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Cheap flights from Greenville to Chicago from $130

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 1/8. 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
7:20 am - 12:49 pm
GSP
-
MDW
6h 29m1 stop
Delta Logo
6:25 am - 11:08 am
MDW
-
GSP
3h 43m1 stop
$215Delta
mié., ene. 21 - sáb., ene. 24
Delta Logo
7:20 am - 12:48 pm
GSP
-
MDW
6h 28m1 stop
Delta Logo
11:21 am - 4:53 pm
MDW
-
GSP
4h 32m1 stop
$222Delta
vie., ene. 9 - sáb., ene. 17
Southwest Logo
10:05 am - 2:55 pm
GSP
-
MDW
5h 50m1 stop
Southwest Logo
8:40 am - 3:35 pm
MDW
-
GSP
5h 55m1 stop
$237Southwest
mié., ene. 21 - sáb., ene. 24
Southwest Logo
10:50 am - 1:40 pm
GSP
-
MDW
3h 50m1 stop
Southwest Logo
9:50 am - 7:50 pm
MDW
-
GSP
9h 00m1 stop
$242Southwest
sáb., ene. 17 - dom., ene. 18
Southwest Logo
10:05 am - 6:50 pm
GSP
-
MDW
9h 45m2 stops
Southwest Logo
12:50 pm - 7:50 pm
MDW
-
GSP
6h 00m2 stops
$247Southwest
mié., ene. 21 - sáb., ene. 24
Southwest Logo
7:45 am - 1:40 pm
GSP
-
MDW
6h 55m2 stops
Southwest Logo
9:50 am - 7:50 pm
MDW
-
GSP
9h 00m1 stop
$248Southwest
sáb., ene. 17 - dom., ene. 18
Southwest Logo
12:30 pm - 10:40 pm
GSP
-
MDW
11h 10m1 stop
Southwest Logo
9:50 am - 7:50 pm
MDW
-
GSP
9h 00m1 stop
$269Southwest
vie., ene. 16 - dom., ene. 18
Delta Logo
7:20 am - 12:48 pm
GSP
-
MDW
6h 28m1 stop
Delta Logo
6:45 am - 2:15 pm
MDW
-
GSP
6h 30m1 stop
$277Delta
sáb., ene. 17 - dom., ene. 18
Delta Logo
7:15 am - 12:30 pm
GSP
-
MDW
6h 15m1 stop
Delta Logo
6:00 am - 1:10 pm
MDW
-
GSP
6h 10m1 stop
$287Delta
sáb., may. 9 - lun., may. 11
Delta Logo
5:45 am - 9:05 am
GSP
-
MDW
4h 20m1 stop
Delta Logo
11:21 am - 6:55 pm
MDW
-
GSP
6h 34m1 stop
$294Delta
dom., dic. 28 - mié., ene. 7

Delta flights from Greenville to Chicago Midway Airport

Our best Delta deals on Greenville to Chicago Midway Airport flight tickets
Delta
Jan 17
GSP7:20 amGreenville
6h 28m
1 stop
MDW12:48 pmChicago Midway
Jan 18
MDW6:45 amChicago Midway
6h 30m
1 stop
GSP2:15 pmGreenville
$277
Find similar
Delta
May 9
GSP7:15 amGreenville
6h 15m
1 stop
MDW12:30 pmChicago Midway
May 11
MDW6:00 amChicago Midway
6h 10m
1 stop
GSP1:10 pmGreenville
$287
Find similar
Delta
Dec 28
GSP5:45 amGreenville
4h 20m
1 stop
MDW9:05 amChicago Midway
Jan 8
MDW11:21 amChicago Midway
6h 34m
1 stop
GSP6:55 pmGreenville
$294
Find similar

Southwest flights from Greenville to Chicago Midway Airport

Our best Southwest deals on Greenville to Chicago Midway Airport flight tickets
Southwest
Jan 26
GSP10:05 amGreenville
5h 50m
1 stop
MDW2:55 pmChicago Midway
Jan 28
MDW1:15 pmChicago Midway
5h 35m
1 stop
GSP7:50 pmGreenville
$237
Find similar
Southwest
Jan 17
GSP10:50 amGreenville
3h 50m
1 stop
MDW1:40 pmChicago Midway
Jan 18
MDW9:50 amChicago Midway
9h 00m
1 stop
GSP7:50 pmGreenville
$242
Find similar
Southwest
Jan 26
GSP10:05 amGreenville
9h 45m
2 stops
MDW6:50 pmChicago Midway
Jan 28
MDW8:10 amChicago Midway
8h 25m
2 stops
GSP5:35 pmGreenville
$247
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 diciembre 15, 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

mié. 1/21

7:20 am-12:49 pm

1 stop6h 29m

Chicago Midway

sáb. 1/24

6:25 am-11:08 am

1 stop3h 43m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

vie. 1/9

7:20 am-12:48 pm

1 stop6h 28m

Chicago Midway

sáb. 1/17

11:21 am-4:53 pm

1 stop4h 32m

$222

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

mié. 1/21

10:05 am-2:55 pm

1 stop5h 50m

Chicago Midway

sáb. 1/24

8:40 am-3:35 pm

1 stop5h 55m

$237

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

sáb. 1/17

10:50 am-1:40 pm

1 stop3h 50m

Chicago Midway

dom. 1/18

9:50 am-7:50 pm

1 stop9h 00m

$242

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

mié. 1/21

10:05 am-6:50 pm

2 stops9h 45m

Chicago Midway

sáb. 1/24

12:50 pm-7:50 pm

2 stops6h 00m

$247

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

sáb. 1/17

7:45 am-1:40 pm

2 stops6h 55m

Chicago Midway

dom. 1/18

9:50 am-7:50 pm

1 stop9h 00m

$248

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

vie. 1/16

12:30 pm-10:40 pm

1 stop11h 10m

Chicago Midway

dom. 1/18

9:50 am-7:50 pm

1 stop9h 00m

$269

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

sáb. 1/17

7:20 am-12:48 pm

1 stop6h 28m

Chicago Midway

dom. 1/18

6:45 am-2:15 pm

1 stop6h 30m

$277

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

sáb. 5/9

7:15 am-12:30 pm

1 stop6h 15m

Chicago Midway

lun. 5/11

6:00 am-1:10 pm

1 stop6h 10m

$287

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

dom. 12/28

5:45 am-9:05 am

1 stop4h 20m

Chicago Midway

mié. 1/7

11:21 am-6:55 pm

1 stop6h 34m

$294

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 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 28% 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

  • 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 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
8,008 reviews
Search Delta 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
Valparaiso
Schererville
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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mié. 1/14
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