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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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Feb 26 — Mar 51
Wed 2/26
Wed 3/5
1 adult, Economy
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The best prices from Greenville to Chicago are usually found in January or November, booked 48 days in advance, depart on a Friday 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 February 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$242
(Mytrip)

One-way from

$89
(Mytrip)

Popular in

June

Cheapest in

January

Average price

$334

Good round-trip deal

$354 or less

Good one-way deal

$174 or less
Provider with most accurate pricing for Greenville-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Greenville-Chicago (CHI) flights.
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From Greenville to Chicago (CHI)
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One-way flight from Greenville to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 21, 2025.

This Mytrip deal was found by Cheapflights users on 2/20. 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.
Thu 3/2010:03 amGSP - ORD
1 stop11h 39mMultiple Airlines
Thu 3/274:40 pmORD - GSP
1 stop27h 40mMultiple Airlines
Deal found 2/20$242
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/47:45 amGSP - ORD
Nonstop2h 05mAmerican Airlines
Sat 3/87:03 pmORD - GSP
Nonstop1h 51mAmerican Airlines
Deal found 2/20$243
This United Airlines deal was found by Cheapflights users on 2/20. 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 7/307:49 pmGSP - ORD
1 stop4h 27mUnited Airlines
Sun 8/38:45 amORD - GSP
Nonstop2h 09mUnited Airlines
Deal found 2/20$244
This Delta deal was found by Cheapflights users on 2/20. 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 3/217:00 amGSP - ORD
1 stop4h 10mDelta
Sat 3/2911:13 amORD - GSP
1 stop5h 20mDelta
Deal found 2/20$247
This Delta deal was found by Cheapflights users on 2/20. 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 3/157:30 amGSP - MDW
1 stop6h 02mDelta
Mon 3/172:55 pmMDW - GSP
1 stop6h 00mDelta
Deal found 2/20$251
This Southwest deal was found by Cheapflights users on 2/20. 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 3/2112:00 pmGSP - ORD
2 stops10h 30mSouthwest
Sat 3/294:00 pmORD - GSP
1 stop5h 20mSouthwest
Deal found 2/20$276
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 3/2712:00 pmGSP - MDW
1 stop3h 55mSouthwest
Sun 3/307:20 amMDW - GSP
1 stop3h 35mSouthwest
Deal found 2/20$326

Find flights from Greenville to Chicago within your budget

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 February 21, 2025.

Fly from

Greenville

Fly to

Chicago

Route

Depart

Return

Price

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 3/20

10:03 am-8:42 pm

1 stop11h 39m

Chicago O'Hare Intl

Thu 3/27

4:40 pm-9:20 pm

1 stop27h 40m

$242

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 3/4

7:45 am-8:50 am

Nonstop2h 05m

Chicago O'Hare Intl

Wed 3/12

7:00 pm-9:51 pm

Nonstop1h 51m

$243

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Wed 7/30

7:49 pm-11:16 pm

1 stop4h 27m

Chicago O'Hare Intl

Sun 8/3

8:45 am-11:54 am

Nonstop2h 09m

$244

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 3/21

7:00 am-10:10 am

1 stop4h 10m

Chicago O'Hare Intl

Sat 3/29

11:13 am-5:33 pm

1 stop5h 20m

$247

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 3/15

7:30 am-12:32 pm

1 stop6h 02m

Chicago Midway

Mon 3/17

2:55 pm-9:55 pm

1 stop6h 00m

$251

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 3/21

12:00 pm-9:30 pm

2 stops10h 30m

Chicago O'Hare Intl

Sat 3/29

4:00 pm-10:20 pm

1 stop5h 20m

$276

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Thu 3/27

12:00 pm-2:55 pm

1 stop3h 55m

Chicago Midway

Sun 3/30

7:20 am-11:55 am

1 stop3h 35m

$326

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 3/7

4:35 pm-9:39 am

1 stop18h 04m

$89

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Thu 3/20

8:00 am-9:10 am

Nonstop2h 10m

$110

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 3/18

5:47 am-10:06 am

1 stop5h 19m

$120

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 14 results
1
2

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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.

Travel insights for flights from Greenville to Chicago

Get recent, data-driven insights about flights from Greenville to Chicago including ideal travel times, pricing trends, and more.

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 February 14, 2025.

To ensure you get the cheapest price possible for a flight from Greenville to Chicago, you should look to book at least 48 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 February 21, 2025.

It’s typically best to fly out from Greenville to Chicago in the evening. Doing so could potentially save you 69% on the flight price compared to flying in the morning, 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 December 16, 2024.

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 afternoons 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 February 21, 2025.

The most flights from GSP to CHI are scheduled on a Thursday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 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 February 21, 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
8.1
Very good
4,401 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,401 reviews
Southwest
8.1
Very good
4,401 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,401 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,401 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,401 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 12 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 ($243), United Airlines ($244), and Delta ($247) offers the cheapest pricing from Greenville to Chicago. You may be able to fly from Greenville to Chicago for 24% 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 American Airlines, with whom users have recently found tickets for as low as $110. 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 Republic Airways (92%), Qatar Airways (91%) or Envoy Air (91%) 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 $989, our data shows the cheapest flight currently is $109. 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 February 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$313FlexibilityNo cancel feeOn-time71%
DeltaCheapest$228Average$355FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$241Average$379FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$304Average$402FlexibilityNo cancel feeOn-time63%
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