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$110+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — CHI
Jan 25 — Feb 11
Sat 1/25
Sat 2/1
1 adult, Economy
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The best prices from Greenville to Chicago are usually found in January or April, booked 48 days in advance, depart on a Thursday 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 January 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$274
(Southwest)

One-way from

$110
(American Airlines)

Popular in

September

Cheapest in

January

Average price

$288
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)
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High demand for flights, 0% potential price rise
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Best time to find cheap flights, 0% potential price drop
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Average for round-trip flights in January 2025
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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 January 20, 2025.

This Southwest deal was found by Cheapflights users on 1/20. 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.
Sat 2/1510:35 amGSP - MDW
2 stops10h 55mSouthwest
Wed 2/197:25 amMDW - GSP
1 stop7h 10mSouthwest
Deal found 1/20$274
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Fri 2/1412:45 pmGSP - ORD
Nonstop2h 05mAmerican Airlines
Mon 2/179:00 amORD - GSP
Nonstop1h 51mAmerican Airlines
Deal found 1/20$279
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Fri 2/146:30 amGSP - ORD
Nonstop2h 23mUnited Airlines
Sun 2/168:45 amORD - GSP
1 stop4h 31mUnited Airlines
Deal found 1/20$289
This Southwest deal was found by Cheapflights users on 1/18. 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 3/157:20 amGSP - ORD
1 stop6h 45mSouthwest
Tue 3/1811:25 amORD - GSP
1 stop8h 50mSouthwest
Deal found 1/18$298
This Delta deal was found by Cheapflights users on 1/20. 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 2/145:25 pmGSP - ORD
1 stop4h 28mDelta
Mon 2/174:58 pmORD - GSP
1 stop4h 01mDelta
Deal found 1/20$299
This Delta deal was found by Cheapflights users on 1/19. 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 2/215:40 amGSP - MDW
1 stop5h 32mDelta
Mon 2/242:08 pmMDW - GSP
1 stop6h 51mDelta
Deal found 1/19$299
This Mytrip deal was found by Cheapflights users on 1/18. 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.
Fri 1/315:08 pmGSP - ORD
1 stop7h 24mMultiple Airlines
Sun 2/26:06 pmORD - GSP
2 stops21h 12mMultiple Airlines
Deal found 1/18$322

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 January 20, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Sat 2/15

10:35 am-8:30 pm

2 stops10h 55m

Chicago Midway

Wed 2/19

7:25 am-3:35 pm

1 stop7h 10m

$274

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 2/14

12:45 pm-1:50 pm

Nonstop2h 05m

Chicago O'Hare Intl

Sun 2/16

9:00 am-11:51 am

Nonstop1h 51m

$279

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 2/14

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

Sun 2/16

8:45 am-2:16 pm

1 stop4h 31m

$289

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Sat 3/15

7:20 am-1:05 pm

1 stop6h 45m

Chicago O'Hare Intl

Tue 3/18

11:25 am-9:15 pm

1 stop8h 50m

$298

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 2/14

5:25 pm-8:53 pm

1 stop4h 28m

Chicago O'Hare Intl

Mon 2/17

4:58 pm-9:59 pm

1 stop4h 01m

$299

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Fri 2/21

5:40 am-10:12 am

1 stop5h 32m

Chicago Midway

Sun 2/23

6:00 am-11:09 am

1 stop4h 09m

$299

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Fri 1/31

5:08 pm-11:32 pm

1 stop7h 24m

Chicago O'Hare Intl

Sun 2/2

6:06 pm-4:18 pm

2 stops21h 12m

$322

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Wed 3/19

8:00 am-9:10 am

Nonstop2h 10m

$110

GreenvilleChicago

GSP - ORD

GSPORD

Greenville

Tue 2/18

6:00 am-1:44 pm

1 stop8h 44m

$120

GreenvilleChicago

GSP - MDW

GSPMDW

Greenville

Wed 3/26

7:30 am-12:36 pm

1 stop6h 06m

$120

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 14 results
1
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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
eDreamsPrice 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 January 17, 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 $320). 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 20, 2025.

It’s typically best to fly out from Greenville to Chicago at noon. Doing so could potentially save you 14% on the flight price compared to flying in the evening, 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 Thursday at noon when fares are most often at their lowest. Monday 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 20, 2025.

The most flights from GSP to CHI are scheduled on a Monday (13 on average). You will have fewer flight options on Sunday, 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 January 20, 2025.
Read reviews from past customers who have flown United Airlines, Delta and Southwest 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
4,659 reviews

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,982 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 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.

  • What are the cheapest airlines flying from Greenville to Chicago round-trip?

    According to our current data, Southwest ($274), American Airlines ($279), and United Airlines ($289) offers the cheapest pricing from Greenville to Chicago. You may be able to fly from Greenville to Chicago for 13% 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 United Airlines, 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 Avianca (87%), Republic Airways (87%) or Qatar Airways (87%) 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 $1,262, our data shows the cheapest flight currently is $139. When looking at the most popular route, (Greenville - Chicago O'Hare Intl), you can expect to pay $239 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 $320). 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 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$310FlexibilityNo cancel feeOn-time71%
DeltaCheapest$217Average$355FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$240Average$371FlexibilityNo cancel feeOn-time69%
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