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Cheap flights from Greenville to Chicago from $93

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 1/19. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
8:22 am - 1:40 pm
GSP
-
ORD
6h 18m1 stop
Delta Logo
5:30 am - 11:03 am
ORD
-
GSP
4h 33m1 stop
$213Delta
Tue, Jan 13 - Wed, Jan 28
Delta Logo
7:20 am - 12:48 pm
GSP
-
MDW
6h 28m1 stop
Delta Logo
1:29 pm - 6:04 pm
MDW
-
GSP
3h 35m1 stop
$213Delta
Wed, Jan 14 - Wed, Jan 21
Delta Logo
5:59 pm - 10:34 pm
GSP
-
ORD
5h 35m1 stop
Delta Logo
11:20 am - 6:14 pm
ORD
-
GSP
5h 54m1 stop
$214Delta
Tue, Jan 20 - Sat, Jan 24
United Airlines Logo
2:55 pm - 6:37 pm
GSP
-
ORD
4h 42m1 stop
United Airlines Logo
7:10 am - 10:16 am
ORD
-
GSP
2h 06mnonstop
$219United Airlines
Fri, Jan 9 - Sun, Jan 11
Multiple Airlines Logo
4:39 pm - 11:09 pm
GSP
-
MDW
7h 30m1 stop
Multiple Airlines Logo
4:21 pm - 3:59 pm
MDW
-
GSP
22h 38m1 stop
$219Multiple Airlines
Fri, Jan 9 - Sun, Jan 11
Multiple Airlines Logo
4:39 pm - 9:12 am
GSP
-
ORD
17h 33m2 stops
Multiple Airlines Logo
8:43 pm - 8:58 am
ORD
-
GSP
11h 15m1 stop
$222Multiple Airlines
Fri, Jan 9 - Sun, Jan 11
American Airlines Logo
7:50 am - 9:10 am
GSP
-
ORD
2h 20mnonstop
American Airlines Logo
5:50 pm - 11:51 pm
ORD
-
GSP
5h 01m1 stop
$226American Airlines
Tue, Jan 20 - Sat, Jan 24
American Airlines Logo
10:32 am - 3:40 pm
GSP
-
ORD
6h 08m1 stop
American Airlines Logo
9:07 pm - 11:59 pm
ORD
-
GSP
1h 52mnonstop
$228American Airlines
Sat, Jan 31 - Sat, Feb 7
Southwest Logo
12:30 pm - 10:40 pm
GSP
-
MDW
11h 10m1 stop
Southwest Logo
8:10 am - 5:35 pm
MDW
-
GSP
8h 25m2 stops
$232Southwest
Thu, Jan 15 - Tue, Jan 20
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
$233Southwest
Thu, Jan 15 - Sun, Jan 18

United Airlines flights from Greenville to Chicago

Our best United Airlines deals on Greenville to Chicago flight tickets
United Airlines
Dec 31
GSP2:50 pmGreenville
5h 02m
1 stop
ORD6:52 pmChicago O'Hare Intl
Jan 24
ORD1:00 pmChicago O'Hare Intl
5h 29m
1 stop
GSP7:29 pmGreenville
$215
Find similar
United Airlines
Dec 24
GSP11:55 amGreenville
2h 19m
ORD1:14 pmChicago O'Hare Intl
Jan 1
ORD2:06 pmChicago O'Hare Intl
1h 55m
GSP5:01 pmGreenville
$222
Find similar
United Airlines
Dec 24
GSP11:55 amGreenville
2h 19m
ORD1:14 pmChicago O'Hare Intl
Jan 1
ORD8:51 amChicago O'Hare Intl
4h 24m
1 stop
GSP2:15 pmGreenville
$232
Find similar

American Airlines flights from Greenville to Chicago

Our best American Airlines deals on Greenville to Chicago flight tickets
American Airlines
Jan 20
GSP7:50 amGreenville
2h 20m
ORD9:10 amChicago O'Hare Intl
Jan 24
ORD5:50 pmChicago O'Hare Intl
5h 01m
1 stop
GSP11:51 pmGreenville
$226
Find similar
American Airlines
Jan 20
GSP5:26 pmGreenville
2h 24m
ORD6:50 pmChicago O'Hare Intl
Jan 24
ORD2:50 pmChicago O'Hare Intl
5h 10m
1 stop
GSP9:00 pmGreenville
$227
Find similar
American Airlines
Jan 31
GSP10:32 amGreenville
6h 08m
1 stop
ORD3:40 pmChicago O'Hare Intl
Feb 7
ORD9:07 pmChicago O'Hare Intl
1h 52m
GSP11:59 pmGreenville
$228
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Greenville to Chicago 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 December 19, 2025.
Use the filters below to find and compare flights from Greenville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 1/13

