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$99+ Cheap flights from Greenville (GSP) to Chicago (CHI)

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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Dec 25 — Jan 11
Thu 12/25
Thu 1/1
1 adult, Economy
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Cheapflights Tip: The best prices from Greenville to Chicago are usually found in November or April, booked 57 days in advance, depart on a Thursday or Saturday and return on a Saturday

Cheap flight deals from Greenville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Greenville (GSP) to Chicago (CHI). 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 November 25, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$213
(Southwest)

One-way from

$99
(Southwest)

Popular in

December

Cheapest in

November

Average price

$265

Good round-trip deal

$294 or less

Good one-way deal

$253 or less
Provider with most accurate pricing for Greenville-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Greenville-Chicago (CHI) flights.
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From Greenville to Chicago (CHI)
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One-way flight from Greenville to Chicago (CHI)
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Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Greenville to Chicago (CHI).
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Price to beat on a one-way flight from Greenville to Chicago (CHI).
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Find flight deals from Greenville to Chicago

Cheapest flights from Greenville to Chicago
Explore the most affordable flight options available from Greenville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 25, 2025.

This American Airlines deal was found by Cheapflights users on 11/24. 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.
Thu 11/2711:28 amGSP - ORD
Nonstop2h 11mAmerican Airlines
Sat 11/297:12 pmORD - GSP
Nonstop2h 02mAmerican Airlines
Deal found 11/24$234
This American Airlines deal was found by Cheapflights users on 11/24. 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 12/126:21 pmGSP - ORD
1 stop5h 33mAmerican Airlines
Mon 12/158:05 amORD - GSP
Nonstop1h 56mAmerican Airlines
Deal found 11/24$239
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Fri 12/128:03 pmGSP - ORD
1 stop19h 18mMultiple Airlines
Mon 12/157:20 amORD - GSP
1 stop11h 03mMultiple Airlines
Deal found 11/24$240
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/153:00 pmGSP - ORD
1 stop21h 08mMultiple Airlines
Thu 12/185:00 amORD - GSP
1 stop27h 51mMultiple Airlines
Deal found 11/24$248
This United Airlines deal was found by Cheapflights users on 11/25. 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.
Wed 12/109:19 amGSP - ORD
Nonstop2h 14mUnited Airlines
Sun 12/148:45 amORD - GSP
Nonstop1h 59mUnited Airlines
Deal found 11/25$249
This Delta deal was found by Cheapflights users on 11/24. 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 12/125:35 amGSP - MDW
1 stop5h 19mDelta
Mon 12/155:29 pmMDW - GSP
1 stop5h 11mDelta
Deal found 11/24$249
This American Airlines deal was found by Cheapflights users on 11/23. 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 12/126:21 pmGSP - ORD
1 stop5h 33mAmerican Airlines
Sun 12/144:48 pmORD - GSP
Nonstop1h 56mAmerican Airlines
Deal found 11/23$254
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Fri 12/53:00 pmGSP - ORD
1 stop21h 08mMultiple Airlines
Sun 12/73:20 pmORD - GSP
1 stop21h 50mMultiple Airlines
Deal found 11/24$258
This American Airlines deal was found by Cheapflights users on 11/25. 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.
Sat 12/66:00 amGSP - ORD
Nonstop2h 13mAmerican Airlines
Wed 12/106:36 pmORD - GSP
Nonstop2h 09mAmerican Airlines
Deal found 11/25$261
This American Airlines deal was found by Cheapflights users on 11/25. 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 12/198:07 pmGSP - ORD
Nonstop2h 18mAmerican Airlines
Wed 12/241:27 pmORD - GSP
1 stop4h 16mAmerican Airlines
Deal found 11/25$264
This American Airlines deal was found by Cheapflights users on 11/24. 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 12/158:14 pmGSP - ORD
Nonstop2h 16mAmerican Airlines
Thu 12/188:05 amORD - GSP
Nonstop1h 56mAmerican Airlines
Deal found 11/24$267
This Delta deal was found by Cheapflights users on 11/23. 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 12/97:25 amGSP - MDW
1 stop6h 09mDelta
Sat 12/134:29 pmMDW - GSP
1 stop6h 12mDelta
Deal found 11/23$269

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated November 25, 2025.
Use the filters below to find and compare flights from Greenville to Chicago that are best for you.

