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$95+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheapflights Tip: The best prices from Greenville to Chicago are usually found in November or April, booked 60 days in advance, depart on a Saturday or Thursday and return on a Saturday

Cheap 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 January 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/262:12 pm
GSP
-
ORD
1 stop6h 25m
Multiple Airlines
Thu 3/53:21 pm
ORD
-
GSP
1 stop25h 32m
Multiple Airlines
Deal found 1/27$201
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:29 am
GSP
-
ORD
Nonstop2h 16m
American Airlines
Sun 2/228:00 am
ORD
-
GSP
Nonstop1h 56m
American Airlines
Deal found 1/28$209
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Sat 3/217:40 am
GSP
-
ORD
Nonstop2h 16m
American Airlines
Mon 3/238:50 pm
ORD
-
GSP
Nonstop1h 52m
American Airlines
Deal found 1/26$211
This American Airlines deal was found by Cheapflights users on 1/27. 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 5/18:19 pm
GSP
-
ORD
Nonstop2h 20m
American Airlines
Wed 5/68:55 pm
ORD
-
GSP
Nonstop2h 03m
American Airlines
Deal found 1/27$212
This United Airlines deal was found by Cheapflights users on 1/27. 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 3/145:32 pm
GSP
-
ORD
Nonstop2h 28m
United Airlines
Tue 3/178:50 am
ORD
-
GSP
1 stop4h 27m
United Airlines
Deal found 1/27$219
This American Airlines deal was found by Cheapflights users on 1/27. 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 6/236:51 pm
GSP
-
ORD
Nonstop2h 24m
American Airlines
Mon 6/296:43 pm
ORD
-
GSP
Nonstop2h 08m
American Airlines
Deal found 1/27$224
This Delta deal was found by Cheapflights users on 1/26. 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 2/207:40 pm
GSP
-
ORD
1 stop5h 16m
Delta
Tue 2/249:35 am
ORD
-
GSP
1 stop6h 39m
Delta
Deal found 1/26$229
This Delta deal was found by Cheapflights users on 1/26. 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 4/238:50 am
GSP
-
MDW
1 stop4h 17m
Delta
Sun 4/266:00 am
MDW
-
GSP
1 stop5h 21m
Delta
Deal found 1/26$229
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/136:00 am
GSP
-
ORD
1 stop5h 12m
American Airlines
Mon 2/168:50 pm
ORD
-
GSP
Nonstop1h 52m
American Airlines
Deal found 1/26$239
This Delta deal was found by Cheapflights users on 1/26. 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 4/25:40 am
GSP
-
MDW
1 stop5h 16m
Delta
Mon 4/66:07 pm
MDW
-
GSP
1 stop4h 47m
Delta
Deal found 1/26$254
This Southwest deal was found by Cheapflights users on 1/27. 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.
Tue 3/1712:35 pm
GSP
-
MDW
1 stop5h 30m
Southwest
Mon 3/234:05 pm
MDW
-
GSP
1 stop5h 40m
Southwest
Deal found 1/27$260
This Southwest deal was found by Cheapflights users on 1/25. 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 3/71:55 pm
GSP
-
MDW
1 stop7h 15m
Southwest
Wed 3/1110:30 am
MDW
-
GSP
2 stops9h 00m
Southwest
Deal found 1/25$265

Find 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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$201
(Kiwi.com)

One-way from

$95
(Kiwi.com)

Popular in

January

Cheapest in

November

Average price

$339

Good round-trip deal

$361 or less

Good one-way deal

$228 or less
Provider with most accurate pricing for Greenville-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Greenville-Chicago (CHI) flights.
Search Deals
From Greenville to Chicago (CHI)
Search Deals
One-way flight from Greenville to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Greenville to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Greenville to Chicago (CHI).
Search Deals

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 January 28, 2026.
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

Sat 3/7

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

Wed 3/11

5:55 pm-8:51 pm

Nonstop1h 56m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 5/1

8:19 pm-9:39 pm

Nonstop2h 20m

Chicago O'Hare Intl

Mon 5/4

8:55 pm-11:58 pm

Nonstop2h 03m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 2/26

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

Sun 3/1

7:05 am-10:01 am

Nonstop1h 56m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 3/12

8:17 pm-9:36 pm

Nonstop2h 19m

Chicago O'Hare Intl

Mon 3/16

8:00 am-10:56 am

Nonstop1h 56m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 3/14

5:32 pm-7:00 pm

Nonstop2h 28m

Chicago O'Hare Intl

Tue 3/17

1:55 pm-4:51 pm

Nonstop1h 56m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 2/28

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

Tue 3/3

7:05 am-10:01 am

Nonstop1h 56m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Wed 4/1

6:30 am-7:54 am

Nonstop2h 24m

Chicago O'Hare Intl

Thu 4/9

7:00 am-9:56 am

Nonstop1h 56m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Wed 2/25

10:40 am-12:00 pm

Nonstop2h 20m

Chicago O'Hare Intl

Wed 3/4

7:05 am-10:01 am

Nonstop1h 56m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 2/19

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

Sun 2/22

7:05 am-10:01 am

Nonstop1h 56m

$209

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 2/24

10:00 am-2:20 pm

1 stop5h 20m

Chicago O'Hare Intl

Tue 3/3

7:05 am-10:01 am

Nonstop1h 56m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 38 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 FlightHub the most. FlightHub 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 January 23, 2026.

To ensure you get the cheapest price possible for a flight from Greenville to Chicago, you should look to book at least 60 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, January is the cheapest month in which you can book a flight from Greenville to Chicago (average of $58). Flying from Greenville to Chicago in April is currently the most expensive (average of $126). 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 January 28, 2026.

It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 64% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Greenville to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Greenville to Chicago. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Greenville to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 January 28, 2026.

The most flights from GSP to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).

How much does it cost to fly round-trip from Greenville to Chicago?

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 January 28, 2026.
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
4,267 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,124 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,212 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,201 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 15 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 3 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 $209, United Airlines can have you in Chicago from Greenville in 2h 20m. 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 ($107), American Airlines ($200), and United Airlines ($202) offers the cheapest pricing from Greenville to Chicago. You may be able to fly from Greenville to Chicago for 62% less than the average price by searching for these airlines.

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

    Consider PSA Airlines (100%), ANA (71%) or SkyWest Airlines (69%) 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 $1,260, our data shows the cheapest flight currently is $163. 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, January is the cheapest month in which you can book a flight from Greenville to Chicago (average of $58). Flying from Greenville to Chicago in April is currently the most expensive (average of $126). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Greenville to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Greenville to Chicago

Discover the top 3 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$107Average$279FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$200Average$293FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$202Average$323FlexibilityNo cancel feeOn-time69%

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