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Cheap flights from Greenville to Chicago from $122

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 4/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 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.
Multiple Airlines Logo
8:18 pm - 4:13 pm
GSP
-
MDW
20h 55m
1 stop
Multiple Airlines Logo
8:41 am - 7:38 pm
MDW
-
GSP
9h 57m
1 stop
$234Multiple Airlines
Fri, May 1 - Mon, May 4
Delta Logo
7:30 am - 12:43 pm
GSP
-
MDW
6h 13m
1 stop
Delta Logo
6:23 am - 12:05 pm
MDW
-
GSP
4h 42m
1 stop
$275Delta
Sat, May 2 - Sat, May 9
Multiple Airlines Logo
10:23 am - 7:31 pm
GSP
-
MDW
34h 08m
2 stops
Multiple Airlines Logo
9:14 am - 7:38 pm
MDW
-
GSP
9h 24m
1 stop
$278Multiple Airlines
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
5:05 pm - 8:00 pm
GSP
-
MDW
3h 55m
1 stop
Southwest Logo
10:10 am - 4:20 pm
MDW
-
GSP
5h 10m
2 stops
$280Southwest
Tue, May 12 - Tue, May 19
Southwest Logo
12:50 pm - 4:45 pm
GSP
-
MDW
4h 55m
1 stop
Southwest Logo
3:50 pm - 10:15 pm
MDW
-
GSP
5h 25m
1 stop
$282Southwest
Wed, May 6 - Fri, May 8
Southwest Logo
8:20 am - 3:50 pm
GSP
-
MDW
8h 30m
2 stops
Southwest Logo
10:10 am - 4:20 pm
MDW
-
GSP
5h 10m
2 stops
$285Southwest
Tue, May 12 - Tue, May 19
Southwest Logo
6:45 am - 3:45 pm
GSP
-
MDW
10h 00m
2 stops
Southwest Logo
4:20 pm - 8:40 pm
MDW
-
GSP
3h 20m
1 stop
$286Southwest
Tue, May 26 - Sat, May 30
Southwest Logo
8:20 am - 3:50 pm
GSP
-
MDW
8h 30m
2 stops
Southwest Logo
3:50 pm - 10:15 pm
MDW
-
GSP
5h 25m
1 stop
$287Southwest
Wed, May 6 - Fri, May 8
Southwest Logo
6:25 pm - 11:30 pm
GSP
-
MDW
6h 05m
1 stop
Southwest Logo
11:05 am - 6:30 pm
MDW
-
GSP
6h 25m
1 stop
$289Southwest
Fri, May 1 - Sun, May 10
Southwest Logo
1:55 pm - 7:25 pm
GSP
-
MDW
6h 30m
2 stops
Southwest Logo
1:45 pm - 8:55 pm
MDW
-
GSP
6h 10m
2 stops
$292Southwest
Wed, May 6 - Fri, May 8

Southwest flights from Greenville to Chicago Midway Airport

Our best Southwest deals on Greenville to Chicago Midway Airport flight tickets
Southwest
May 12
GSP5:05 pmGreenville
3h 55m
1 stop
MDW8:00 pmChicago Midway
May 19
MDW10:10 amChicago Midway
5h 10m
2 stops
GSP4:20 pmGreenville
$280
Southwest
May 6
GSP12:50 pmGreenville
4h 55m
1 stop
MDW4:45 pmChicago Midway
May 8
MDW3:50 pmChicago Midway
5h 25m
1 stop
GSP10:15 pmGreenville
$282
Southwest
May 12
GSP8:20 amGreenville
8h 30m
2 stops
MDW3:50 pmChicago Midway
May 19
MDW10:10 amChicago Midway
5h 10m
2 stops
GSP4:20 pmGreenville
$285

Delta flights from Greenville to Chicago Midway Airport

Our best Delta deals on Greenville to Chicago Midway Airport flight tickets
Delta
May 2
GSP7:30 amGreenville
6h 13m
1 stop
MDW12:43 pmChicago Midway
May 9
MDW6:23 amChicago Midway
4h 42m
1 stop
GSP12:05 pmGreenville
$275
Delta
Aug 27
GSP5:45 amGreenville
5h 05m
1 stop
MDW9:50 amChicago Midway
Aug 30
MDW6:00 amChicago Midway
3h 58m
1 stop
GSP10:58 amGreenville
$324
Delta
Apr 9
GSP6:45 amGreenville
4h 11m
1 stop
MDW9:56 amChicago Midway
Apr 13
MDW6:00 amChicago Midway
5h 21m
1 stop
GSP12:21 pmGreenville
$374

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 April 4, 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

Fri 5/1

8:18 pm-4:13 pm

1 stop20h 55m

Chicago Midway

Mon 5/4

8:41 am-7:38 pm

1 stop9h 57m

$234

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 5/2

7:30 am-12:43 pm

1 stop6h 13m

Chicago Midway

Sat 5/9

6:23 am-12:05 pm

1 stop4h 42m

$275

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 4/23

10:23 am-7:31 pm

2 stops34h 08m

Chicago Midway

Mon 4/27

9:14 am-7:38 pm

1 stop9h 24m

$278
Quickest round-trip

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 5/12

5:05 pm-8:00 pm

1 stop3h 55m

Chicago Midway

Tue 5/19

10:10 am-4:20 pm

2 stops5h 10m

$280

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 5/6

12:50 pm-4:45 pm

1 stop4h 55m

Chicago Midway

Fri 5/8

3:50 pm-10:15 pm

1 stop5h 25m

$282

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 5/12

8:20 am-3:50 pm

2 stops8h 30m

Chicago Midway

Tue 5/19

10:10 am-4:20 pm

2 stops5h 10m

$285

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 5/26

6:45 am-3:45 pm

2 stops10h 00m

Chicago Midway

Sat 5/30

4:20 pm-8:40 pm

1 stop3h 20m

$286

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 5/6

8:20 am-3:50 pm

2 stops8h 30m

Chicago Midway

Fri 5/8

3:50 pm-10:15 pm

1 stop5h 25m

$287

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 5/1

6:25 pm-11:30 pm

1 stop6h 05m

Chicago Midway

Sun 5/10

11:05 am-6:30 pm

1 stop6h 25m

$289

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 5/6

1:55 pm-7:25 pm

2 stops6h 30m

Chicago Midway

Fri 5/8

1:45 pm-8:55 pm

2 stops6h 10m

$292

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 17% 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 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
8,383 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
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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