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$108+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
mai 6 — mai 131
mar. 5/6
mar. 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Greenville to Chicago are usually found in April or February, booked 26 days in advance, depart on a Friday or Saturday and return on a Tuesday

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 mai 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$218
(United Airlines)

One-way from

$108
(Delta)

Popular in

September

Cheapest in

April

Average price

$328

Good round-trip deal

$280 or less

Good one-way deal

$209 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. 2% potential increase in price ($9 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 May 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 mai 1, 2025.

This United Airlines deal was found by Cheapflights users on 4/29. 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.
ven. 7/252:52 pmGSP - ORD
1 stop7h 24mUnited Airlines
sam. 7/261:55 pmORD - GSP
Nonstop1h 59mUnited Airlines
Deal found 4/29$218
This Delta deal was found by Cheapflights users on 4/29. 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.
jeu. 6/127:00 amGSP - ORD
1 stop6h 55mDelta
sam. 6/141:35 pmORD - GSP
1 stop4h 06mDelta
Deal found 4/29$222
This Delta deal was found by Cheapflights users on 4/28. 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.
ven. 7/251:59 pmGSP - MDW
1 stop5h 03mDelta
sam. 7/2612:38 pmMDW - GSP
1 stop5h 06mDelta
Deal found 4/28$222
This American Airlines deal was found by Cheapflights users on 4/30. 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.
jeu. 6/196:41 pmGSP - ORD
Nonstop2h 08mAmerican Airlines
sam. 6/218:13 amORD - GSP
Nonstop1h 50mAmerican Airlines
Deal found 4/30$233
This Southwest deal was found by Cheapflights users on 4/30. 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.
ven. 8/227:40 amGSP - MDW
2 stops6h 30mSouthwest
mar. 8/2611:45 amMDW - GSP
1 stop7h 10mSouthwest
Deal found 4/30$244
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/169:23 pmGSP - ORD
2 stops24h 00mMultiple Airlines
jeu. 6/267:56 amORD - GSP
1 stop12h 28mMultiple Airlines
Deal found 4/29$272
This Southwest deal was found by Cheapflights users on 4/29. 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.
mar. 5/68:10 amGSP - ORD
1 stop4h 40mSouthwest
mar. 5/61:50 pmORD - GSP
1 stop5h 20mSouthwest
Deal found 4/29$295

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 mai 1, 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

ven. 7/25

2:52 pm-9:16 pm

1 stop7h 24m

Chicago O'Hare Intl

sam. 7/26

1:55 pm-4:54 pm

Nonstop1h 59m

$218

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

jeu. 6/12

5:30 am-8:39 am

1 stop4h 09m

Chicago O'Hare Intl

sam. 6/14

11:20 am-6:41 pm

1 stop6h 21m

$222

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

ven. 7/25

1:59 pm-6:02 pm

1 stop5h 03m

Chicago Midway

sam. 7/26

12:38 pm-6:44 pm

1 stop5h 06m

$222

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

jeu. 6/19

6:41 pm-7:49 pm

Nonstop2h 08m

Chicago O'Hare Intl

sam. 6/21

8:13 am-11:03 am

Nonstop1h 50m

$233

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

ven. 8/22

7:40 am-1:10 pm

2 stops6h 30m

Chicago Midway

mar. 8/26

11:45 am-7:55 pm

1 stop7h 10m

$244

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

lun. 6/16

9:23 pm-8:23 pm

2 stops24h 00m

Chicago O'Hare Intl

jeu. 6/26

7:56 am-9:24 pm

1 stop12h 28m

$272

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

mar. 6/17

7:20 am-11:50 am

1 stop5h 30m

Chicago O'Hare Intl

ven. 6/20

1:50 pm-10:00 pm

1 stop7h 10m

$296

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

dim. 5/25

5:30 am-8:29 am

1 stop3h 59m

$108

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

ven. 7/25

8:10 pm-1:05 am

1 stop5h 55m

$115

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

sam. 5/17

7:05 am-12:45 pm

1 stop6h 40m

$125

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 14 results
1
2

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice 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 Greenville-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Greenville-Chicago flight deals on Cheapflights vs. FlightHub >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 April 25, 2025.

To ensure you get the cheapest price possible for a flight from Greenville to Chicago, you should look to book at least 26 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, August is the cheapest month in which you can book a flight from Greenville to Chicago (average of $245). Flying from Greenville to Chicago in March is currently the most expensive (average of $321). 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 mai 1, 2025.

It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 68% on the flight price compared to flying in the morning, which is usually more expensive.

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 mai 1, 2025.

The most flights from GSP to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 mai 1, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Greenville to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 8 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 4 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.

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

    According to our current data, United Airlines ($218), Delta ($222), and American Airlines ($233) offers the cheapest pricing from Greenville to Chicago. You may be able to fly from Greenville to Chicago for 29% less than the average price by searching for these airlines.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $108. However, be on the lookout for offers from Southwest and American Airlines, as they are both options that can get you from Greenville to Chicago for a low price.

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

    Consider Avianca (86%), SkyWest Airlines (86%) or Qatar Airways (84%) 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 $1,298, our data shows the cheapest flight currently is $99. 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, August is the cheapest month in which you can book a flight from Greenville to Chicago (average of $245). Flying from Greenville to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 4 airlines flying from Greenville to Chicago

Discover the top 4 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 mai 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$180Average$327FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$311FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$363FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$304Average$397FlexibilityNo cancel feeOn-time63%

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