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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 3/9. 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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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 - 1:20 pm
GSP
-
ORD
7h 00m
1 stop
Delta Logo
5:30 am - 11:05 am
ORD
-
GSP
4h 35m
1 stop
$147Delta
Sat, Mar 7 - Wed, Mar 11
Delta Logo
7:20 am - 12:46 pm
GSP
-
MDW
6h 26m
1 stop
Delta Logo
6:00 am - 11:05 am
MDW
-
GSP
4h 05m
1 stop
$147Delta
Sat, Mar 7 - Wed, Mar 11
Delta Logo
6:49 am - 10:17 am
GSP
-
ORD
4h 28m
1 stop
Delta Logo
10:35 am - 5:44 pm
ORD
-
GSP
6h 09m
1 stop
$208Delta
Sat, Feb 21 - Sat, Mar 7
Delta Logo
7:19 am - 12:46 pm
GSP
-
MDW
6h 27m
1 stop
Delta Logo
12:45 pm - 8:19 pm
MDW
-
GSP
6h 34m
1 stop
$208Delta
Tue, Feb 24 - Tue, Mar 3
United Airlines Logo
6:30 am - 7:53 am
GSP
-
ORD
2h 23mnonstop
United Airlines Logo
7:05 am - 10:01 am
ORD
-
GSP
1h 56mnonstop
$209United Airlines
Sat, Mar 7 - Sun, Mar 8
American Airlines Logo
7:40 am - 8:56 am
GSP
-
ORD
2h 16mnonstop
American Airlines Logo
8:50 pm - 11:42 pm
ORD
-
GSP
1h 52mnonstop
$210American Airlines
Sat, Mar 21 - Mon, Mar 23
United Airlines Logo
6:30 am - 7:50 am
GSP
-
ORD
2h 20mnonstop
United Airlines Logo
7:08 am - 10:14 am
ORD
-
GSP
2h 06mnonstop
$212United Airlines
Tue, Jul 7 - Sat, Jul 11
American Airlines Logo
8:14 pm - 9:36 pm
GSP
-
ORD
2h 22mnonstop
American Airlines Logo
8:00 am - 11:01 am
ORD
-
GSP
2h 01mnonstop
$224American Airlines
Thu, Apr 23 - Sun, Apr 26
Southwest Logo
1:55 pm - 7:30 pm
GSP
-
MDW
6h 35m
1 stop
Southwest Logo
12:50 pm - 8:00 pm
MDW
-
GSP
6h 10m
2 stops
$234Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
1:55 pm - 10:15 pm
GSP
-
MDW
9h 20m
2 stops
Southwest Logo
10:10 am - 4:20 pm
MDW
-
GSP
5h 10m
2 stops
$239Southwest
Tue, Apr 7 - Tue, Apr 14

United Airlines flights from Greenville to Chicago

Our best United Airlines deals on Greenville to Chicago flight tickets
United Airlines
Mar 7
GSP6:30 amGreenville
2h 23m
ORD7:53 amChicago O'Hare Intl
Mar 8
ORD7:05 amChicago O'Hare Intl
1h 56m
GSP10:01 amGreenville
$209
United Airlines
Jul 7
GSP6:30 amGreenville
2h 20m
ORD7:50 amChicago O'Hare Intl
Jul 11
ORD7:08 amChicago O'Hare Intl
2h 06m
GSP10:14 amGreenville
$212
United Airlines
Apr 9
GSP7:42 pmGreenville
5h 01m
1 stop
ORD11:43 pmChicago O'Hare Intl
Apr 12
ORD8:40 amChicago O'Hare Intl
2h 04m
GSP11:44 amGreenville
$219

