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Greenville

$87+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GSP
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Greenville are usually found in July or April, booked 77 days in advance, depart on a Saturday or Tuesday and return on a Saturday

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 September 11, 2025.

Round-trip from

$155
(Southwest)

One-way from

$87
(Southwest)

Popular in

November

Cheapest in

July

Average price

$310

Good round-trip deal

$271 or less

Good one-way deal

$133 or less
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. 10% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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.
Sat 11/85:50 amMDW - GSP
1 stop6h 10mSouthwest
Tue 11/113:05 pmGSP - MDW
1 stop8h 05mSouthwest
Deal found 9/10$155
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/85:50 pmORD - GSP
Nonstop1h 59mUnited Airlines
Tue 11/119:10 amGSP - ORD
Nonstop2h 14mUnited Airlines
Deal found 9/10$195
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 11/275:34 pmMDW - GSP
1 stop5h 21mDelta
Fri 12/57:27 amGSP - MDW
1 stop6h 07mDelta
Deal found 9/9$197
This Delta deal was found by Cheapflights users on 9/10. 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.
Tue 10/79:30 amORD - GSP
1 stop6h 34mDelta
Sun 10/125:30 amGSP - ORD
1 stop4h 02mDelta
Deal found 9/10$197
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/255:17 pmORD - GSP
1 stop24h 29mMultiple Airlines
Mon 9/297:26 pmGSP - ORD
1 stop21h 46mMultiple Airlines
Deal found 9/11$202
This Delta deal was found by Cheapflights users on 9/9. 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 10/46:00 pmORD - GSP
1 stop4h 34mDelta
Sun 10/55:30 amGSP - ORD
1 stop4h 10mDelta
Deal found 9/9$204
This Delta deal was found by Cheapflights users on 9/9. 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.
Tue 11/252:30 pmORD - GSP
1 stop6h 15mDelta
Wed 12/35:35 amGSP - ORD
1 stop4h 10mDelta
Deal found 9/9$206
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:15 pmORD - GSP
Nonstop2h 03mUnited Airlines
Sun 10/53:55 pmGSP - ORD
Nonstop2h 10mUnited Airlines
Deal found 9/9$209
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 10/15:30 amORD - GSP
1 stop4h 54mDelta
Fri 10/36:13 pmGSP - ORD
1 stop6h 41mDelta
Deal found 9/10$212
This Delta deal was found by Cheapflights users on 9/9. 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.
Mon 11/245:34 pmMDW - GSP
1 stop5h 21mDelta
Tue 12/27:27 amGSP - MDW
1 stop6h 07mDelta
Deal found 9/9$213
This Delta deal was found by Cheapflights users on 9/9. 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.
Sun 11/236:03 pmORD - GSP
1 stop4h 52mDelta
Wed 12/35:35 amGSP - ORD
1 stop4h 10mDelta
Deal found 9/9$213
This Delta deal was found by Cheapflights users on 9/8. 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.
Wed 10/86:00 amMDW - GSP
1 stop5h 50mDelta
Sat 10/115:16 pmGSP - MDW
1 stop5h 58mDelta
Deal found 9/8$215

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 September 11, 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

Sat 11/8

5:50 am-1:00 pm

1 stop6h 10m

Greenville

Tue 11/11

3:05 pm-10:10 pm

1 stop8h 05m

$155

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Sat 11/8

5:50 pm-8:49 pm

Nonstop1h 59m

Greenville

Tue 11/11

9:10 am-10:24 am

Nonstop2h 14m

$195

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Sat 10/11

6:10 pm-11:55 pm

1 stop4h 45m

Greenville

Sun 10/12

5:30 am-8:32 am

1 stop4h 02m

$197

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Wed 12/10

5:03 pm-9:41 pm

1 stop3h 38m

Greenville

Sun 12/14

5:35 am-8:42 am

1 stop4h 07m

$197

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Wed 12/24

9:41 am-5:29 pm

1 stop6h 48m

Greenville

Tue 12/30

7:00 am-12:54 pm

1 stop6h 54m

$197

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Sat 10/18

8:45 am-11:46 am

Nonstop2h 01m

Greenville

Sun 10/19

3:55 pm-5:05 pm

Nonstop2h 10m

$202

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Fri 10/3

1:50 pm-4:53 pm

Nonstop2h 03m

Greenville

Sun 10/5

3:55 pm-5:05 pm

Nonstop2h 10m

$209

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Wed 10/1

5:30 am-11:24 am

1 stop4h 54m

Greenville

Fri 10/3

6:13 pm-11:54 pm

1 stop6h 41m

$212

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Sat 11/8

4:09 pm-11:55 pm

1 stop6h 46m

Greenville

Tue 11/11

3:32 pm-10:30 pm

1 stop7h 58m

$215

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Tue 1/6

5:50 am-11:00 am

1 stop4h 10m

Greenville

Sat 1/10

7:15 am-12:41 pm

1 stop6h 26m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 41 results
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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 August 29, 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, August is the cheapest month in which you can book a flight from Chicago to Greenville (average of $322). Flying from Chicago to Greenville in March is currently the most expensive (average of $386). 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 September 11, 2025.

It’s optimal to fly from Chicago to Greenville in the evening. By choosing this option you can save up to 7% on the cost of your flight, compared to a flight in the morning.

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 Friday 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 September 11, 2025.

The most flights from CHI to GSP are scheduled on a Thursday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 September 11, 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
7,960 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 17 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 4 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 $195, Southwest can have you in Greenville from Chicago in 1h 59m. 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 ($209) offers the cheapest pricing from Chicago to Greenville. Delta is 53% cheaper than the average price of flights available within the next 90 days to this destination.

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

    Consider GoJet (100%), Air Canada (78%) or Air New Zealand (78%) 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 $285 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, August is the cheapest month in which you can book a flight from Chicago to Greenville (average of $322). Flying from Chicago to Greenville in March is currently the most expensive (average of $386). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Greenville

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Greenville

Discover the top 4 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$148Average$276FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$202Average$292FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$363FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$278Average$383FlexibilityNo cancel feeOn-time63%

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