Greenville

$125+ Cheap flights from Chicago (CHI) to Greenville (GSP)

CHI — GSP
Dec 11 — Dec 181
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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Chicago to Greenville are usually found in February or August, booked 78 days in advance, depart on a Saturday or Monday and return on a Thursday

Cheap flight deals from Chicago to Greenville

Cheapest flights from Chicago to Greenville

Sat 12/194:45 pm -
2 stops15h 47m
Wed 12/233:13 pm -
1 stop26h 46m
Deal found 11/8$323
Sun 12/1310:29 pm -
2 stops14h 39m
Sat 12/193:54 pm -
1 stop25h 58m
Deal found 11/7$327
Mon 12/1410:29 pm -
2 stops16h 00m
Sat 12/193:54 pm -
1 stop25h 58m
Deal found 11/7$328
Mon 12/76:07 am -
1 stop7h 01m
Thu 12/104:02 pm -
2 stops30h 27m
Deal found 11/8$333
Tue 11/176:30 am -
2 stops36h 37m
Fri 11/202:42 pm -
1 stop9h 52m
Deal found 11/10$338
Mon 11/167:55 am -
2 stops11h 17m
Thu 11/198:44 am -
1 stop7h 53m
Deal found 11/8$339
Wed 12/91:10 pm -
Nonstop2h 00m
Wed 12/1611:36 am -
Nonstop2h 24m
Deal found 11/9$345
Tue 11/176:30 am -
2 stops36h 37m
Sat 11/215:06 pm -
1 stop7h 28m
Deal found 11/7$346
Wed 11/186:30 am -
2 stops26h 02m
Fri 11/202:42 pm -
1 stop9h 52m
Deal found 11/10$348
Fri 12/45:55 pm -
Nonstop2h 04m
Sun 12/66:30 am -
Nonstop2h 16m
Deal found 11/8$349
Thu 12/33:36 pm -
1 stop23h 11m
Mon 12/72:42 pm -
2 stops21h 51m
Deal found 11/8$350
Fri 12/45:12 pm -
1 stop5h 35m
Mon 12/77:25 pm -
1 stop4h 29m
Deal found 11/10$369

Find flight deals from Chicago to Greenville

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(Kiwi.com)

One-way from

$125
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$384

Good round-trip deal

$339 or less

Good one-way deal

$264 or less
Provider with most accurate pricing for Chicago (CHI)-Greenville flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Greenville flights.
From Chicago (CHI) to Greenville
One-way flight from Chicago (CHI) to Greenville
Highest demand for flights based on searches. 3% potential increase in price ($10 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in November 2026
Price to beat on a round-trip flight from Chicago (CHI) to Greenville.
Price to beat on a one-way flight from Chicago (CHI) to Greenville.

Cheapflights Fare Finder

 
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 Chicago Midway - GSP Greenville

MDWGSP

Chicago Midway

Thu 12/17

4:00 pm-11:00 pm

1 stop6h 00m

Greenville

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$185

ChicagoGreenville

ORD Chicago O'Hare Intl - GSP Greenville

ORDGSP

Chicago O'Hare Intl

Tue 12/8

3:59 pm-10:22 pm

1 stop5h 23m

Greenville

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$185

ChicagoGreenville

MDW Chicago Midway - GSP Greenville

MDWGSP

Chicago Midway

Wed 12/16

12:45 pm-6:10 pm

1 stop4h 25m

Greenville

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$185

ChicagoGreenville

MDW Chicago Midway - GSP Greenville

MDWGSP

Chicago Midway

Tue 12/15

12:50 pm-7:55 pm

1 stop6h 05m

Greenville

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$185

ChicagoGreenville

MDW Chicago Midway - GSP Greenville

MDWGSP

Chicago Midway

Wed 12/16

5:12 pm-10:22 pm

1 stop4h 10m

Greenville

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$190
Quickest round-trip

ChicagoGreenville

ORD Chicago O'Hare Intl - GSP Greenville

ORDGSP

Chicago O'Hare Intl

Tue 12/1

1:34 pm-6:20 pm

1 stop3h 46m

Greenville

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$190

ChicagoGreenville

ORD Chicago O'Hare Intl - GSP Greenville

ORDGSP

Chicago O'Hare Intl

Sat 12/12

1:34 pm-7:57 pm

1 stop5h 23m

Greenville

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$190

ChicagoGreenville

ORD Chicago O'Hare Intl - GSP Greenville

ORDGSP

Chicago O'Hare Intl

Wed 12/16

5:02 pm-9:49 pm

1 stop3h 47m

Greenville

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$190

ChicagoGreenville

MDW Chicago Midway - GSP Greenville

MDWGSP

Chicago Midway

Tue 12/29

1:11 pm-1:43 pm

2 stops23h 32m

Greenville

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$200

ChicagoGreenville

ORD Chicago O'Hare Intl - GSP Greenville

ORDGSP

Chicago O'Hare Intl

Sat 1/2

8:59 am-7:53 am

1 stop21h 54m

Greenville

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$208

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 39 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Greenville

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Greenville in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 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

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, February is the cheapest month in which you can book a flight from Chicago to Greenville (average of $291). Flying from Chicago to Greenville in May is currently the most expensive (average of $370). 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?

It’s optimal to fly from Chicago to Greenville in the afternoon. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from Chicago to Greenville

The most flights from CHI to GSP are scheduled on a Monday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).

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

Airfare is typical for this route at the moment.
Chicago to Greenville flights typically cost between $319 and $498 in January.
The cheapest round-trip price found within the last 5 days was $319 on Multiple Airlines (Jan 7-Jan 11).

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

Booking 75 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?

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

Reviews of airlines servicing Greenville

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.

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.3

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.3

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.3

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible

Related info for your journey

  • 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 22 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 2 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 $359, American Airlines can have you in Greenville from Chicago in 5h 46m. 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, American Airlines ($209), and United Airlines ($218) offers the cheapest pricing from Chicago to Greenville. American Airlines is 38% 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 $133. United Airlines flights start at $133 while deals on Southwest start at $159 one-way.

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

    Consider Lufthansa (90%), American Airlines (87%) or Envoy Air (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 $159. While the most popular route (Chicago O'Hare Intl - Greenville) can be booked for $300 on average, our data indicates $373 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 $291). Flying from Chicago to Greenville in May is currently the most expensive (average of $370). 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
Anderson
Seneca

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Alternative routes for Chicago to Greenville

Top 2 airlines flying from Chicago to Greenville

AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$319FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$340FlexibilityNo cancel feeOn-time69%

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