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Cheap flights from Greenville to Chicago from $115

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 3/4. 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
0 bags

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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
7:40 pm - 10:31 pm
GSP
-
MDW
3h 51m
1 stop
Delta Logo
6:00 am - 11:13 am
MDW
-
GSP
4h 13m
1 stop
$229Delta
Fri, Feb 27 - Sun, Mar 1
Southwest Logo
6:25 am - 9:20 am
GSP
-
MDW
3h 55m
1 stop
Southwest Logo
11:35 am - 9:40 pm
MDW
-
GSP
9h 05m
2 stops
$234Southwest
Thu, Apr 2 - Tue, Apr 7
Delta Logo
5:21 pm - 10:28 pm
GSP
-
MDW
6h 07m
1 stop
Delta Logo
5:21 pm - 11:56 pm
MDW
-
GSP
5h 35m
1 stop
$254Delta
Fri, May 1 - Wed, May 6
Southwest Logo
6:25 pm - 12:05 am
GSP
-
MDW
6h 40m
1 stop
Southwest Logo
3:35 pm - 10:40 pm
MDW
-
GSP
6h 05m
1 stop
$260Southwest
Mon, Mar 9 - Wed, Mar 11
Southwest Logo
8:30 am - 1:50 pm
GSP
-
MDW
6h 20m
1 stop
Southwest Logo
1:25 pm - 8:20 pm
MDW
-
GSP
5h 55m
2 stops
$265Southwest
Fri, Feb 27 - Mon, Mar 2
Delta Logo
6:45 am - 9:51 am
GSP
-
MDW
4h 06m
1 stop
Delta Logo
6:00 am - 1:10 pm
MDW
-
GSP
6h 10m
1 stop
$268Delta
Thu, May 7 - Mon, May 11
Southwest Logo
4:25 pm - 11:10 pm
GSP
-
MDW
7h 45m
1 stop
Southwest Logo
10:30 am - 6:00 pm
MDW
-
GSP
6h 30m
1 stop
$269Southwest
Thu, Feb 12 - Sun, Feb 15
Southwest Logo
12:25 pm - 8:10 pm
GSP
-
MDW
8h 45m
2 stops
Southwest Logo
1:20 pm - 10:40 pm
MDW
-
GSP
8h 20m
2 stops
$270Southwest
Mon, Mar 9 - Wed, Mar 11
Southwest Logo
8:00 am - 12:10 pm
GSP
-
MDW
5h 10m
1 stop
Southwest Logo
10:30 am - 8:30 pm
MDW
-
GSP
9h 00m
2 stops
$273Southwest
Fri, Mar 6 - Wed, Mar 11
Southwest Logo
8:30 am - 1:20 pm
GSP
-
MDW
5h 50m
2 stops
Southwest Logo
10:30 am - 6:00 pm
MDW
-
GSP
6h 30m
1 stop
$274Southwest
Thu, Feb 12 - Sun, Feb 15

Southwest flights from Greenville to Chicago Midway Airport

Our best Southwest deals on Greenville to Chicago Midway Airport flight tickets
Southwest
Apr 2
GSP6:25 amGreenville
3h 55m
1 stop
MDW9:20 amChicago Midway
Apr 7
MDW11:35 amChicago Midway
9h 05m
2 stops
GSP9:40 pmGreenville
$234
Southwest
Mar 9
GSP6:25 pmGreenville
6h 40m
1 stop
MDW12:05 amChicago Midway
Mar 11
MDW3:35 pmChicago Midway
6h 05m
1 stop
GSP10:40 pmGreenville
$260
Southwest
Feb 27
GSP8:30 amGreenville
6h 20m
1 stop
MDW1:50 pmChicago Midway
Mar 2
MDW1:25 pmChicago Midway
5h 55m
2 stops
GSP8:20 pmGreenville
$265

Delta flights from Greenville to Chicago Midway Airport

Our best Delta deals on Greenville to Chicago Midway Airport flight tickets
Delta
Feb 27
GSP7:40 pmGreenville
3h 51m
1 stop
MDW10:31 pmChicago Midway
Mar 1
MDW6:00 amChicago Midway
4h 13m
1 stop
GSP11:13 amGreenville
$229
Delta
May 1
GSP5:21 pmGreenville
6h 07m
1 stop
MDW10:28 pmChicago Midway
May 6
MDW5:21 pmChicago Midway
5h 35m
1 stop
GSP11:56 pmGreenville
$254
Delta
May 7
GSP6:45 amGreenville
4h 06m
1 stop
MDW9:51 amChicago Midway
May 11
MDW6:00 amChicago Midway
6h 10m
1 stop
GSP1:10 pmGreenville
$268

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 January 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

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 2/27

7:40 pm-10:31 pm

1 stop3h 51m

Chicago Midway

Sun 3/1

6:00 am-11:13 am

1 stop4h 13m

$229

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 4/2

6:25 am-9:20 am

1 stop3h 55m

Chicago Midway

Tue 4/7

11:35 am-9:40 pm

2 stops9h 05m

$234

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 5/1

5:21 pm-10:28 pm

1 stop6h 07m

Chicago Midway

Wed 5/6

5:21 pm-11:56 pm

1 stop5h 35m

$254

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Mon 3/9

6:25 pm-12:05 am

1 stop6h 40m

Chicago Midway

Wed 3/11

3:35 pm-10:40 pm

1 stop6h 05m

$260

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 2/27

8:30 am-1:50 pm

1 stop6h 20m

Chicago Midway

Mon 3/2

1:25 pm-8:20 pm

2 stops5h 55m

$265

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 5/7

6:45 am-9:51 am

1 stop4h 06m

Chicago Midway

Mon 5/11

6:00 am-1:10 pm

1 stop6h 10m

$268

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 2/12

4:25 pm-11:10 pm

1 stop7h 45m

Chicago Midway

Sun 2/15

10:30 am-6:00 pm

1 stop6h 30m

$269

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Mon 3/9

12:25 pm-8:10 pm

2 stops8h 45m

Chicago Midway

Wed 3/11

1:20 pm-10:40 pm

2 stops8h 20m

$270

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 3/6

8:00 am-12:10 pm

1 stop5h 10m

Chicago Midway

Wed 3/11

10:30 am-8:30 pm

2 stops9h 00m

$273

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 2/12

8:30 am-1:20 pm

2 stops5h 50m

Chicago Midway

Sun 2/15

10:30 am-6:00 pm

1 stop6h 30m

$274

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

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

You could potentially save up to 21% 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 51m

Direct flights

None
The fastest flight from Greenville to Chicago Midway Airport takes 3h 51m
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 51m 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
8,130 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Portage
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Munster
Crown Point
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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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