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Cheap flights from Greenville to Chicago from $145

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 6/16. 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
5:44 am - 10:09 am
GSP
-
MDW
5h 25m
1 stop
Delta Logo
1:26 pm - 6:15 pm
MDW
-
GSP
3h 49m
1 stop
$282Delta
Tue, Jun 23 - Tue, Jun 30
Southwest Logo
7:50 pm - 11:10 pm
GSP
-
MDW
4h 20m
1 stop
Southwest Logo
11:50 am - 8:15 pm
MDW
-
GSP
7h 25m
2 stops
$287Southwest
Tue, Jun 23 - Tue, Jun 30
Delta Logo
8:49 am - 11:51 am
GSP
-
MDW
4h 02m
1 stop
Delta Logo
6:05 am - 10:40 am
MDW
-
GSP
3h 35m
1 stop
$289Delta
Fri, Aug 7 - Sun, Aug 9
Southwest Logo
7:00 am - 10:55 am
GSP
-
MDW
4h 55m
1 stop
Southwest Logo
8:50 am - 4:45 pm
MDW
-
GSP
6h 55m
2 stops
$294Southwest
Tue, Sep 1 - Tue, Sep 8
Delta Logo
7:15 am - 12:33 pm
GSP
-
MDW
6h 18m
1 stop
Delta Logo
5:25 pm - 11:37 pm
MDW
-
GSP
5h 12m
1 stop
$295Delta
Tue, Oct 6 - Tue, Oct 6
Southwest Logo
7:30 pm - 12:20 am
GSP
-
MDW
5h 50m
1 stop
Southwest Logo
7:25 am - 1:10 pm
MDW
-
GSP
4h 45m
1 stop
$297Southwest
Sun, Jun 21 - Tue, Jun 30
Southwest Logo
11:00 am - 7:10 pm
GSP
-
MDW
9h 10m
2 stops
Southwest Logo
8:50 am - 4:45 pm
MDW
-
GSP
6h 55m
2 stops
$299Southwest
Tue, Sep 1 - Tue, Sep 8
Southwest Logo
7:30 pm - 12:20 am
GSP
-
MDW
5h 50m
1 stop
Southwest Logo
11:50 am - 8:15 pm
MDW
-
GSP
7h 25m
2 stops
$302Southwest
Sun, Jun 21 - Tue, Jun 30
Southwest Logo
6:50 pm - 9:55 pm
GSP
-
MDW
4h 05m
1 stop
Southwest Logo
5:05 pm - 10:50 pm
MDW
-
GSP
4h 45m
1 stop
$304Southwest
Thu, Jun 18 - Fri, Jun 19
Southwest Logo
1:20 pm - 8:10 pm
GSP
-
MDW
7h 50m
2 stops
Southwest Logo
8:00 am - 12:30 pm
MDW
-
GSP
3h 30m
1 stop
$305Southwest
Wed, Aug 5 - Mon, Aug 10

Delta flights from Greenville to Chicago Midway Airport

Our best Delta deals on Greenville to Chicago Midway Airport flight tickets
Delta
Jun 23
GSP5:44 amGreenville
5h 25m
1 stop
MDW10:09 amChicago Midway
Jun 30
MDW1:26 pmChicago Midway
3h 49m
1 stop
GSP6:15 pmGreenville
$282
Delta
Aug 7
GSP8:49 amGreenville
4h 02m
1 stop
MDW11:51 amChicago Midway
Aug 10
MDW1:27 pmChicago Midway
3h 48m
1 stop
GSP6:15 pmGreenville
$289
Delta
Oct 6
GSP7:15 amGreenville
6h 18m
1 stop
MDW12:33 pmChicago Midway
Oct 6
MDW5:25 pmChicago Midway
5h 12m
1 stop
GSP11:37 pmGreenville
$295

Southwest flights from Greenville to Chicago Midway Airport

Our best Southwest deals on Greenville to Chicago Midway Airport flight tickets
Southwest
May 27
GSP5:05 pmGreenville
6h 10m
1 stop
MDW10:15 pmChicago Midway
May 29
MDW3:50 pmChicago Midway
5h 45m
1 stop
GSP10:35 pmGreenville
$275
Southwest
May 27
GSP12:50 pmGreenville
4h 55m
1 stop
MDW4:45 pmChicago Midway
May 29
MDW9:00 amChicago Midway
7h 50m
2 stops
GSP5:50 pmGreenville
$280
Southwest
Jun 23
GSP7:50 pmGreenville
4h 20m
1 stop
MDW11:10 pmChicago Midway
Jun 30
MDW11:50 amChicago Midway
7h 25m
2 stops
GSP8:15 pmGreenville
$287

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 May 25, 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

Tue 6/23

5:44 am-10:09 am

1 stop5h 25m

Chicago Midway

Tue 6/30

1:26 pm-6:15 pm

1 stop3h 49m

$282

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 6/23

7:50 pm-11:10 pm

1 stop4h 20m

Chicago Midway

Tue 6/30

11:50 am-8:15 pm

2 stops7h 25m

$287
Quickest round-trip

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 8/7

8:49 am-11:51 am

1 stop4h 02m

Chicago Midway

Sun 8/9

6:05 am-10:40 am

1 stop3h 35m

$289

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 9/1

7:00 am-10:55 am

1 stop4h 55m

Chicago Midway

Tue 9/8

8:50 am-4:45 pm

2 stops6h 55m

$294

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 10/6

7:15 am-12:33 pm

1 stop6h 18m

Chicago Midway

Tue 10/6

5:25 pm-11:37 pm

1 stop5h 12m

$295

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sun 6/21

7:30 pm-12:20 am

1 stop5h 50m

Chicago Midway

Tue 6/30

7:25 am-1:10 pm

1 stop4h 45m

$297

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 9/1

11:00 am-7:10 pm

2 stops9h 10m

Chicago Midway

Tue 9/8

8:50 am-4:45 pm

2 stops6h 55m

$299

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sun 6/21

7:30 pm-12:20 am

1 stop5h 50m

Chicago Midway

Tue 6/30

11:50 am-8:15 pm

2 stops7h 25m

$302

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 6/18

6:50 pm-9:55 pm

1 stop4h 05m

Chicago Midway

Fri 6/19

5:05 pm-10:50 pm

1 stop4h 45m

$304

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 8/5

1:20 pm-8:10 pm

2 stops7h 50m

Chicago Midway

Mon 8/10

8:00 am-12:30 pm

1 stop3h 30m

$305

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 typical price of a round-trip flight between Greenville and Chicago Midway Airport?

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

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Greenville, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Greenville during the month November is also very affordable. Most momondo users find prices during this month for around $0.

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

You could potentially save up to 38% 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

Fastest flight time

3h 55m

Direct flights

None
The fastest flight from Greenville to Chicago Midway Airport takes 3h 55m
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 55m 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
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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