Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Greenville to Chicago from $89

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 10/15. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Greenville to Chicago

Cheap round-trip flights

Delta Logo
6:35 am - 10:13 amGSP-ORD
4h 38m1 stop
Delta Logo
6:45 am - 2:17 pmORD-GSP
6h 32m1 stop
$206Delta
Find Deal
Thu, Nov 6 - Tue, Nov 11
Southwest Logo
6:05 am - 12:05 pmGSP-MDW
7h 00m2 stops
Southwest Logo
9:05 am - 7:55 pmMDW-GSP
9h 50m2 stops
$207Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
American Airlines Logo
7:20 am - 8:48 amGSP-ORD
2h 28mnonstop
American Airlines Logo
8:00 am - 10:52 amORD-GSP
1h 52mnonstop
$209American Airlines
Find Deal
Fri, Oct 24 - Sun, Oct 26
United Airlines Logo
2:46 pm - 7:58 pmGSP-ORD
6h 12m1 stop
United Airlines Logo
8:50 am - 2:11 pmORD-GSP
4h 21m1 stop
$210United Airlines
Find Deal
Wed, Oct 8 - Thu, Oct 9
Delta Logo
7:36 pm - 12:01 amGSP-ORD
5h 25m1 stop
Delta Logo
12:38 pm - 10:04 pmORD-GSP
8h 26m1 stop
$213Delta
Find Deal
Fri, Dec 5 - Tue, Dec 9
Southwest Logo
4:45 pm - 9:05 pmGSP-MDW
5h 20m1 stop
Southwest Logo
8:50 am - 4:05 pmMDW-GSP
6h 15m1 stop
$213Southwest
Find Deal
Fri, Dec 5 - Tue, Dec 9
Multiple Airlines Logo
9:39 pm - 1:38 pmGSP-ORD
16h 59m1 stop
Multiple Airlines Logo
7:00 am - 8:49 pmORD-GSP
12h 49m1 stop
$219Multiple Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
American Airlines Logo
6:20 am - 11:08 amGSP-ORD
5h 48m1 stop
American Airlines Logo
7:21 pm - 10:11 pmORD-GSP
1h 50mnonstop
$220American Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21
United Airlines Logo
9:35 am - 10:51 amGSP-ORD
2h 16mnonstop
United Airlines Logo
1:50 pm - 4:53 pmORD-GSP
2h 03mnonstop
$229United Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
Multiple Airlines Logo
9:39 pm - 1:38 pmGSP-ORD
16h 59m1 stop
Multiple Airlines Logo
7:00 am - 8:49 pmORD-GSP
12h 49m1 stop
$235Multiple Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15

Delta flights from Greenville to Chicago

Our best Delta deals on Greenville to Chicago flight tickets
Delta
Nov 6
GSP6:35 amGreenville
4h 38m
1 stop
ORD10:13 amChicago O'Hare Intl
Nov 11
ORD6:45 amChicago O'Hare Intl
6h 32m
1 stop
GSP2:17 pmGreenville
$206
Find similar
Delta
Dec 5
GSP7:36 pmGreenville
5h 25m
1 stop
ORD12:01 amChicago O'Hare Intl
Dec 9
ORD12:38 pmChicago O'Hare Intl
8h 26m
1 stop
GSP10:04 pmGreenville
$213
Find similar
Delta
Oct 25
GSP7:05 amGreenville
4h 15m
1 stop
ORD10:20 amChicago O'Hare Intl
Nov 8
ORD6:10 pmChicago O'Hare Intl
4h 45m
1 stop
GSP11:55 pmGreenville
$215
Find similar

American Airlines flights from Greenville to Chicago

Our best American Airlines deals on Greenville to Chicago flight tickets
American Airlines
Oct 24
GSP7:20 amGreenville
2h 28m
ORD8:48 amChicago O'Hare Intl
Oct 26
ORD8:00 amChicago O'Hare Intl
1h 52m
GSP10:52 amGreenville
$209
Find similar
American Airlines
Oct 14
GSP6:20 amGreenville
5h 48m
1 stop
ORD11:08 amChicago O'Hare Intl
Oct 21
ORD7:21 pmChicago O'Hare Intl
1h 50m
GSP10:11 pmGreenville
$220
Find similar
American Airlines
Dec 5
GSP10:59 amGreenville
5h 45m
1 stop
ORD3:44 pmChicago O'Hare Intl
Dec 16
ORD8:14 amChicago O'Hare Intl
1h 58m
GSP11:12 amGreenville
$224
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 September 17, 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

Thu 11/6

6:35 am-10:13 am

1 stop4h 38m

Chicago O'Hare Intl

Tue 11/11

6:45 am-2:17 pm

1 stop6h 32m

$206

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 10/15

6:05 am-12:05 pm

2 stops7h 00m

Chicago Midway

Wed 10/22

9:05 am-7:55 pm

2 stops9h 50m

$207

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 10/24

7:20 am-8:48 am

Nonstop2h 28m

Chicago O'Hare Intl

Sun 10/26

8:00 am-10:52 am

Nonstop1h 52m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Wed 10/8

2:46 pm-7:58 pm

1 stop6h 12m

Chicago O'Hare Intl

Thu 10/9

8:50 am-2:11 pm

1 stop4h 21m

$210

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 12/5

7:36 pm-12:01 am

1 stop5h 25m

Chicago O'Hare Intl

Tue 12/9

12:38 pm-10:04 pm

1 stop8h 26m

$213

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/5

4:45 pm-9:05 pm

1 stop5h 20m

Chicago Midway

Tue 12/9

8:50 am-4:05 pm

1 stop6h 15m

$213

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 12/5

9:39 pm-1:38 pm

1 stop16h 59m

Chicago O'Hare Intl

Mon 12/8

7:00 am-8:49 pm

1 stop12h 49m

$219

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 10/14

6:20 am-11:08 am

1 stop5h 48m

Chicago O'Hare Intl

Tue 10/21

7:21 pm-10:11 pm

Nonstop1h 50m

$220

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 9/30

9:35 am-10:51 am

Nonstop2h 16m

Chicago O'Hare Intl

Sat 10/4

1:50 pm-4:53 pm

Nonstop2h 03m

$229

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 12/12

9:39 pm-1:38 pm

1 stop16h 59m

Chicago O'Hare Intl

Mon 12/15

7:00 am-8:49 pm

1 stop12h 49m

$235

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $244. 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 $385. 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 $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 $281. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $475.

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 $313 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 11% 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 September 2025, prices for Greenville to Chicago flights are approximately 212% 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

$263

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 $263. The best round-trip flight deal from Greenville to Chicago found on momondo in the last 72 hours is $293.
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 04m, 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
7,961 reviews
Search Delta flights
American AirlinesPriceFrom $202Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $212Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
SouthwestPriceFrom $232Free CancellationRating
8.0
4,242 reviews
Search Southwest 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 $352, but momondo users have found United Airlines deals from Greenville to Chicago from as low as $212 round-trip. United Airlines has been scored 7.4/10 in 8,926 reviews.

  • American Airlines Flights From Greenville to Chicago

    American Airlines (7.2/10 from 10,000 reviews) operates around 15 flights from Greenville to Chicago in any given week. The average American Airlines airfare for this route is around $298, 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
Lansing
Portage
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 10/17
Fri 10/24
By creating a price alert you accept our terms of use and privacy policy.

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