$112+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — MDW
Nov 8 — Nov 151
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
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 9, 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 9, 2026.
This Southwest deal was found by Cheapflights users on 10/8. 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 11/74:55 pm -
1 stop3h 45m
Sat 11/141:25 pm -
1 stop5h 10m
Deal found 10/8![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 10/7. 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.
Wed 11/112:50 pm -
1 stop5h 05m
Thu 11/1211:10 am -
2 stops8h 00m
Deal found 10/7![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 10/6. 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.
Wed 11/112:50 pm -
2 stops6h 00m
Sat 11/1410:20 am -
2 stops8h 15m
Deal found 10/6![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 10/6. 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.
Sat 11/74:55 pm -
1 stop3h 45m
Tue 11/1012:50 pm -
1 stop6h 05m
Deal found 10/6![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 10/6. 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.
Thu 11/58:50 pm -
1 stop4h 20m
Mon 11/98:45 am -
2 stops10h 25m
Deal found 10/6![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 10/8. 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 11/51:00 pm -
2 stops8h 05m
Tue 11/1011:30 am -
2 stops8h 20m
Deal found 10/8![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 10/8. 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 10/228:40 pm -
1 stop4h 15m
Tue 10/272:10 pm -
1 stop3h 20m
Deal found 10/8![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 10/6. 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.
Sun 11/18:50 pm -
1 stop4h 15m
Tue 11/312:45 pm -
1 stop4h 25m
Deal found 10/6![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 10/8. 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 11/131:00 pm -
2 stops8h 25m
Mon 11/1611:30 am -
2 stops8h 20m
Deal found 10/8![Southwest logo]()
$321
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 9, 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 9, 2026.
This Southwest deal was found by Cheapflights users on 10/4. 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 11/131:00 pm -
2 stops8h 25m
Mon 11/1611:30 am -
2 stops8h 20m
Deal found 10/4![Southwest logo]()
$321
This Delta deal was found by Cheapflights users on 10/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:33 pm -
1 stop4h 21m
Sun 11/156:00 am -
1 stop6h 15m
Deal found 10/6![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 10/8. 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 11/138:50 pm -
1 stop4h 20m
Sun 11/158:45 am -
2 stops10h 25m
Deal found 10/8![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 10/6. 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 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 10/6![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 10/4. 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 12/256:45 pm -
1 stop4h 55m
Fri 1/18:00 am -
1 stop5h 10m
Deal found 10/4![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 10/9. 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.
Sun 11/88:50 pm -
1 stop4h 20m
Mon 11/1611:30 am -
2 stops8h 20m
Deal found 10/9![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 10/5. 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.
Thu 11/268:15 am -
1 stop4h 40m
Mon 11/303:05 pm -
1 stop7h 20m
Deal found 10/5![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 10/8. 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 12/246:45 pm -
1 stop4h 55m
Tue 12/293:40 pm -
2 stops6h 40m
Deal found 10/8![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 10/7. 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 11/68:50 pm -
1 stop4h 20m
Sun 11/88:45 am -
2 stops10h 25m
Deal found 10/7![Southwest logo]()
$370
This Southwest deal was found by Cheapflights users on 10/6. 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.
Mon 11/96:40 am -
2 stops10h 20m
Tue 11/106:00 am -
2 stops7h 10m
Deal found 10/6![Southwest logo]()
$371
Last-minute flights from Greenville to MidwayDiscover last-minute flight deals from Greenville to Midway. Data last updated October 9, 2026 and is based on user searches.
Discover last-minute flight deals from Greenville to Midway. Data last updated October 9, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/8. 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 10/228:40 pm -
1 stop4h 15m
Tue 10/272:10 pm -
1 stop3h 20m
Deal found 10/8![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 10/6. 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.
Sun 11/18:50 pm -
1 stop4h 15m
Tue 11/312:45 pm -
1 stop4h 25m
Deal found 10/6![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 10/6. 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.
Thu 11/58:50 pm -
1 stop4h 20m
Mon 11/98:45 am -
2 stops10h 25m
Deal found 10/6![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 10/8. 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 11/51:00 pm -
2 stops8h 05m
Tue 11/1011:30 am -
2 stops8h 20m
Deal found 10/8![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 10/8. 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 11/74:55 pm -
1 stop3h 45m
Sat 11/141:25 pm -
1 stop5h 10m
Deal found 10/8![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 10/6. 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.
Sat 11/74:55 pm -
1 stop3h 45m
Tue 11/1012:50 pm -
1 stop6h 05m
Deal found 10/6![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 10/7. 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.
Wed 11/112:50 pm -
1 stop5h 05m
Thu 11/1211:10 am -
2 stops8h 00m
Deal found 10/7![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 10/6. 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.
Wed 11/112:50 pm -
2 stops6h 00m
Sat 11/1410:20 am -
2 stops8h 15m
Deal found 10/6![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 10/8. 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 11/131:00 pm -
2 stops8h 25m
Mon 11/1611:30 am -
2 stops8h 20m
Deal found 10/8![Southwest logo]()
$321
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 9, 2026.
Search for one-way flight options from Greenville to Midway. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
This Southwest deal was found by Cheapflights users on 10/6. 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.
Mon 11/166:45 pm -
1 stop5h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Southwest logo]()
$112
This Southwest deal was found by Cheapflights users on 10/8. 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.
Tue 11/107:05 am -
2 stops8h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 10/6. 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.
Mon 11/168:52 pm -
3 stops27h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 11/510:12 am -
2 stops14h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 10/6. 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.
Thu 10/296:08 pm -
2 stops24h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1711:28 am -
3 stops37h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$164
This Southwest deal was found by Cheapflights users on 10/9. 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.
Thu 11/128:50 pm -
1 stop4h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 10/5. 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.
Tue 10/207:20 pm -
1 stop3h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Southwest logo]()
$190
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 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (Southwest) |
One-way from | $112 (Southwest) |
Popular in | July |
Cheapest in | February |
Average price | $352 |
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 9, 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
Thu 11/5
8:50 pm-12:10 am
1 stop4h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$112
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Tue 11/10
8:05 am-2:40 pm
1 stop7h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$112
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Mon 11/16
6:45 pm-10:45 pm
1 stop5h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$112
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Tue 11/17
2:50 pm-6:55 pm
1 stop5h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$112
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Wed 11/18
11:20 am-4:15 pm
1 stop5h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$112
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Thu 12/10
6:45 pm-10:40 pm
1 stop4h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$112
Quickest round-trip
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Thu 10/29
8:40 pm-11:55 pm
1 stop4h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$112
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Mon 11/16
2:42 pm-11:47 pm
2 stops34h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$125
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Fri 11/13
1:00 pm-8:25 pm
2 stops8h 25m
Chicago Midway
Mon 11/16
11:30 am-8:50 pm
2 stops8h 20m
$321
GreenvilleChicago
GSP Greenville - MDW Chicago Midway
GSPMDW
Greenville
Fri 11/13
8:50 pm-12:10 am
1 stop4h 20m
Chicago Midway
Sun 11/15
8:45 am-8:10 pm
2 stops10h 25m
$335
Showing 1-10 of 18 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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Midway flight routes
Other flight options
Other flights from Greenville
Popular flights