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$89+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Greenville to Chicago are usually found in November or April, booked 63 days in advance, depart on a Saturday or Friday 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 September 16, 2025.

Round-trip from

$206
(Delta)

One-way from

$89
(United Airlines)

Popular in

December

Cheapest in

November

Average price

$319

Good round-trip deal

$293 or less

Good one-way deal

$263 or less
From Greenville to Chicago (CHI)
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One-way flight from Greenville to Chicago (CHI)
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High demand for flights, 2% potential price rise
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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 September 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 September 16, 2025.

This Delta deal was found by Cheapflights users on 9/14. 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 10/1811:29 amGSP - ORD
1 stop5h 42mDelta
Wed 10/226:00 amORD - GSP
1 stop7h 30mDelta
Deal found 9/14$206
This Southwest deal was found by Cheapflights users on 9/14. 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.
Wed 10/296:05 amGSP - MDW
1 stop6h 55mSouthwest
Sat 11/111:45 amMDW - GSP
1 stop5h 30mSouthwest
Deal found 9/14$206
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/247:20 amGSP - ORD
Nonstop2h 28mAmerican Airlines
Sun 10/268:00 amORD - GSP
Nonstop1h 52mAmerican Airlines
Deal found 9/15$209
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/82:46 pmGSP - ORD
1 stop6h 12mUnited Airlines
Thu 10/98:50 amORD - GSP
1 stop4h 21mUnited Airlines
Deal found 9/15$210
This Delta deal was found by Cheapflights users on 9/15. 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 12/57:36 pmGSP - ORD
1 stop5h 25mDelta
Tue 12/165:03 pmORD - GSP
1 stop3h 38mDelta
Deal found 9/15$213
This Delta deal was found by Cheapflights users on 9/15. 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 12/57:27 amGSP - MDW
1 stop6h 07mDelta
Tue 12/96:00 amMDW - GSP
1 stop4h 16mDelta
Deal found 9/15$213
This Delta deal was found by Cheapflights users on 9/15. 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 10/257:05 amGSP - ORD
1 stop4h 15mDelta
Sat 11/86:10 pmORD - GSP
1 stop4h 45mDelta
Deal found 9/15$215
This Southwest deal was found by Cheapflights users on 9/15. 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 10/253:35 pmGSP - MDW
1 stop7h 50mSouthwest
Sat 11/85:50 amMDW - GSP
1 stop6h 10mSouthwest
Deal found 9/15$215
This Southwest deal was found by Cheapflights users on 9/14. 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 12/54:45 pmGSP - MDW
1 stop5h 20mSouthwest
Tue 12/96:40 amMDW - GSP
2 stops8h 25mSouthwest
Deal found 9/14$218
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/27:34 amGSP - ORD
Nonstop2h 24mAmerican Airlines
Sun 10/58:01 amORD - GSP
Nonstop1h 55mAmerican Airlines
Deal found 9/14$219
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 10/148:04 pmGSP - ORD
Nonstop2h 15mAmerican Airlines
Tue 10/218:35 amORD - GSP
1 stop4h 05mAmerican Airlines
Deal found 9/16$220
This Delta deal was found by Cheapflights users on 9/16. 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 10/247:41 pmGSP - ORD
1 stop5h 17mDelta
Mon 10/275:20 amORD - GSP
1 stop6h 30mDelta
Deal found 9/16$222

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 September 16, 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

Wed 10/8

2:46 pm-7:58 pm

1 stop6h 12m

Chicago O'Hare Intl

Thu 10/9

8:50 am-2:11 pm

1 stop4h 21m

$210

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 10/29

3:00 pm-10:25 pm

2 stops8h 25m

Chicago Midway

Sat 11/1

11:45 am-6:15 pm

1 stop5h 30m

$211

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 12/5

7:36 pm-12:01 am

1 stop5h 25m

Chicago O'Hare Intl

Tue 12/9

12:38 pm-10:04 pm

1 stop8h 26m

$213

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/12

4:15 pm-12:10 am

1 stop8h 55m

Chicago Midway

Tue 12/16

12:55 pm-7:50 pm

1 stop5h 55m

$213

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/5

7:27 am-12:34 pm

1 stop6h 07m

Chicago Midway

Tue 12/9

6:00 am-11:16 am

1 stop4h 16m

$213

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 12/5

4:45 pm-9:05 pm

1 stop5h 20m

Chicago Midway

Tue 12/9

8:50 am-4:05 pm

1 stop6h 15m

$213

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 10/25

9:45 am-2:58 pm

1 stop6h 13m

Chicago O'Hare Intl

Mon 10/27

6:45 am-12:50 pm

1 stop5h 05m

$215

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 11/8

7:30 am-12:40 pm

1 stop6h 10m

Chicago O'Hare Intl

Mon 11/10

5:50 pm-10:34 pm

1 stop3h 44m

$215

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 10/25

5:16 pm-10:14 pm

1 stop5h 58m

Chicago Midway

Mon 10/27

6:00 am-12:50 pm

1 stop5h 50m

$215

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 10/17

3:55 pm-5:05 pm

Nonstop2h 10m

Chicago O'Hare Intl

Sat 10/18

1:50 pm-4:53 pm

Nonstop2h 03m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 36 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 September 12, 2025.

To ensure you get the cheapest price possible for a flight from Greenville to Chicago, you should look to book at least 28 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 September 16, 2025.

It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 41% 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 September 16, 2025.

The most flights from GSP to CHI are scheduled on a Monday (21 on average). You will have fewer flight options on Saturday, 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 September 16, 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
4,242 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

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
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

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
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

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 17 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.

  • How long is the flight from Greenville to Chicago?

    For as low as $213, 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 ($202), and United Airlines ($212) offers the cheapest pricing from Greenville to Chicago. You may be able to fly from Greenville to Chicago for 37% 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 United Airlines, with whom users have recently found tickets for as low as $98. However, be on the lookout for offers from Delta and Southwest, 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 Emirates (100%), GoJet (99%) or Avianca (93%) 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 $883, our data shows the cheapest flight currently is $154. 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 Chicago?

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

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See prices for flight routes from nearby airports that may be better suited for you.
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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$180Average$271FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$202Average$298FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$212Average$352FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$232Average$402FlexibilityNo cancel feeOn-time63%

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