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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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Greenville to Chicago are usually found in April or November, booked 26 days in advance, depart on a Saturday or Thursday 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 junio 12, 2025.

Round-trip from

$209
(American Airlines)

One-way from

$108
(Delta)

Popular in

September

Cheapest in

April

Average price

$289

Good round-trip deal

$319 or less

Good one-way deal

$249 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 ($20 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 June 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 junio 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/10. 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.
vie. 11/712:37 pmGSP - ORD
Nonstop2h 14mUnited Airlines
lun. 11/105:50 pmORD - GSP
Nonstop1h 59mUnited Airlines
Deal found 6/10$209
This Southwest deal was found by Cheapflights users on 6/11. 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.
sáb. 8/95:05 pmGSP - MDW
1 stop4h 40mSouthwest
sáb. 8/239:35 amMDW - GSP
1 stop5h 55mSouthwest
Deal found 6/11$215
This Delta deal was found by Cheapflights users on 6/12. 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.
mié. 8/134:00 pmGSP - ORD
1 stop6h 36mDelta
mié. 8/2710:30 amORD - GSP
1 stop6h 48mDelta
Deal found 6/12$217
This Delta deal was found by Cheapflights users on 6/11. 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.
sáb. 7/127:00 amGSP - MDW
1 stop6h 29mDelta
mié. 7/166:00 amMDW - GSP
1 stop3h 59mDelta
Deal found 6/11$217
This American Airlines deal was found by Cheapflights users on 6/11. 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.
mar. 8/127:33 amGSP - ORD
Nonstop2h 22mAmerican Airlines
sáb. 8/167:08 pmORD - GSP
Nonstop1h 57mAmerican Airlines
Deal found 6/11$219
This Mytrip deal was found by Cheapflights users on 6/10. 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.
dom. 7/133:34 pmGSP - ORD
2 stops30h 56mMultiple Airlines
mié. 7/165:05 amORD - GSP
1 stop14h 47mMultiple Airlines
Deal found 6/10$257
This Southwest deal was found by Cheapflights users on 6/11. 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.
mié. 8/1310:25 amGSP - ORD
2 stops12h 05mSouthwest
mié. 8/271:50 pmORD - GSP
1 stop5h 05mSouthwest
Deal found 6/11$285
This Mytrip deal was found by Cheapflights users on 6/11. 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.
jue. 6/262:19 pmGSP - MDW
2 stops20h 25mMultiple Airlines
lun. 6/308:05 amMDW - GSP
3 stops25h 18mMultiple Airlines
Deal found 6/11$684

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 junio 12, 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

vie. 11/7

12:37 pm-1:51 pm

Nonstop2h 14m

Chicago O'Hare Intl

lun. 11/10

5:50 pm-8:49 pm

Nonstop1h 59m

$209

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

sáb. 8/9

5:05 pm-8:45 pm

1 stop4h 40m

Chicago Midway

sáb. 8/23

9:35 am-4:30 pm

1 stop5h 55m

$215

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

mié. 8/13

7:48 am-12:16 pm

1 stop5h 28m

Chicago O'Hare Intl

mié. 8/27

10:30 am-6:18 pm

1 stop6h 48m

$217

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

sáb. 7/12

7:00 am-12:29 pm

1 stop6h 29m

Chicago Midway

mié. 7/16

6:00 am-10:59 am

1 stop3h 59m

$217

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

mar. 8/12

7:33 am-8:55 am

Nonstop2h 22m

Chicago O'Hare Intl

sáb. 8/16

7:08 pm-10:05 pm

Nonstop1h 57m

$219

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

dom. 7/13

3:34 pm-9:30 pm

2 stops30h 56m

Chicago O'Hare Intl

mié. 7/16

5:05 am-8:52 pm

1 stop14h 47m

$257

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

mié. 8/13

10:25 am-9:30 pm

2 stops12h 05m

Chicago O'Hare Intl

mié. 8/27

1:50 pm-7:55 pm

1 stop5h 05m

$285

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

jue. 6/26

2:19 pm-9:44 am

2 stops20h 25m

Chicago Midway

lun. 6/30

8:05 am-10:23 am

3 stops25h 18m

$684

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

sáb. 7/5

7:00 am-10:03 am

1 stop4h 03m

$108

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

sáb. 7/5

7:00 am-12:29 pm

1 stop6h 29m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 16 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 9, 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 junio 12, 2025.

It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 67% on the flight price compared to flying in the afternoon, 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 junio 12, 2025.

The most flights from GSP to CHI are scheduled on a Wednesday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 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 junio 12, 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
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

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
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

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
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

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 18 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 Southwest ($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 Delta, with whom users have recently found tickets for as low as $108. However, be on the lookout for offers from Allegiant Air 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 Republic Airways (95%), ANA (87%) or GoJet (86%) 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 $1,530, our data shows the cheapest flight currently is $183. 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
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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$180Average$330FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$304FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$220Average$364FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$304Average$402FlexibilityNo cancel feeOn-time63%

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