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Cheap flights from Greenville to Chicago from $108

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 8/31. 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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Cheap round-trip flights

United Airlines Logo
9:17 am - 10:33 amGSP-ORD
2h 16mnonstop
United Airlines Logo
7:35 pm - 10:46 pmORD-GSP
2h 11mnonstop
$195United Airlines
Find Deal
Sat, Sep 6 - Tue, Sep 9
American Airlines Logo
7:20 am - 8:48 amGSP-ORD
2h 28mnonstop
American Airlines Logo
6:53 pm - 10:00 pmORD-GSP
2h 07mnonstop
$202American Airlines
Find Deal
Sat, Nov 1 - Sun, Nov 2
United Airlines Logo
9:17 am - 10:33 amGSP-ORD
2h 16mnonstop
United Airlines Logo
8:50 am - 2:16 pmORD-GSP
4h 26m1 stop
$205United Airlines
Find Deal
Sat, Sep 6 - Tue, Sep 9
United Airlines Logo
9:35 am - 10:51 amGSP-ORD
2h 16mnonstop
United Airlines Logo
5:50 pm - 9:01 pmORD-GSP
2h 11mnonstop
$209United Airlines
Find Deal
Sat, Aug 23 - Tue, Aug 26
United Airlines Logo
9:35 am - 10:51 amGSP-ORD
2h 16mnonstop
United Airlines Logo
8:50 am - 2:16 pmORD-GSP
4h 26m1 stop
$212United Airlines
Find Deal
Tue, Aug 26 - Tue, Sep 2
Delta Logo
5:20 pm - 10:37 pmGSP-ORD
6h 17m1 stop
Delta Logo
5:45 am - 11:29 amORD-GSP
4h 44m1 stop
$215Delta
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
6:30 am - 9:34 amGSP-MDW
4h 04m1 stop
Delta Logo
1:08 pm - 6:14 pmMDW-GSP
4h 06m1 stop
$215Delta
Find Deal
Tue, Sep 9 - Wed, Sep 17
American Airlines Logo
9:05 am - 4:05 pmGSP-ORD
8h 00m1 stop
American Airlines Logo
6:53 pm - 10:00 pmORD-GSP
2h 07mnonstop
$236American Airlines
Find Deal
Sat, Nov 1 - Sun, Nov 2
Southwest Logo
3:25 pm - 8:25 pmGSP-MDW
6h 00m1 stop
Southwest Logo
9:50 am - 4:30 pmMDW-GSP
5h 40m2 stops
$242Southwest
Find Deal
Wed, Aug 20 - Sat, Sep 13
Southwest Logo
8:00 pm - 12:30 amGSP-MDW
5h 30m1 stop
Southwest Logo
12:30 pm - 7:55 pmMDW-GSP
6h 25m1 stop
$263Southwest
Find Deal
Sun, Oct 12 - Wed, Oct 15

American Airlines flights from Greenville to Chicago

Our best American Airlines deals on Greenville to Chicago flight tickets
American Airlines
Nov 1
GSP7:20 amGreenville
2h 28m
ORD8:48 amChicago O'Hare Intl
Nov 2
ORD6:53 pmChicago O'Hare Intl
2h 07m
GSP10:00 pmGreenville
$202
Find similar
American Airlines
Aug 14
GSP11:25 amGreenville
2h 11m
ORD12:36 pmChicago O'Hare Intl
Aug 18
ORD7:08 pmChicago O'Hare Intl
1h 57m
GSP10:05 pmGreenville
$229
Find similar
American Airlines
Nov 1
GSP9:05 amGreenville
8h 00m
1 stop
ORD4:05 pmChicago O'Hare Intl
Nov 2
ORD6:53 pmChicago O'Hare Intl
2h 07m
GSP10:00 pmGreenville
$236
Find similar

