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Cheap flights from Greenville to Chicago from $125

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Greenville to Chicago departing on 11/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Greenville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:25 am - 12:34 pmGSP-MDW
6h 09m1 stop
Delta Logo
11:21 am - 6:55 pmMDW-GSP
6h 34m1 stop
$215Delta
Find Deal
Thu, Dec 18 - Tue, Jan 13
Southwest Logo
7:40 am - 1:45 pmGSP-MDW
7h 05m1 stop
Southwest Logo
11:00 am - 9:35 pmMDW-GSP
9h 35m2 stops
$220Southwest
Find Deal
Mon, Dec 15 - Thu, Dec 18
Delta Logo
7:25 am - 12:34 pmGSP-MDW
6h 09m1 stop
Delta Logo
5:29 pm - 10:33 pmMDW-GSP
4h 04m1 stop
$222Delta
Find Deal
Fri, Dec 5 - Mon, Dec 8
Southwest Logo
7:40 am - 1:00 pmGSP-MDW
6h 20m2 stops
Southwest Logo
11:00 am - 9:35 pmMDW-GSP
9h 35m2 stops
$225Southwest
Find Deal
Mon, Dec 15 - Thu, Dec 18
Delta Logo
6:45 am - 9:54 amGSP-MDW
4h 09m1 stop
Delta Logo
5:13 pm - 10:33 pmMDW-GSP
4h 20m1 stop
$229Delta
Find Deal
Fri, Dec 5 - Sun, Dec 7
Delta Logo
7:36 pm - 11:47 pmGSP-MDW
5h 11m1 stop
Delta Logo
1:28 pm - 6:02 pmMDW-GSP
3h 34m1 stop
$237Delta
Find Deal
Mon, Dec 15 - Thu, Jan 8
Delta Logo
6:45 am - 9:54 amGSP-MDW
4h 09m1 stop
Delta Logo
5:31 pm - 11:55 pmMDW-GSP
5h 24m1 stop
$247Delta
Find Deal
Fri, Dec 19 - Wed, Jan 7
Delta Logo
5:35 am - 9:54 amGSP-MDW
5h 19m1 stop
Delta Logo
6:00 am - 11:15 amMDW-GSP
4h 15m1 stop
$254Delta
Find Deal
Fri, Dec 5 - Sun, Dec 7
Southwest Logo
1:55 pm - 8:35 pmGSP-MDW
7h 40m1 stop
Southwest Logo
7:00 am - 2:30 pmMDW-GSP
6h 30m1 stop
$258Southwest
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Sat, Dec 13 - Wed, Dec 17
Multiple Airlines Logo
4:18 pm - 10:43 pmGSP-MDW
31h 25m2 stops
Multiple Airlines Logo
5:30 pm - 7:23 pmMDW-GSP
24h 53m1 stop
$375Multiple Airlines
Find Deal
Tue, Nov 25 - Sun, Nov 30

Delta flights from Greenville to Chicago Midway Airport

Our best Delta deals on Greenville to Chicago Midway Airport flight tickets
Delta
Dec 18
GSP7:25 amGreenville
6h 09m
1 stop
MDW12:34 pmChicago Midway
Jan 13
MDW11:21 amChicago Midway
6h 34m
1 stop
GSP6:55 pmGreenville
$215
Find similar
Delta
Dec 5
GSP7:25 amGreenville
6h 09m
1 stop
MDW12:34 pmChicago Midway
Dec 8
MDW5:29 pmChicago Midway
4h 04m
1 stop
GSP10:33 pmGreenville
$222
Find similar
Delta
Dec 5
GSP6:45 amGreenville
4h 09m
1 stop
MDW9:54 amChicago Midway
Dec 7
MDW5:13 pmChicago Midway
4h 20m
1 stop
GSP10:33 pmGreenville
$229
Find similar