Fly from

Greenville

Fly to

Chicago

Route

Depart

Return

Price

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 1/31

10:00 am-2:25 pm

1 stop5h 25m

Chicago O'Hare Intl

Sun 2/1

7:10 am-10:16 am

Nonstop2h 06m

$212

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Wed 4/8

6:00 am-11:15 am

1 stop6h 15m

Chicago O'Hare Intl

Sat 4/11

5:29 pm-10:42 pm

1 stop4h 13m

$215

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 1/24

7:10 am-12:25 pm

1 stop6h 15m

Chicago O'Hare Intl

Sat 1/31

5:30 am-11:08 am

1 stop4h 38m

$215

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Wed 4/1

6:00 am-11:15 am

1 stop6h 15m

Chicago O'Hare Intl

Sat 4/4

5:29 pm-10:42 pm

1 stop4h 13m

$215

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 2/20

6:49 am-10:08 am

1 stop4h 19m

Chicago O'Hare Intl

Tue 2/24

6:45 am-2:02 pm

1 stop6h 17m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 2/20

7:40 pm-10:42 pm

1 stop4h 02m

Chicago Midway

Tue 2/24

6:00 am-11:08 am

1 stop4h 08m

$215

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 1/30

10:00 am-2:25 pm

1 stop5h 25m

Chicago O'Hare Intl

Sun 2/1

1:55 pm-4:52 pm

Nonstop1h 57m

$219

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 2/19

6:00 am-1:23 pm

1 stop8h 23m

Chicago O'Hare Intl

Mon 2/23

2:30 pm-10:13 pm

1 stop6h 43m

$222

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 1/10

7:20 am-1:08 pm

1 stop6h 48m

Chicago O'Hare Intl

Sun 1/11

5:30 am-11:08 am

1 stop4h 38m

$222

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 2/3

5:40 am-10:05 am

1 stop5h 25m

Chicago O'Hare Intl

Fri 3/6

2:46 pm-8:19 pm

1 stop4h 33m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 41 results
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Compare providers for flights from Greenville to Chicago

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 Greenville to Chicago in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 Greenville-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Greenville-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Greenville-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Greenville-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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 Greenville-Chicago 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 Greenville to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Greenville 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 Greenville to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from Greenville to Chicago. Price data was last updated on November 21, 2025.

To ensure you get the cheapest price possible for a flight from Greenville to Chicago, you should look to book at least 57 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, February is the cheapest month in which you can book a flight from Greenville to Chicago (average of $57). Flying from Greenville to Chicago in June is currently the most expensive (average of $161). 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 GSP to CHI?

Find hourly flight availability from Greenville to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 25, 2025.

It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 27% on the flight price compared to flying at noon, which is usually more expensive.

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

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

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

Weekly flight availability from Greenville to Chicago

Explore weekly flight availability from Greenville to Chicago. 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 November 25, 2025.

The most flights from GSP to CHI are scheduled on a Tuesday (20 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (3 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 25, 2025.
Read through reviews of airlines operating flights from Greenville to Chicago, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,999 reviews
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,046 reviews
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,038 reviews
Southwest
8.0
Very good
4,254 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Greenville to Chicago. 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 from for flights from Greenville to Chicago?

    Greenville (GSP) is the airport you will fly out of if you book a flight from Greenville to Chicago. You should not have trouble finding flights to Chicago from Greenville; the airport handles an average of 14 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 3 airlines have flights from the Greenville airport to Chicago. It is only a 10.4 mi journey to Greenville (GSP) from Greenville’s city center.

  • How long is the flight from Greenville to Chicago?

    For as low as $212, United Airlines can have you in Chicago from Greenville in 5h 25m. Greenville and Chicago are separated by a distance of 577 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    According to our current data, Delta ($180), American Airlines ($201), and United Airlines ($209) offers the cheapest pricing from Greenville to Chicago. You may be able to fly from Greenville to Chicago for 38% less than the average price by searching for these airlines.

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

    Consider Qatar Airways (97%), Republic Airways (96%) or PSA Airlines (95%) when booking your flight. These represent the most reliable airlines when flying from Greenville to Chicago.

  • What are the cheapest flights from Greenville to Chicago?

    While on average a flight from Greenville to Chicago is generally $1,024, our data shows the cheapest flight currently is $133. When looking at the most popular route, (Greenville - Chicago O'Hare Intl), you can expect to pay $195 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Greenville to Chicago 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 Greenville to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Greenville to Chicago (average of $57). Flying from Greenville to Chicago in June is currently the most expensive (average of $161). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Top 3 airlines flying from Greenville to Chicago

Discover the top 3 airlines that operate flights from Greenville to Chicago. 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 November 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$180Average$271FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$201Average$296FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$206Average$338FlexibilityNo cancel feeOn-time69%

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