Delta flights from Greenville to Chicago

Our best Delta deals on Greenville to Chicago flight tickets
Delta
Sep 3
GSP5:20 pmGreenville
6h 17m
1 stop
ORD10:37 pmChicago O'Hare Intl
Sep 6
ORD5:45 amChicago O'Hare Intl
4h 44m
1 stop
GSP11:29 amGreenville
$215
Find similar
Delta
Sep 9
GSP6:30 amGreenville
4h 04m
1 stop
MDW9:34 amChicago Midway
Sep 15
MDW6:30 pmChicago Midway
4h 22m
1 stop
GSP11:52 pmGreenville
$222
Find similar
Delta
Aug 20
GSP6:30 amGreenville
6h 46m
1 stop
ORD12:16 pmChicago O'Hare Intl
Aug 25
ORD2:00 pmChicago O'Hare Intl
4h 23m
1 stop
GSP7:23 pmGreenville
$229
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 July 31, 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

Sat 9/6

9:17 am-10:33 am

Nonstop2h 16m

Chicago O'Hare Intl

Tue 9/9

7:35 pm-10:46 pm

Nonstop2h 11m

$195

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 11/1

7:20 am-8:48 am

Nonstop2h 28m

Chicago O'Hare Intl

Sun 11/2

6:53 pm-10:00 pm

Nonstop2h 07m

$202

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 9/6

9:17 am-10:33 am

Nonstop2h 16m

Chicago O'Hare Intl

Tue 9/9

8:50 am-2:16 pm

1 stop4h 26m

$205

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 8/23

9:35 am-10:51 am

Nonstop2h 16m

Chicago O'Hare Intl

Tue 8/26

5:50 pm-9:01 pm

Nonstop2h 11m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 8/26

9:35 am-10:51 am

Nonstop2h 16m

Chicago O'Hare Intl

Tue 9/2

8:50 am-2:16 pm

1 stop4h 26m

$212

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Wed 9/3

5:20 pm-10:37 pm

1 stop6h 17m

Chicago O'Hare Intl

Sat 9/6

5:45 am-11:29 am

1 stop4h 44m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 9/9

6:30 am-9:34 am

1 stop4h 04m

Chicago Midway

Wed 9/17

1:08 pm-6:14 pm

1 stop4h 06m

$215

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 11/1

9:05 am-4:05 pm

1 stop8h 00m

Chicago O'Hare Intl

Sun 11/2

6:53 pm-10:00 pm

Nonstop2h 07m

$236

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 8/20

3:25 pm-8:25 pm

1 stop6h 00m

Chicago Midway

Sat 9/13

9:50 am-4:30 pm

2 stops5h 40m

$242

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sun 10/12

8:00 pm-12:30 am

1 stop5h 30m

Chicago Midway

Wed 10/15

12:30 pm-7:55 pm

1 stop6h 25m

$263

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 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 $263. 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 Friday when prices can be found for as low as $408. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Greenville to Chicago for around $638.

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 $264. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $476.

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 $312 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 $209 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 29% 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 July 2025, prices for Greenville to Chicago flights are approximately 9% 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

$108

Fastest flight time

2h 08m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Greenville in the past 72 hours is $108. The best round-trip flight deal from Greenville to Chicago found on momondo in the last 72 hours is $195.
The fastest flight from Greenville to Chicago takes 2h 08m
Direct flights go from Greenville to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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 08m, 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
8.0
7,981 reviews
Search Delta flights
American AirlinesPriceFrom $202Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $209Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
SouthwestPriceFrom $304Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

  • United Airlines Flights From Greenville to Chicago

    United Airlines operates around 10 flights from Greenville to Chicago every week. The average price of these flights found in the last 72 hours has been $356, but momondo users have found United Airlines deals from Greenville to Chicago from as low as $209 round-trip. United Airlines has been scored 7.4/10 in 8,900 reviews.

  • American Airlines Flights From Greenville to Chicago

    American Airlines (7.2/10 from 10,000 reviews) operates around 14 flights from Greenville to Chicago in any given week. The average American Airlines airfare for this route is around $299, with deals from around $202 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
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