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Cheap flights from Greenville to Chicago from $134

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 8/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Greenville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:40 am - 2:05 pm
GSP
-
MDW
6h 25m
1 stop
Southwest Logo
8:00 am - 12:30 pm
MDW
-
GSP
3h 30m
1 stop
$294Southwest
Mon, Aug 24 - Mon, Aug 31
Delta Logo
10:04 am - 3:44 pm
GSP
-
MDW
6h 40m
1 stop
Delta Logo
11:35 am - 5:46 pm
MDW
-
GSP
5h 11m
1 stop
$299Delta
Wed, Sep 2 - Wed, Sep 9
Southwest Logo
4:40 pm - 10:20 pm
GSP
-
MDW
6h 40m
2 stops
Southwest Logo
8:00 am - 12:30 pm
MDW
-
GSP
3h 30m
1 stop
$300Southwest
Mon, Aug 24 - Mon, Aug 31
Southwest Logo
8:40 am - 2:55 pm
GSP
-
MDW
7h 15m
2 stops
Southwest Logo
5:00 am - 10:10 am
MDW
-
GSP
4h 10m
1 stop
$304Southwest
Thu, Aug 20 - Sun, Aug 23
Delta Logo
5:20 pm - 10:36 pm
GSP
-
MDW
6h 16m
1 stop
Delta Logo
10:54 am - 4:15 pm
MDW
-
GSP
4h 21m
1 stop
$309Delta
Fri, Aug 21 - Wed, Aug 26
Delta Logo
6:25 pm - 10:44 pm
GSP
-
MDW
5h 19m
1 stop
Delta Logo
6:05 am - 11:08 am
MDW
-
GSP
4h 03m
1 stop
$312Delta
Fri, Sep 11 - Mon, Sep 14
Southwest Logo
6:40 am - 2:50 pm
GSP
-
MDW
9h 10m
2 stops
Southwest Logo
5:00 am - 1:35 pm
MDW
-
GSP
7h 35m
1 stop
$315Southwest
Sat, Oct 10 - Mon, Oct 12
Southwest Logo
6:55 pm - 10:20 pm
GSP
-
MDW
4h 25m
1 stop
Southwest Logo
3:20 pm - 9:35 pm
MDW
-
GSP
5h 15m
1 stop
$319Southwest
Thu, Aug 13 - Thu, Aug 20
Southwest Logo
7:00 am - 11:00 am
GSP
-
MDW
5h 00m
1 stop
Southwest Logo
10:25 am - 6:20 pm
MDW
-
GSP
6h 55m
2 stops
$324Southwest
Thu, Aug 13 - Thu, Aug 20
Southwest Logo
4:40 pm - 10:25 pm
GSP
-
MDW
6h 45m
2 stops
Southwest Logo
11:00 am - 9:40 pm
MDW
-
GSP
9h 40m
1 stop
$325Southwest
Fri, Sep 11 - Mon, Sep 14

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Southwest flights from Greenville to Chicago Midway Airport

Our best Southwest deals on Greenville to Chicago Midway Airport flight tickets
Southwest
Aug 24
GSP8:40 amGreenville
6h 25m
1 stop
MDW2:05 pmChicago Midway
Aug 31
MDW8:00 amChicago Midway
3h 30m
1 stop
GSP12:30 pmGreenville
$294
Southwest
Aug 24
GSP4:40 pmGreenville
6h 40m
2 stops
MDW10:20 pmChicago Midway
Aug 31
MDW8:00 amChicago Midway
3h 30m
1 stop
GSP12:30 pmGreenville
$300
Southwest
Aug 20
GSP4:40 pmGreenville
6h 40m
2 stops
MDW10:20 pmChicago Midway
Aug 23
MDW5:00 amChicago Midway
4h 10m
1 stop
GSP10:10 amGreenville
$304

Delta flights from Greenville to Chicago Midway Airport

Our best Delta deals on Greenville to Chicago Midway Airport flight tickets
Delta
Sep 2
GSP10:04 amGreenville
6h 40m
1 stop
MDW3:44 pmChicago Midway
Sep 9
MDW11:35 amChicago Midway
5h 11m
1 stop
GSP5:46 pmGreenville
$299
Delta
Aug 21
GSP5:20 pmGreenville
6h 16m
1 stop
MDW10:36 pmChicago Midway
Aug 24
MDW5:10 pmChicago Midway
4h 49m
1 stop
GSP10:59 pmGreenville
$309
Delta
Sep 11
GSP6:25 pmGreenville
5h 19m
1 stop
MDW10:44 pmChicago Midway
Sep 14
MDW6:05 amChicago Midway
4h 03m
1 stop
GSP11:08 amGreenville
$312

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 July 31, 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

Price

Cheapest round-trip

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Mon 8/24

8:40 am-2:05 pm

1 stop6h 25m

Chicago Midway

Mon 8/31

8:00 am-12:30 pm

1 stop3h 30m

$294

GreenvilleChicago

GSP - MDW

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

$299

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Mon 8/24

4:40 pm-10:20 pm

2 stops6h 40m

Chicago Midway

Mon 8/31

8:00 am-12:30 pm

1 stop3h 30m

$300

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 8/20

8:40 am-2:55 pm

2 stops7h 15m

Chicago Midway

Sun 8/23

5:00 am-10:10 am

1 stop4h 10m

$304

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 8/21

5:20 pm-10:36 pm

1 stop6h 16m

Chicago Midway

Wed 8/26

10:54 am-4:15 pm

1 stop4h 21m

$309
Quickest round-trip

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 9/11

6:25 pm-10:44 pm

1 stop5h 19m

Chicago Midway

Mon 9/14

6:05 am-11:08 am

1 stop4h 03m

$312

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 10/10

6:40 am-2:50 pm

2 stops9h 10m

Chicago Midway

Mon 10/12

5:00 am-1:35 pm

1 stop7h 35m

$315

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 8/13

6:55 pm-10:20 pm

1 stop4h 25m

Chicago Midway

Thu 8/20

3:20 pm-9:35 pm

1 stop5h 15m

$319

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 8/13

7:00 am-11:00 am

1 stop5h 00m

Chicago Midway

Thu 8/20

10:25 am-6:20 pm

2 stops6h 55m

$324

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 9/11

4:40 pm-10:25 pm

2 stops6h 45m

Chicago Midway

Mon 9/14

11:00 am-9:40 pm

1 stop9h 40m

$325

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 airline that flies from Greenville to Chicago Midway?

Delta and Southwest are the most popular carriers operating from Greenville to Chicago Midway

What airlines fly to Chicago Midway Airport?

Southwest, Allegiant Air and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Greenville according to our data. Southwest is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

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

Fastest flight time

3h 49m

Direct flights

None
The fastest flight from Greenville to Chicago Midway Airport takes 3h 49m
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

Frequently asked questions about flying from Greenville to Chicago Midway Airport

  • How far is Greenville to Chicago Midway by plane?

    Greenville and Chicago Midway are 559.4 mi apart from one another. 3h 49m 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 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Benton Harbor
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Schererville
Munster
Chesterton
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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.

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