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$103+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
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Cheapflights Tip: The best prices from Greenville to Chicago are usually found in November or April, booked 26 days in advance, depart on a Thursday 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 July 1, 2025.

Round-trip from

$209
(American Airlines)

One-way from

$103
(Mytrip)

Popular in

September

Cheapest in

November

Average price

$289

Good round-trip deal

$307 or less

Good one-way deal

$268 or less
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. 6% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 1, 2025.

This American Airlines deal was found by Cheapflights users on 6/30. 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.
Fri 8/157:46 pmGSP - ORD
Nonstop2h 11mAmerican Airlines
Mon 8/187:08 pmORD - GSP
Nonstop1h 57mAmerican Airlines
Deal found 6/30$209
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/249:35 amGSP - ORD
Nonstop2h 16mUnited Airlines
Wed 10/298:50 amORD - GSP
1 stop4h 20mUnited Airlines
Deal found 6/30$212
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/27:00 amGSP - ORD
1 stop4h 16mDelta
Tue 8/59:25 amORD - GSP
1 stop8h 05mDelta
Deal found 6/30$215
This Delta deal was found by Cheapflights users on 7/1. 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 8/165:20 pmGSP - MDW
1 stop4h 52mDelta
Tue 8/196:04 amMDW - GSP
1 stop4h 25mDelta
Deal found 7/1$215
This Southwest deal was found by Cheapflights users on 6/30. 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.
Sat 9/65:05 pmGSP - MDW
1 stop4h 40mSouthwest
Sun 9/710:15 amMDW - GSP
2 stops8h 00mSouthwest
Deal found 6/30$263
This Southwest deal was found by Cheapflights users on 7/1. 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 9/2610:45 amGSP - ORD
1 stop6h 40mSouthwest
Sun 9/281:50 pmORD - GSP
1 stop7h 15mSouthwest
Deal found 7/1$275
This Mytrip deal was found by Cheapflights users on 6/29. 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.
Fri 7/184:05 pmGSP - ORD
1 stop8h 48mMultiple Airlines
Mon 7/215:05 amORD - GSP
1 stop9h 10mMultiple Airlines
Deal found 6/29$283

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 July 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

Fri 8/15

7:46 pm-8:57 pm

Nonstop2h 11m

Chicago O'Hare Intl

Mon 8/18

7:08 pm-10:05 pm

Nonstop1h 57m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 8/2

7:45 pm-11:30 pm

1 stop4h 45m

Chicago O'Hare Intl

Tue 8/5

8:55 am-12:04 pm

Nonstop2h 09m

$212

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 8/2

7:00 am-10:16 am

1 stop4h 16m

Chicago O'Hare Intl

Tue 8/5

9:25 am-6:30 pm

1 stop8h 05m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 8/16

5:20 pm-9:12 pm

1 stop4h 52m

Chicago Midway

Tue 8/19

6:04 am-11:29 am

1 stop4h 25m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 9/6

5:05 pm-8:45 pm

1 stop4h 40m

Chicago Midway

Sun 9/7

10:15 am-7:15 pm

2 stops8h 00m

$263

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 9/26

10:45 am-4:25 pm

1 stop6h 40m

Chicago O'Hare Intl

Sun 9/28

1:50 pm-10:05 pm

1 stop7h 15m

$275

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 8/8

4:05 pm-11:58 pm

1 stop8h 53m

Chicago O'Hare Intl

Mon 8/11

5:05 am-3:15 pm

1 stop9h 10m

$280

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Mon 8/11

4:05 pm-11:58 pm

1 stop8h 53m

$103

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Mon 8/4

8:07 pm-12:09 am

1 stop5h 02m

$115

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Tue 8/26

6:30 am-9:36 am

1 stop4h 06m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

Showing 1-10 of 14 results
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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 June 27, 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 July 1, 2025.

It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 66% 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 July 1, 2025.

The most flights from GSP to CHI are scheduled on a Monday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 July 1, 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
4,273 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,858 reviews
Southwest
8.0
Very good
4,273 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,273 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.2
Good
710 reviews
Southwest
8.0
Very good
4,273 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 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, American Airlines ($209), United Airlines ($212), and Delta ($215) offers the cheapest pricing from Greenville to Chicago. You may be able to fly from Greenville to Chicago for 30% 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 Southwest, with whom users have recently found tickets for as low as $108. However, be on the lookout for offers from Delta and Allegiant Air, 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 Republic Airways (96%), ANA (89%) or United Airlines (85%) 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 $1,263, our data shows the cheapest flight currently is $180. When looking at the most popular route, (Greenville - Chicago O'Hare Intl), you can expect to pay $209 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
Lansing
Benton Harbor
Porter
Hammond
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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$180Average$330FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$300FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$213Average$365FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$304Average$402FlexibilityNo cancel feeOn-time63%

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