HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$75+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — MDW
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
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

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 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$211
(Southwest)

One-way from

$75
(Southwest)

Popular in

November

Cheapest in

June

Average price

$286
Provider with most accurate pricing for Greenville-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Greenville-Chicago Midway flights.
Search Deals
From Greenville to Chicago Midway
Search Deals
One-way flight from Greenville to Chicago Midway
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find flight deals from Greenville to Midway

Cheapest flights from Greenville to Midway
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 23, 2025.

This Southwest deal was found by Cheapflights users on 10/21. 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 12/54:45 pmGSP - MDW
1 stop5h 20mSouthwest
Tue 12/96:40 amMDW - GSP
2 stops8h 25mSouthwest
Deal found 10/21$211
This Delta deal was found by Cheapflights users on 10/21. 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 12/137:25 amGSP - MDW
1 stop6h 09mDelta
Tue 1/66:00 amMDW - GSP
1 stop6h 54mDelta
Deal found 10/21$215
This Delta deal was found by Cheapflights users on 10/21. 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.
Sun 12/147:25 amGSP - MDW
1 stop6h 09mDelta
Tue 1/66:00 amMDW - GSP
1 stop6h 54mDelta
Deal found 10/21$222
This Southwest deal was found by Cheapflights users on 10/21. 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 12/68:10 amGSP - MDW
2 stops11h 35mSouthwest
Tue 12/95:00 amMDW - GSP
2 stops10h 05mSouthwest
Deal found 10/21$224
This Delta deal was found by Cheapflights users on 10/23. 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 12/56:45 amGSP - MDW
1 stop3h 56mDelta
Mon 12/85:29 pmMDW - GSP
1 stop5h 11mDelta
Deal found 10/23$229
This Southwest deal was found by Cheapflights users on 10/20. 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 10/313:05 pmGSP - MDW
1 stop6h 15mSouthwest
Tue 11/48:50 amMDW - GSP
1 stop6h 15mSouthwest
Deal found 10/20$232
This Southwest deal was found by Cheapflights users on 10/20. 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 10/313:05 pmGSP - MDW
1 stop6h 15mSouthwest
Mon 11/311:25 amMDW - GSP
2 stops7h 25mSouthwest
Deal found 10/20$237
This Delta deal was found by Cheapflights users on 10/21. 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 11/75:30 amGSP - MDW
1 stop5h 15mDelta
Mon 11/105:34 pmMDW - GSP
1 stop5h 11mDelta
Deal found 10/21$239
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/143:55 pmGSP - MDW
2 stops27h 44mMultiple Airlines
Mon 11/179:27 amMDW - GSP
1 stop8h 56mMultiple Airlines
Deal found 10/22$248
This Delta deal was found by Cheapflights users on 10/22. 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 11/55:30 amGSP - MDW
1 stop5h 15mDelta
Sat 11/84:23 pmMDW - GSP
1 stop6h 32mDelta
Deal found 10/22$249
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 10/318:03 pmGSP - MDW
1 stop15h 23mMultiple Airlines
Mon 11/39:32 amMDW - GSP
1 stop8h 51mMultiple Airlines
Deal found 10/20$250
This Delta deal was found by Cheapflights users on 10/23. 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 12/57:25 amGSP - MDW
1 stop6h 09mDelta
Sun 12/76:00 amMDW - GSP
1 stop4h 15mDelta
Deal found 10/23$254

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 October 23, 2025.
Use the filters below to find and compare flights from Greenville to Chicago Midway Airport that are best for you.

Fly from

Greenville

Fly to

Midway

Route

Depart

Return

Price

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 12/13

7:25 am-12:34 pm

1 stop6h 09m

Chicago Midway

Tue 1/6

6:00 am-1:54 pm

1 stop6h 54m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 12/16

5:35 am-9:41 am

1 stop5h 06m

Chicago Midway

Tue 1/6

6:00 am-11:00 am

1 stop4h 00m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sun 12/14

7:25 am-12:34 pm

1 stop6h 09m

Chicago Midway

Tue 1/6

6:00 am-1:54 pm

1 stop6h 54m

$222

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Mon 12/15

7:36 pm-11:47 pm

1 stop5h 11m

Chicago Midway

Tue 1/6

6:00 am-1:54 pm

1 stop6h 54m

$222

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/5

6:45 am-9:41 am

1 stop3h 56m

Chicago Midway

Mon 12/8

5:29 pm-11:40 pm

1 stop5h 11m

$229

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/12

5:35 am-9:41 am

1 stop5h 06m

Chicago Midway

Sun 12/14

5:13 pm-11:40 pm

1 stop5h 27m

$229

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 11/12

5:35 am-9:52 am

1 stop5h 17m

Chicago Midway

Sat 11/15

6:00 am-1:10 pm

1 stop6h 10m

$229

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 11/13

5:35 am-9:52 am

1 stop5h 17m

Chicago Midway

Sat 11/15

4:28 pm-9:17 pm

1 stop3h 49m

$229

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 11/14

5:35 am-9:52 am

1 stop5h 17m

Chicago Midway

Mon 11/17

5:34 pm-10:34 pm

1 stop4h 00m

$229

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 11/7

5:30 am-9:45 am

1 stop5h 15m

Chicago Midway

Mon 11/10

5:34 pm-11:45 pm

1 stop5h 11m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 20 results
1
2

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.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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

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

Currently, August is the cheapest month in which you can book a flight from Greenville to Chicago Midway Airport (average of $58). Flying from Greenville to Chicago Midway Airport in January is currently the most expensive (average of $197). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 October 23, 2025.
Read through reviews of airlines operating flights from Greenville to Chicago Midway Airport, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,982 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • What airport do you fly from for flights from Greenville to Chicago Midway?

    For a flight from Greenville to Chicago Midway, you will be flying from Greenville. Greenville (GSP) is just 10.4 mi from the center of the city. Greenville is the only Greenville airport and it handles 0 outbound flights to Chicago Midway per day. 2 airlines have flights to Chicago Midway from Greenville on a regular basis.

  • How long is the flight from Greenville to Chicago Midway Airport?

    For as low as $215, Delta can have you in Chicago Midway Airport from Greenville in 6h 09m. The distance between Greenville and Chicago Midway Airport is about 562 mi.

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

    Flying on Delta is currently your cheapest option to Chicago Midway Airport, with prices starting at $180. Another option worth looking into is Southwest, starting at $232 round trip. These flights start at 45% lower than the current average price 3 months from now.

  • Can I find deals for flights from Greenville to Midway that include hotel bookings?

    Yes. In addition to deals on Greenville to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Greenville to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Greenville to Midway.

  • Can I find deals for business class flights from Greenville to Midway?

    Yes. Cheapflights offers flight deals from Greenville to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, August is the cheapest month in which you can book a flight from Greenville to Chicago Midway Airport (average of $58). Flying from Greenville to Chicago Midway Airport in January is currently the most expensive (average of $197). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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.

Top 2 airlines flying from Greenville to Midway

Discover the top 2 airlines 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$180Average$300FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$232Average$430FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.