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Greenville

$98+ Cheap flights from Chicago (CHI) to Greenville (GSP)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GSP
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Greenville are usually found in January or July, booked 89 days in advance, depart on a Saturday or Tuesday and return on a Thursday

Cheap flight deals from Chicago to Greenville

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Greenville (GSP). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$219
(American Airlines)

One-way from

$98
(American Airlines)

Popular in

November

Cheapest in

January

Average price

$344

Good round-trip deal

$229 or less

Good one-way deal

$168 or less
Provider with most accurate pricing for Chicago (CHI)-Greenville flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Greenville flights.
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From Chicago (CHI) to Greenville
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One-way flight from Chicago (CHI) to Greenville
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Highest demand for flights based on searches. 12% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Greenville.
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Price to beat on a one-way flight from Chicago (CHI) to Greenville.
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Find flight deals from Chicago to Greenville

Cheapest flights from Chicago to Greenville
Explore the most affordable flight options available from Chicago to Greenville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/74:51 pmORD - GSP
Nonstop1h 53mAmerican Airlines
Fri 11/148:14 pmGSP - ORD
Nonstop2h 16mAmerican Airlines
Deal found 10/12$219
This Southwest deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1912:55 pmMDW - GSP
1 stop5h 45mSouthwest
Thu 11/2010:35 amGSP - MDW
2 stops7h 00mSouthwest
Deal found 10/13$220
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/142:35 pmORD - GSP
1 stop6h 31mDelta
Mon 11/177:59 pmGSP - ORD
1 stop5h 03mDelta
Deal found 10/14$222
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/238:05 amORD - GSP
Nonstop1h 53mAmerican Airlines
Tue 12/28:14 pmGSP - ORD
Nonstop2h 16mAmerican Airlines
Deal found 10/14$226
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/278:15 amORD - GSP
1 stop10h 08mMultiple Airlines
Fri 10/318:03 pmGSP - ORD
1 stop20h 05mMultiple Airlines
Deal found 10/12$228
This American Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/74:51 pmORD - GSP
Nonstop1h 53mAmerican Airlines
Mon 11/108:14 pmGSP - ORD
Nonstop2h 16mAmerican Airlines
Deal found 10/13$229
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:30 amMDW - GSP
2 stops31h 35mMultiple Airlines
Mon 11/173:40 pmGSP - MDW
1 stop9h 50mMultiple Airlines
Deal found 10/13$231
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/198:15 amORD - GSP
Nonstop1h 57mAmerican Airlines
Fri 11/218:00 amGSP - ORD
Nonstop2h 18mAmerican Airlines
Deal found 10/14$231
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:53 pmORD - GSP
Nonstop2h 07mAmerican Airlines
Mon 11/176:19 pmGSP - ORD
1 stop5h 36mAmerican Airlines
Deal found 10/12$233
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1210:52 amORD - GSP
2 stops31h 31mMultiple Airlines
Wed 11/194:16 pmGSP - ORD
1 stop25h 09mMultiple Airlines
Deal found 10/13$234
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:00 amORD - GSP
1 stop3h 43mAmerican Airlines
Sun 12/148:14 pmGSP - ORD
Nonstop2h 16mAmerican Airlines
Deal found 10/14$236
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2210:46 amORD - GSP
1 stop6h 06mDelta
Wed 11/265:35 amGSP - ORD
1 stop4h 06mDelta
Deal found 10/14$237

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Greenville 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, Cheapflights users made 2,558,603 searches. Data last updated October 14, 2025.
Use the filters below to find and compare flights from Chicago to Greenville that are best for you.

