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Greenville

$93+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GSP
Aug 12 — Aug 191
Wed 8/12
Wed 8/19
1 adult, Economy
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Find cheap flights from Chicago to Greenville with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to Greenville are usually found in January or February, booked 89 days in advance, depart on a Saturday or Tuesday and return on a Thursday

Cheap 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 July 13, 2026.

This Southwest deal was found by Cheapflights users on 7/10. 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.
Mon 8/248:00 am
MDW
-
GSP
1 stop3h 30m
Southwest
Mon 8/317:00 am
GSP
-
MDW
1 stop5h 00m
Southwest
Deal found 7/10$189
This Southwest deal was found by Cheapflights users on 7/10. 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.
Tue 8/46:30 am
MDW
-
GSP
2 stops9h 15m
Southwest
Wed 8/55:30 pm
GSP
-
MDW
1 stop3h 40m
Southwest
Deal found 7/10$199
This Southwest deal was found by Cheapflights users on 7/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:55 am
MDW
-
GSP
1 stop5h 35m
Southwest
Mon 8/174:40 pm
GSP
-
MDW
1 stop5h 20m
Southwest
Deal found 7/8$203
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:05 am
ORD
-
GSP
2 stops10h 28m
Multiple Airlines
Mon 8/315:34 pm
GSP
-
ORD
1 stop20h 16m
Multiple Airlines
Deal found 7/10$203
This Southwest deal was found by Cheapflights users on 7/10. 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.
Thu 8/278:45 am
MDW
-
GSP
2 stops6h 20m
Southwest
Mon 8/318:40 am
GSP
-
MDW
2 stops7h 15m
Southwest
Deal found 7/10$209
This Southwest deal was found by Cheapflights users on 7/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:25 am
MDW
-
GSP
2 stops9h 55m
Southwest
Sat 8/1512:55 pm
GSP
-
MDW
1 stop8h 35m
Southwest
Deal found 7/9$214
This Southwest deal was found by Cheapflights users on 7/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:55 am
MDW
-
GSP
1 stop5h 35m
Southwest
Mon 8/104:40 pm
GSP
-
MDW
1 stop5h 20m
Southwest
Deal found 7/9$217
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:13 pm
ORD
-
GSP
1 stop13h 15m
Multiple Airlines
Thu 8/203:43 pm
GSP
-
ORD
1 stop22h 37m
Multiple Airlines
Deal found 7/9$222
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:05 am
ORD
-
GSP
2 stops10h 34m
Multiple Airlines
Mon 8/3112:06 pm
GSP
-
ORD
1 stop25h 44m
Multiple Airlines
Deal found 7/10$230
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:05 am
ORD
-
GSP
2 stops10h 28m
Multiple Airlines
Thu 8/278:37 am
GSP
-
ORD
1 stop29h 13m
Multiple Airlines
Deal found 7/10$231

Find 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 July 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$189
(Southwest)

One-way from

$93
(Southwest)

Popular in

May

Cheapest in

January

Average price

$311

Good round-trip deal

$274 or less

Good one-way deal

$253 or less
Provider with most accurate pricing for Chicago (CHI)-Greenville flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Greenville flights.
Search Deals
From Chicago (CHI) to Greenville
Search Deals
One-way flight from Chicago (CHI) to Greenville
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Greenville.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Greenville.
Search Deals

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 July 13, 2026.
Use the filters below to find and compare flights from Chicago to Greenville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Mon 8/24

8:00 am-12:30 pm

1 stop3h 30m

Greenville

Mon 8/31

7:00 am-11:00 am

1 stop5h 00m

$189

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Thu 8/27

3:20 pm-9:35 pm

1 stop5h 15m

Greenville

Mon 8/31

8:40 am-2:55 pm

2 stops7h 15m

$199

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Thu 8/13

5:55 am-12:30 pm

1 stop5h 35m

Greenville

Mon 8/17

1:05 pm-7:30 pm

2 stops7h 25m

$208

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Fri 8/7

5:55 am-12:30 pm

1 stop5h 35m

Greenville

Mon 8/10

4:40 pm-9:00 pm

1 stop5h 20m

$217

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Wed 8/5

6:30 am-4:45 pm

2 stops9h 15m

Greenville

Fri 8/7

4:40 pm-10:20 pm

2 stops6h 40m

$240

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Thu 8/27

8:45 am-4:05 pm

2 stops6h 20m

Greenville

Sun 8/30

10:45 am-2:55 pm

2 stops5h 10m

$256

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Fri 8/21

1:25 pm-6:13 pm

1 stop3h 48m

Greenville

Sun 8/23

6:55 am-9:59 am

1 stop4h 04m

$289

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Sat 8/29

6:11 am-12:41 pm

1 stop5h 30m

Greenville

Sat 9/5

5:20 pm-10:36 pm

1 stop6h 16m

$289

ChicagoGreenville

MDW - GSP

MDWGSP

Chicago Midway

Wed 7/29

6:00 am-12:14 pm

1 stop5h 14m

Greenville

Wed 8/5

7:15 am-12:39 pm

1 stop6h 24m

$289

ChicagoGreenville

ORD - GSP

ORDGSP

Chicago O'Hare Intl

Sat 10/10

5:30 am-1:08 pm

1 stop6h 38m

Greenville

Sat 10/17

5:40 am-9:24 am

1 stop4h 44m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/10

Showing 1-10 of 39 resultsSorted by cheapest first
1
2
3
4

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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

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

Currently, June is the cheapest month in which you can book a flight from Chicago to Greenville (average of $146). Flying from Chicago to Greenville in August is currently the most expensive (average of $209). 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 July 13, 2026.

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

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 July 13, 2026.

The most flights from CHI to GSP are scheduled on a Monday (21 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (19 on average).

How much does it cost to fly round-trip from Chicago to Greenville?

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

Booking 88 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 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 July 11, 2026.

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

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 July 13, 2026.
Get a feel of what it's like to fly with 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.
United Airlines
7.4
Good
9,983 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.7

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
9,983 reviews
United Airlines
7.4
Good
9,983 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.7

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
American Airlines
7.1
Good
11,810 reviews
United Airlines
7.4
Good
9,983 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.7

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 20 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 $189, Southwest can have you in Greenville from Chicago in 3h 30m. There are 562 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 ($146), American Airlines ($202), and United Airlines ($212) 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 cheapest airlines to fly from Chicago to Greenville one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $118. American Airlines flights start at $133 while deals on United Airlines start at $133 one-way.

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

    Consider Republic Airways (100%), Avianca (85%) or United Airlines (82%) 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 $154. While the most popular route (Chicago O'Hare Intl - Greenville) can be booked for $251 on average, our data indicates $319 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, June is the cheapest month in which you can book a flight from Chicago to Greenville (average of $146). Flying from Chicago to Greenville in August is currently the most expensive (average of $209). 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
Greer
Simpsonville
Greenwood
Duncan
Seneca

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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 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 July 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$146Average$194FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$202Average$299FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$212Average$322FlexibilityNo cancel feeOn-time69%

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