 stop4h 21m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Fri 10/30
8:52 pm-5:47 pm
3 stops21h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$175
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Fri 11/6
8:50 pm-12:10 am
1 stop4h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$180
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Fri 10/30
8:40 pm-11:55 pm
1 stop4h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$190
Quickest round-trip
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Wed 10/28
7:20 pm-10:15 pm
1 stop3h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$190
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Thu 11/12
8:50 pm-12:10 am
1 stop4h 20m
Chicago Midway
Thu 11/19
8:00 am-2:10 pm
1 stop5h 10m
$339
Showing 1-10 of 20 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 October.
| 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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