Fly from

Chicago

Fly to

Greenville

Route

Depart

Return

Price

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Wed 11/19

12:55 pm-7:40 pm

1 stop5h 45m

Greenville

Thu 11/20

10:35 am-4:35 pm

2 stops7h 00m

$220

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Fri 11/14

2:35 pm-10:06 pm

1 stop6h 31m

Greenville

Mon 11/17

7:59 pm-12:02 am

1 stop5h 03m

$222

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Wed 12/10

2:30 pm-9:42 pm

1 stop6h 12m

Greenville

Sun 12/14

7:36 pm-12:02 am

1 stop5h 26m

$222

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Sun 11/23

8:05 am-10:58 am

Nonstop1h 53m

Greenville

Tue 12/2

8:14 pm-9:30 pm

Nonstop2h 16m

$229

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Fri 12/12

2:30 pm-9:42 pm

1 stop6h 12m

Greenville

Sun 12/14

5:35 am-10:14 am

1 stop5h 39m

$229

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Fri 11/28

8:48 am-11:47 am

Nonstop1h 59m

Greenville

Tue 12/2

9:19 am-10:33 am

Nonstop2h 14m

$233

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Wed 12/10

4:45 pm-11:59 pm

1 stop6h 14m

Greenville

Sun 12/14

8:14 pm-9:30 pm

Nonstop2h 16m

$236

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Sat 10/25

8:45 am-11:46 am

Nonstop2h 01m

Greenville

Wed 10/29

9:10 am-10:24 am

Nonstop2h 14m

$236

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Wed 11/12

8:15 am-11:12 am

Nonstop1h 57m

Greenville

Sun 11/16

6:12 am-7:30 am

Nonstop2h 18m

$238

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Wed 11/19

5:06 pm-8:00 pm

Nonstop1h 54m

Greenville

Fri 11/21

5:15 am-10:42 am

1 stop6h 27m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 37 results
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Compare providers for flights from Chicago to Greenville

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Greenville in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Greenville flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Greenville flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Greenville flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Greenville flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Greenville flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Greenville

Have a flexible travel schedule? Discover the best time to fly to Greenville from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Greenville

How far ahead should I book a flight from Chicago to Greenville?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Greenville. Price data was last updated on October 10, 2025.

Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Greenville. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Greenville?

Currently, February is the cheapest month in which you can book a flight from Chicago to Greenville (average of $51). Flying from Chicago to Greenville in April is currently the most expensive (average of $141). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to GSP?

Find hourly flight availability from Chicago to Greenville. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2025.

It’s optimal to fly from Chicago to Greenville in the evening. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the afternoon.

What is the cheapest day to fly from Chicago to Greenville?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Greenville. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Greenville flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Greenville

Explore weekly flight availability from Chicago to Greenville. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 14, 2025.

The most flights from CHI to GSP are scheduled on a Monday (24 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (22 on average).

Reviews of airlines servicing Greenville

Get insights into the airlines that provide service to Greenville. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Greenville. Reviews last updated October 14, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Chicago to Greenville by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,975 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
8.0
Very good
7,975 reviews
Delta
8.0
Very good
7,975 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,976 reviews
Delta
8.0
Very good
7,975 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,042 reviews
Delta
8.0
Very good
7,975 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Greenville. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Greenville from Chicago?

    Greenville (GSP) is the airport you will fly into if you book a flight from Chicago to Greenville. You should not have trouble finding flights to Greenville from Chicago; the airport handles an average of 23 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 3 airlines have flights to the Greenville airport from Chicago. It is only a 10.4 mi journey from Greenville (GSP) to Greenville’s city center.

  • How long is the flight from Chicago to Greenville?

    For as low as $229, Southwest can have you in Greenville from Chicago in 1h 53m. There are 577 mi between Chicago and Greenville. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Greenville round-trip?

    According to our current data, Delta ($148), American Airlines ($202), and United Airlines ($228) offers the cheapest pricing from Chicago to Greenville. Delta is 52% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Greenville one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $98. Delta flights start at $108 while deals on Southwest start at $108 one-way.

  • What are the most reliable airlines from Chicago to Greenville?

    Consider GoJet (87%), Republic Airways (87%) or United Airlines (87%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Greenville.

  • What are the cheapest flights from Chicago to Greenville?

    Looking at all options, your cheapest flight can be booked for $133. While the most popular route (Chicago O'Hare Intl - Greenville) can be booked for $195 on average, our data indicates $246 when flying from Chicago to Greenville.

  • Can I find deals for flights from Chicago to Greenville that include hotel bookings?

    Yes. In addition to deals on Chicago to Greenville flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Greenville?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Greenville.

  • Can I find deals for business class flights from Chicago to Greenville?

    Yes. Cheapflights offers flight deals from Chicago to Greenville by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Greenville?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Greenville (average of $51). Flying from Chicago to Greenville in April is currently the most expensive (average of $141). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Greenville?

Book flights to Greenville if you plan to visit one of these locations
Simpsonville
Duncan
Seneca
Anderson

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Greenville

Discover the top 3 airlines that operate flights from Chicago to Greenville. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$148Average$276FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$202Average$288FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$228Average$371FlexibilityNo cancel feeOn-time69%

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