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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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Aug 21 — Aug 281
Thu 8/21
Thu 8/28
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 Wednesday

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 August 16, 2025.

Round-trip from

$209
(American Airlines)

One-way from

$99
(Delta)

Popular in

September

Cheapest in

November

Average price

$318

Good round-trip deal

$302 or less

Good one-way deal

$223 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. 8% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 16, 2025.

This American Airlines deal was found by Cheapflights users on 8/14. 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 9/47:36 amGSP - ORD
Nonstop2h 24mAmerican Airlines
Thu 9/118:01 amORD - GSP
Nonstop1h 55mAmerican Airlines
Deal found 8/14$209
This United Airlines deal was found by Cheapflights users on 8/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/259:35 amGSP - ORD
Nonstop2h 16mUnited Airlines
Sat 11/11:00 pmORD - GSP
1 stop5h 10mUnited Airlines
Deal found 8/14$211
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Sat 9/279:35 amGSP - ORD
Nonstop2h 16mUnited Airlines
Tue 9/308:50 amORD - GSP
1 stop4h 21mUnited Airlines
Deal found 8/15$212
This Delta deal was found by Cheapflights users on 8/14. 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.
Thu 9/47:05 amGSP - ORD
1 stop6h 40mDelta
Mon 9/82:00 pmORD - GSP
1 stop4h 23mDelta
Deal found 8/14$215
This Delta deal was found by Cheapflights users on 8/15. 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.
Tue 9/236:13 pmGSP - MDW
1 stop4h 23mDelta
Sat 9/2711:00 amMDW - GSP
1 stop4h 16mDelta
Deal found 8/15$215
This Delta deal was found by Cheapflights users on 8/15. 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 9/2011:24 amGSP - ORD
1 stop5h 56mDelta
Mon 9/227:00 amORD - GSP
1 stop6h 41mDelta
Deal found 8/15$216
This Delta deal was found by Cheapflights users on 8/15. 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 9/205:21 pmGSP - MDW
1 stop4h 49mDelta
Mon 9/226:30 pmMDW - GSP
1 stop4h 22mDelta
Deal found 8/15$216
This Delta deal was found by Cheapflights users on 8/14. 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.
Wed 9/177:05 amGSP - MDW
1 stop6h 23mDelta
Tue 9/236:00 amMDW - GSP
1 stop4h 24mDelta
Deal found 8/14$218
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Sat 9/69:17 amGSP - ORD
Nonstop2h 16mUnited Airlines
Mon 9/811:40 amORD - GSP
1 stop6h 12mUnited Airlines
Deal found 8/15$219
This Delta deal was found by Cheapflights users on 8/14. 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.
Tue 9/165:30 amGSP - ORD
1 stop4h 10mDelta
Thu 9/255:30 amORD - GSP
1 stop4h 54mDelta
Deal found 8/14$223
This Delta deal was found by Cheapflights users on 8/14. 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.
Thu 9/185:30 amGSP - MDW
1 stop5h 10mDelta
Tue 9/231:08 pmMDW - GSP
1 stop4h 06mDelta
Deal found 8/14$223
This Delta deal was found by Cheapflights users on 8/14. 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.
Sun 9/215:30 amGSP - ORD
1 stop4h 10mDelta
Tue 9/2311:20 amORD - GSP
1 stop4h 58mDelta
Deal found 8/14$224

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 August 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

Fri 10/17

8:04 pm-9:19 pm

Nonstop2h 15m

Chicago O'Hare Intl

Sun 10/19

7:00 pm-9:57 pm

Nonstop1h 57m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 9/6

9:17 am-10:33 am

Nonstop2h 16m

Chicago O'Hare Intl

Mon 9/8

7:35 pm-10:46 pm

Nonstop2h 11m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 11/20

8:14 pm-9:30 pm

Nonstop2h 16m

Chicago O'Hare Intl

Sun 11/23

8:05 am-10:58 am

Nonstop1h 53m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 11/6

8:14 pm-9:30 pm

Nonstop2h 16m

Chicago O'Hare Intl

Sun 11/9

6:53 pm-10:00 pm

Nonstop2h 07m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 10/30

7:20 am-8:48 am

Nonstop2h 28m

Chicago O'Hare Intl

Sun 11/2

6:53 pm-10:00 pm

Nonstop2h 07m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Wed 9/3

1:36 pm-2:49 pm

Nonstop2h 13m

Chicago O'Hare Intl

Sat 9/6

10:05 am-1:06 pm

Nonstop2h 01m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 11/13

11:28 am-12:39 pm

Nonstop2h 11m

Chicago O'Hare Intl

Sun 11/16

6:53 pm-10:00 pm

Nonstop2h 07m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 9/4

7:36 am-9:00 am

Nonstop2h 24m

Chicago O'Hare Intl

Thu 9/11

8:01 am-10:56 am

Nonstop1h 55m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 11/7

6:12 am-7:30 am

Nonstop2h 18m

Chicago O'Hare Intl

Sun 11/9

8:05 am-10:58 am

Nonstop1h 53m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 9/4

7:36 am-9:00 am

Nonstop2h 24m

Chicago O'Hare Intl

Mon 9/8

6:55 pm-9:54 pm

Nonstop1h 59m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 39 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 August 8, 2025.

To ensure you get the cheapest price possible for a flight from Greenville to Chicago, you should look to book at least 63 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 August 16, 2025.

It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 45% on the flight price compared to flying in the morning, which is usually more expensive.

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 August 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
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,985 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 11 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, Delta ($180), American Airlines ($202), and United Airlines ($209) offers the cheapest pricing from Greenville to Chicago. You may be able to fly from Greenville to Chicago for 39% less than the average price by searching for these airlines.

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

    Consider Avianca (89%), ANA (87%) or Republic 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 $532, our data shows the cheapest flight currently is $146. 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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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 August 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$180Average$279FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$202Average$296FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$355FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$304Average$402FlexibilityNo cancel feeOn-time63%

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