American Airlines flights from Greenville to Chicago

Our best American Airlines deals on Greenville to Chicago flight tickets
American Airlines
Mar 21
GSP7:40 amGreenville
2h 16m
ORD8:56 amChicago O'Hare Intl
Mar 23
ORD8:50 pmChicago O'Hare Intl
1h 52m
GSP11:42 pmGreenville
$210
American Airlines
Apr 23
GSP8:14 pmGreenville
2h 22m
ORD9:36 pmChicago O'Hare Intl
Apr 26
ORD8:00 amChicago O'Hare Intl
2h 01m
GSP11:01 amGreenville
$224
American Airlines
Feb 21
GSP7:29 amGreenville
2h 16m
ORD8:45 amChicago O'Hare Intl
Mar 7
ORD7:22 pmChicago O'Hare Intl
1h 52m
GSP10:14 pmGreenville
$229

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 February 8, 2026.
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

Sat 3/7

7:20 am-1:20 pm

1 stop7h 00m

Chicago O'Hare Intl

Wed 3/11

5:30 am-11:05 am

1 stop4h 35m

$147

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 3/7

7:20 am-12:46 pm

1 stop6h 26m

Chicago Midway

Wed 3/11

6:00 am-11:05 am

1 stop4h 05m

$147

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 2/21

6:49 am-10:17 am

1 stop4h 28m

Chicago O'Hare Intl

Sat 3/7

10:35 am-5:44 pm

1 stop6h 09m

$208

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 2/24

7:19 am-12:46 pm

1 stop6h 27m

Chicago Midway

Tue 3/3

12:45 pm-8:19 pm

1 stop6h 34m

$208

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 3/7

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

Sun 3/8

7:05 am-10:01 am

Nonstop1h 56m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 3/21

7:40 am-8:56 am

Nonstop2h 16m

Chicago O'Hare Intl

Mon 3/23

8:50 pm-11:42 pm

Nonstop1h 52m

$210

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 7/7

6:30 am-7:50 am

Nonstop2h 20m

Chicago O'Hare Intl

Sat 7/11

7:08 am-10:14 am

Nonstop2h 06m

$212

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 4/23

8:14 pm-9:36 pm

Nonstop2h 22m

Chicago O'Hare Intl

Sun 4/26

8:00 am-11:01 am

Nonstop2h 01m

$224

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 4/7

1:55 pm-7:30 pm

1 stop6h 35m

Chicago Midway

Tue 4/14

12:50 pm-8:00 pm

2 stops6h 10m

$234

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 4/7

1:55 pm-10:15 pm

2 stops9h 20m

Chicago Midway

Tue 4/14

10:10 am-4:20 pm

2 stops5h 10m

$239

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 February is, on average, the cheapest month to fly to Chicago from Greenville, with most prices found around $239. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Greenville to Chicago during April average around $261.

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 Thursday when prices can be found for as low as $370. 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 $646.

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 $314. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $826.

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 $304 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?

You could potentially save up to 20% on your flight if you consider stops on a Greenville to Chicago flight.

How have Greenville to Chicago flight prices changed over time?

As of February 2026, prices for Greenville to Chicago flights are approximately 19% 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

$210

Fastest flight time

2h 14m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Greenville in the past 72 hours is $210. The best round-trip flight deal from Greenville to Chicago found on momondo in the last 72 hours is $333.
The fastest flight from Greenville to Chicago takes 2h 14m
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 14m, 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 $107Free CancellationRating
7.9
8,169 reviews
Search Delta flights
American AirlinesPriceFrom $199Free CancellationRating
7.2
11,248 reviews
Search American Airlines flights
United AirlinesPriceFrom $202Free CancellationRating
7.4
9,250 reviews
Search United Airlines flights

  • United Airlines Flights From Greenville to Chicago

    United Airlines operates around 16 flights from Greenville to Chicago every week. The average price of these flights found in the last 72 hours has been $319, 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 9,250 reviews.

  • American Airlines Flights From Greenville to Chicago

    American Airlines (7.2/10 from 11,248 reviews) operates around 11 flights from Greenville to Chicago in any given week. The average American Airlines airfare for this route is around $293, with deals from around $199 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
Schererville
Valparaiso
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?

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