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$433+ Cheap flights from Greenville, NC (PGV) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
PGV — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Greenville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Greenville (PGV) 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 September 16, 2025.

Round-trip from

$433
(American Airlines)
From Pitt-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 September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 9/2712:51 pmPGV - ORD
1 stop6h 43mAmerican Airlines
Tue 10/79:20 amORD - PGV
1 stop5h 18mAmerican Airlines
Deal found 9/14$433
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:00 amPGV - ORD
1 stop5h 43mAmerican Airlines
Sat 10/48:37 amORD - PGV
1 stop7h 05mAmerican Airlines
Deal found 9/15$443
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 9/175:07 pmPGV - ORD
2 stops7h 41mAmerican Airlines
Sat 9/205:00 amORD - PGV
1 stop6h 24mAmerican Airlines
Deal found 9/14$448
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 9/265:07 pmPGV - ORD
1 stop7h 05mAmerican Airlines
Mon 9/297:02 amORD - PGV
1 stop4h 22mAmerican Airlines
Deal found 9/14$499
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 9/276:00 amPGV - ORD
1 stop6h 30mAmerican Airlines
Sun 10/55:00 amORD - PGV
1 stop4h 33mAmerican Airlines
Deal found 9/14$503
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 11/2610:56 amPGV - ORD
1 stop6h 09mAmerican Airlines
Sat 11/296:35 pmORD - PGV
1 stop4h 24mAmerican Airlines
Deal found 9/14$510
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 9/276:00 amPGV - ORD
2 stops6h 06mAmerican Airlines
Mon 10/611:13 amORD - PGV
2 stops12h 00mAmerican Airlines
Deal found 9/14$513

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 September 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

PGV - ORD

PGVORD

Pitt-Greenville

Sat 9/27

12:51 pm-6:34 pm

1 stop6h 43m

Chicago O'Hare Intl

Tue 10/7

9:20 am-3:38 pm

1 stop5h 18m

$433

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Tue 9/30

12:51 pm-5:30 pm

1 stop5h 39m

Chicago O'Hare Intl

Wed 10/8

6:45 am-3:22 pm

2 stops7h 37m

$438

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Fri 9/26

5:07 pm-11:12 pm

1 stop7h 05m

Chicago O'Hare Intl

Mon 9/29

7:02 am-12:24 pm

1 stop4h 22m

$499

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Sat 9/27

6:00 am-11:30 am

1 stop6h 30m

Chicago O'Hare Intl

Sun 10/5

5:00 am-10:33 am

1 stop4h 33m

$503

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Sat 9/27

6:00 am-1:42 pm

2 stops8h 42m

Chicago O'Hare Intl

Thu 10/9

5:22 am-10:34 am

1 stop4h 12m

$508

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Sat 9/27

5:07 pm-11:12 pm

1 stop7h 05m

Chicago O'Hare Intl

Mon 10/6

6:00 am-2:44 pm

2 stops7h 44m

$508

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Sat 9/27

12:51 pm-6:34 pm

1 stop6h 43m

Chicago O'Hare Intl

Wed 10/8

6:00 am-3:22 pm

2 stops8h 22m

$508

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Wed 11/26

10:56 am-4:05 pm

1 stop6h 09m

Chicago O'Hare Intl

Sat 11/29

6:35 pm-11:59 pm

1 stop4h 24m

$510

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Fri 9/26

6:00 am-11:30 am

1 stop6h 30m

$466

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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

What is the cheapest month to book a flight from Greenville, North Carolina to Chicago?

Currently, August is the cheapest month in which you can book a flight from Greenville, North Carolina to Chicago (average of $245). Flying from Greenville, North Carolina 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.

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 September 16, 2025.
Peruse reviews from past customers who have flown with American Airlines from Greenville to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Crew

8.0

Food

6.4

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Crew

8.0

Food

6.4

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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?

    If you book a flight to Chicago from Greenville, you will be flying from Pitt-Greenville, which is the city’s only airport. Pitt-Greenville (PGV) is located 1.7 mi from the center of Greenville. There are 0 flights from Pitt-Greenville to Chicago per day from 1 airline.

  • How long is the flight from Greenville, North Carolina to Chicago?

    A quick flight from Greenville, North Carolina to Chicago can take about 6h 43m. American Airlines provides one of the quickest options available for as low as $433. The distance from Greenville, North Carolina to Chicago is about 715 mi.

  • 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, North Carolina to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Greenville, North Carolina to Chicago (average of $245). Flying from Greenville, North Carolina 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 airline flying from Greenville to Chicago

Discover the top airline 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$316Average$386FlexibilityNo cancel feeOn-time71%

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