Southwest flights from Greenville to Chicago Midway Airport

Our best Southwest deals on Greenville to Chicago Midway Airport flight tickets
Southwest
Dec 15
GSP7:40 amGreenville
7h 05m
1 stop
MDW1:45 pmChicago Midway
Dec 18
MDW11:00 amChicago Midway
9h 35m
2 stops
GSP9:35 pmGreenville
$220
Find similar
Southwest
Dec 15
GSP7:40 amGreenville
6h 20m
2 stops
MDW1:00 pmChicago Midway
Dec 18
MDW11:00 amChicago Midway
9h 35m
2 stops
GSP9:35 pmGreenville
$225
Find similar
Southwest
Dec 13
GSP1:55 pmGreenville
7h 40m
1 stop
MDW8:35 pmChicago Midway
Dec 17
MDW7:00 amChicago Midway
6h 30m
1 stop
GSP2:30 pmGreenville
$258
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Greenville to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated October 28, 2025.
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

Price

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 12/18

7:25 am-12:34 pm

1 stop6h 09m

Chicago Midway

Tue 1/13

11:21 am-6:55 pm

1 stop6h 34m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Mon 12/15

7:40 am-1:45 pm

1 stop7h 05m

Chicago Midway

Thu 12/18

11:00 am-9:35 pm

2 stops9h 35m

$220

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/5

7:25 am-12:34 pm

1 stop6h 09m

Chicago Midway

Mon 12/8

5:29 pm-10:33 pm

1 stop4h 04m

$222

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Mon 12/15

7:40 am-1:00 pm

2 stops6h 20m

Chicago Midway

Thu 12/18

11:00 am-9:35 pm

2 stops9h 35m

$225

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/5

6:45 am-9:54 am

1 stop4h 09m

Chicago Midway

Sun 12/7

5:13 pm-10:33 pm

1 stop4h 20m

$229

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Mon 12/15

7:36 pm-11:47 pm

1 stop5h 11m

Chicago Midway

Thu 1/8

1:28 pm-6:02 pm

1 stop3h 34m

$237

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/19

6:45 am-9:54 am

1 stop4h 09m

Chicago Midway

Wed 1/7

5:31 pm-11:55 pm

1 stop5h 24m

$247

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/5

5:35 am-9:54 am

1 stop5h 19m

Chicago Midway

Sun 12/7

6:00 am-11:15 am

1 stop4h 15m

$254

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 12/13

1:55 pm-8:35 pm

1 stop7h 40m

Chicago Midway

Wed 12/17

7:00 am-2:30 pm

1 stop6h 30m

$258

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 11/25

4:18 pm-10:43 pm

2 stops31h 25m

Chicago Midway

Sun 11/30

5:30 pm-7:23 pm

1 stop24h 53m

$375

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Greenville to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of June is, on average, the cheapest month to fly to Chicago Midway Airport from Greenville, with most prices found around $182. If you are unable to visit Chicago Midway Airport during the month of June, then departing from Greenville during the month April is also very affordable. Most momondo users find prices during this month for around $228.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Greenville. The lowest ticket price found for a Wednesday departure recently was $317. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Greenville because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $498.

Can stopping save me money on Greenville to Chicago Midway Airport flights?

You could potentially save up to 42% on your flight if you consider stops on a Greenville to Chicago Midway Airport flight.

When to book flights from Greenville to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Greenville to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Greenville to Chicago Midway Airport (GSP to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Greenville to Chicago Midway Airport

Direct flights

None
There are no direct flights from Greenville to Chicago Midway Airport. There are no popular flight routes from Greenville to Chicago Midway Airport.
Search flight deals

  • How far is Greenville to Chicago Midway by plane?

    Greenville and Chicago Midway are 559.4 mi apart from one another. 3h 41m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Greenville Airport to Chicago Midway Airport?

    Prices for flights from Greenville Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Greenville Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Greenville Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Greenville Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Greenville to Chicago Midway Airport?

Best airlines flying from Greenville to Chicago Midway Airport

Compare and see reviews for airlines that fly from Greenville to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $180Free CancellationRating
7.9
7,994 reviews
Search Delta flights
SouthwestPriceFrom $232Free CancellationRating
8.0
4,240 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Greenville to Chicago?

Finding the right flight to Chicago from Greenville is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Greenville to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Greenville on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Greenville to Chicago?

momondo helps you find the best flight between Greenville and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Greenville to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Greenville and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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