8:22 am-1:40 pm

1 stop6h 18m

Chicago O'Hare Intl

Wed 1/28

5:30 am-11:03 am

1 stop4h 33m

$213

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 1/14

7:20 am-12:48 pm

1 stop6h 28m

Chicago Midway

Wed 1/21

1:29 pm-6:04 pm

1 stop3h 35m

$213

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 1/20

5:59 pm-10:34 pm

1 stop5h 35m

Chicago O'Hare Intl

Sat 1/24

11:20 am-6:14 pm

1 stop5h 54m

$214

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 1/9

2:55 pm-6:37 pm

1 stop4h 42m

Chicago O'Hare Intl

Sun 1/11

7:10 am-10:16 am

Nonstop2h 06m

$219

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 1/9

4:39 pm-11:09 pm

1 stop7h 30m

Chicago Midway

Sun 1/11

4:21 pm-3:59 pm

1 stop22h 38m

$219

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 1/9

4:39 pm-9:12 am

2 stops17h 33m

Chicago O'Hare Intl

Sun 1/11

8:43 pm-8:58 am

1 stop11h 15m

$222

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 1/20

7:50 am-9:10 am

Nonstop2h 20m

Chicago O'Hare Intl

Sat 1/24

5:50 pm-11:51 pm

1 stop5h 01m

$226

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 1/31

10:32 am-3:40 pm

1 stop6h 08m

Chicago O'Hare Intl

Sat 2/7

9:07 pm-11:59 pm

Nonstop1h 52m

$228

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 1/15

12:30 pm-10:40 pm

1 stop11h 10m

Chicago Midway

Tue 1/20

8:10 am-5:35 pm

2 stops8h 25m

$232

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 1/15

12:30 pm-10:40 pm

1 stop11h 10m

Chicago Midway

Sun 1/18

9:50 am-7:50 pm

1 stop9h 00m

$233

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

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?

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Greenville, with most prices found around $265. If you’re not able to fly to Chicago in November, then April is your next best option. Flight prices from Greenville to Chicago during April average around $269.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $373. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Greenville to Chicago for around $649.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Greenville to Chicago during this time can be as low as $311. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $756.

What is the cheapest Greenville to Chicago flight route?

Fly from Greenville to Chicago O'Hare Intl for the best Greenville - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Greenville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $311 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Greenville for as low as $229 on momondo.

What cabin class options are available on Greenville to Chicago flights?

There are 4 cabin classes available to choose from on Greenville to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Greenville to Chicago flights?

No. A direct flight is the cheapest option for a flight between Greenville to Chicago.

How have Greenville to Chicago flight prices changed over time?

As of December 2025, prices for Greenville to Chicago flights are approximately 59% more expensive when compared to flights at the same time last year.

When to book flights from Greenville to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Greenville to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Greenville to Chicago (GSP to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Greenville to Chicago

Best Price Found

$223

Fastest flight time

2h 02m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Greenville in the past 72 hours is $223. The best round-trip flight deal from Greenville to Chicago found on momondo in the last 72 hours is $298.
The fastest flight from Greenville to Chicago takes 2h 02m
Direct flights go from Greenville to Chicago every day.
There are 3 airports in Chicago. From Greenville there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • How far is Greenville to Chicago by plane?

    A flight from Greenville to Chicago will travel around 561.3 mi. Flights usually cover this in 2h 02m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Greenville Airport to Chicago?

    Prices for flights from Greenville Airport to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Greenville Airport to Chicago?

  • How old do you have to be to fly from Greenville Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Greenville Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Greenville to Chicago?

  • What is the most popular airline from Greenville to Chicago?

Best airlines flying from Greenville to Chicago

Compare and see reviews for airlines that fly from Greenville to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $180Free CancellationRating
7.9
8,010 reviews
Search Delta flights
American AirlinesPriceFrom $201Free CancellationRating
7.2
11,057 reviews
Search American Airlines flights
United AirlinesPriceFrom $202Free CancellationRating
7.4
9,094 reviews
Search United Airlines flights

  • United Airlines Flights From Greenville to Chicago

    United Airlines operates around 18 flights from Greenville to Chicago every week. The average price of these flights found in the last 72 hours has been $330, but momondo users have found United Airlines deals from Greenville to Chicago from as low as $202 round-trip. United Airlines has been scored 7.4/10 in 9,094 reviews.

  • American Airlines Flights From Greenville to Chicago

    American Airlines (7.2/10 from 11,057 reviews) operates around 10 flights from Greenville to Chicago in any given week. The average American Airlines airfare for this route is around $297, with deals from around $201 rare but found on momondo. Referenced prices are for round-trip Greenville to Chicago flight searches in the last 72 hours.

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?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Greenville to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Greenville to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Greenville with this policy.

How can momondo help me find flights from Greenville to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Greenville to Chicago.

I’m not ready to book a flight from Greenville to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Greenville. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport