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Cheap flights from Greenville to Chicago from $90

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 12/5. 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

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American Airlines Logo
6:00 am - 7:13 amGSP-ORD
2h 13mnonstop
American Airlines Logo
8:14 am - 11:12 amORD-GSP
1h 58mnonstop
$195American Airlines
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Sat, Dec 6 - Tue, Dec 9
United Airlines Logo
5:36 pm - 6:55 pmGSP-ORD
2h 19mnonstop
United Airlines Logo
2:06 pm - 5:01 pmORD-GSP
1h 55mnonstop
$202United Airlines
Find Deal
Wed, Dec 24 - Sun, Dec 28
United Airlines Logo
10:00 am - 2:25 pmGSP-ORD
5h 25m1 stop
United Airlines Logo
1:55 pm - 4:53 pmORD-GSP
1h 58mnonstop
$205United Airlines
Find Deal
Tue, Dec 9 - Sat, Dec 13
Multiple Airlines Logo
5:17 pm - 10:36 pmGSP-ORD
6h 19m1 stop
Multiple Airlines Logo
6:48 am - 9:20 pmORD-GSP
13h 32m1 stop
$208Multiple Airlines
Find Deal
Thu, Nov 27 - Mon, Dec 1
American Airlines Logo
6:00 am - 7:13 amGSP-ORD
2h 13mnonstop
American Airlines Logo
8:05 am - 11:01 amORD-GSP
1h 56mnonstop
$209American Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
United Airlines Logo
12:23 pm - 1:35 pmGSP-ORD
2h 12mnonstop
United Airlines Logo
1:00 pm - 7:10 pmORD-GSP
5h 10m1 stop
$212United Airlines
Find Deal
Mon, Nov 24 - Thu, Nov 27
Delta Logo
5:35 am - 8:41 amGSP-ORD
4h 06m1 stop
Delta Logo
1:14 pm - 7:13 pmORD-GSP
4h 59m1 stop
$215Delta
Find Deal
Mon, Nov 24 - Thu, Nov 27
Delta Logo
5:35 am - 9:52 amGSP-MDW
5h 17m1 stop
Delta Logo
5:34 pm - 11:45 pmMDW-GSP
5h 11m1 stop
$215Delta
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Mon, Nov 24 - Thu, Nov 27
Southwest Logo
4:45 pm - 9:05 pmGSP-MDW
5h 20m1 stop
Southwest Logo
9:35 am - 9:35 pmMDW-GSP
11h 00m1 stop
$254Southwest
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Thu, Dec 11 - Sun, Dec 14
Southwest Logo
10:05 am - 2:55 pmGSP-MDW
5h 50m1 stop
Southwest Logo
1:15 pm - 7:50 pmMDW-GSP
5h 35m1 stop
$258Southwest
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Tue, Jan 20 - Fri, Jan 23

United Airlines flights from Greenville to Chicago

Our best United Airlines deals on Greenville to Chicago flight tickets
United Airlines
Dec 24
GSP5:36 pmGreenville
2h 19m
ORD6:55 pmChicago O'Hare Intl
Dec 28
ORD2:06 pmChicago O'Hare Intl
1h 55m
GSP5:01 pmGreenville
$202
Find similar
United Airlines
Dec 9
GSP10:00 amGreenville
5h 25m
1 stop
ORD2:25 pmChicago O'Hare Intl
Dec 13
ORD1:55 pmChicago O'Hare Intl
1h 58m
GSP4:53 pmGreenville
$205
Find similar
United Airlines
Nov 24
GSP12:23 pmGreenville
2h 12m
ORD1:35 pmChicago O'Hare Intl
Nov 27
ORD1:00 pmChicago O'Hare Intl
5h 10m
1 stop
GSP7:10 pmGreenville
$212
Find similar

American Airlines flights from Greenville to Chicago

Our best American Airlines deals on Greenville to Chicago flight tickets
American Airlines
Dec 6
GSP6:00 amGreenville
2h 13m
ORD7:13 amChicago O'Hare Intl
Dec 9
ORD8:14 amChicago O'Hare Intl
1h 58m
GSP11:12 amGreenville
$195
Find similar
American Airlines
Dec 5
GSP6:00 amGreenville
2h 13m
ORD7:13 amChicago O'Hare Intl
Dec 7
ORD8:05 amChicago O'Hare Intl
1h 56m
GSP11:01 amGreenville
$209
Find similar
American Airlines
Jan 27
GSP5:26 pmGreenville
2h 24m
ORD6:50 pmChicago O'Hare Intl
Jan 30
ORD9:07 pmChicago O'Hare Intl
1h 52m
GSP11:59 pmGreenville
$231
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 November 3, 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 12/6

6:00 am-7:13 am

Nonstop2h 13m

Chicago O'Hare Intl

Tue 12/9

8:14 am-11:12 am

Nonstop1h 58m

$195

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Wed 12/24

5:36 pm-6:55 pm

Nonstop2h 19m

Chicago O'Hare Intl

Sun 12/28

2:06 pm-5:01 pm

Nonstop1h 55m

$202

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 12/9

10:00 am-2:25 pm

1 stop5h 25m

Chicago O'Hare Intl

Sat 12/13

1:55 pm-4:53 pm

Nonstop1h 58m

$205

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 11/27

5:17 pm-10:36 pm

1 stop6h 19m

Chicago O'Hare Intl

Mon 12/1

6:48 am-9:20 pm

1 stop13h 32m

$208

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 12/5

6:00 am-7:13 am

Nonstop2h 13m

Chicago O'Hare Intl

Sun 12/7

8:05 am-11:01 am

Nonstop1h 56m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Mon 11/24

12:23 pm-1:35 pm

Nonstop2h 12m

Chicago O'Hare Intl

Thu 11/27

1:00 pm-7:10 pm

1 stop5h 10m

$212

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Mon 11/24

5:35 am-8:41 am

1 stop4h 06m

Chicago O'Hare Intl

Thu 11/27

1:14 pm-7:13 pm

1 stop4h 59m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Mon 11/24

5:35 am-9:52 am

1 stop5h 17m

Chicago Midway

Thu 11/27

5:34 pm-11:45 pm

1 stop5h 11m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 12/11

4:45 pm-9:05 pm

1 stop5h 20m

Chicago Midway

Sun 12/14

9:35 am-9:35 pm

1 stop11h 00m

$254

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 1/20

10:05 am-2:55 pm

1 stop5h 50m

Chicago Midway

Fri 1/23

1:15 pm-7:50 pm

1 stop5h 35m

$258

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 $267. 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 Thursday when prices can be found for as low as $381. 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 $639.

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 $289. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $570.

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 $310 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 37% 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 November 2025, prices for Greenville to Chicago flights are approximately 50% 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

$253

Fastest flight time

2h 02m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Greenville in the past 72 hours is $253. The best round-trip flight deal from Greenville to Chicago found on momondo in the last 72 hours is $294.
The fastest flight from Greenville to Chicago takes 2h 02m
Direct flights go from Greenville to Chicago every day.
There is 1 airport near Chicago: 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 11m, 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
8,002 reviews
Search Delta flights
American AirlinesPriceFrom $201Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
United AirlinesPriceFrom $209Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights

  • United Airlines Flights From Greenville to Chicago

    United Airlines operates around 19 flights from Greenville to Chicago every week. The average price of these flights found in the last 72 hours has been $340, 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 8,997 reviews.

  • American Airlines Flights From Greenville to Chicago

    American Airlines (7.2/10 from 11,038 reviews) operates around 12 flights from Greenville to Chicago in any given week. The average American Airlines airfare for this route is around $296, 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
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