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$337+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
PGV — CHI
May 17 — May 241
Sun 5/17
Sun 5/24
1 adult, Economy
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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 April 17, 2026.

This American Airlines deal was found by Cheapflights users on 4/15. 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 5/265:10 am
PGV
-
ORD
1 stop4h 52m
American Airlines
Thu 6/45:10 am
ORD
-
PGV
1 stop4h 26m
American Airlines
Deal found 4/15$337
This American Airlines deal was found by Cheapflights users on 4/13. 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 4/287:13 pm
PGV
-
ORD
1 stop5h 41m
American Airlines
Sat 5/26:41 pm
ORD
-
PGV
1 stop4h 15m
American Airlines
Deal found 4/13$509
This American Airlines deal was found by Cheapflights users on 4/15. 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.
Sat 4/1812:54 pm
PGV
-
ORD
1 stop4h 27m
American Airlines
Sun 4/263:26 pm
ORD
-
PGV
1 stop7h 30m
American Airlines
Deal found 4/15$604
This American Airlines deal was found by Cheapflights users on 4/14. 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 4/2912:54 pm
PGV
-
ORD
2 stops7h 14m
American Airlines
Sun 5/34:00 pm
ORD
-
PGV
2 stops6h 56m
American Airlines
Deal found 4/14$748
This American Airlines deal was found by Cheapflights users on 4/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:00 pm
PGV
-
ORD
1 stop15h 11m
American Airlines
Fri 5/18:46 pm
ORD
-
PGV
1 stop14h 42m
American Airlines
Deal found 4/12$840
This American Airlines deal was found by Cheapflights users on 4/16. 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 5/112:54 pm
PGV
-
ORD
1 stop4h 27m
American Airlines
Tue 5/511:09 am
ORD
-
PGV
2 stops6h 39m
American Airlines
Deal found 4/16$886
This American Airlines deal was found by Cheapflights users on 4/15. 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.
Thu 4/3012:54 pm
PGV
-
ORD
2 stops7h 14m
American Airlines
Mon 5/44:00 pm
ORD
-
PGV
2 stops6h 56m
American Airlines
Deal found 4/15$929

Find 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 April 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$337
(American Airlines)
Provider with most accurate pricing for Pitt-Greenville-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pitt-Greenville-Chicago (CHI) flights.
Search Deals
From Pitt-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 April 17, 2026.
Use the filters below to find and compare flights from Greenville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Tue 5/26

5:10 am-9:02 am

1 stop4h 52m

Chicago O'Hare Intl

Thu 6/4

5:10 am-10:36 am

1 stop4h 26m

$337

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Fri 5/1

12:54 pm-4:21 pm

1 stop4h 27m

Chicago O'Hare Intl

Tue 5/5

3:26 pm-10:58 pm

1 stop6h 32m

$509

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Tue 4/28

7:13 pm-11:54 pm

1 stop5h 41m

Chicago O'Hare Intl

Sat 5/2

6:41 pm-11:56 pm

1 stop4h 15m

$509

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Wed 4/29

12:54 pm-7:08 pm

2 stops7h 14m

Chicago O'Hare Intl

Sun 5/3

6:05 am-12:28 pm

1 stop5h 23m

$514

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Thu 4/30

8:00 pm-11:54 pm

1 stop4h 54m

Chicago O'Hare Intl

Mon 5/4

4:00 pm-11:56 pm

2 stops6h 56m

$514

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Mon 4/27

8:00 pm-10:11 am

1 stop15h 11m

Chicago O'Hare Intl

Fri 5/1

8:46 pm-12:28 pm

1 stop14h 42m

$840
Cheapest one-way
Quickest one-way

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Sun 5/10

8:00 pm-11:54 pm

1 stop4h 54m

$526

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Thu 5/28

11:03 am-3:59 pm

1 stop5h 56m

$526

GreenvilleChicago

PGV - ORD

PGVORD

Pitt-Greenville

Fri 6/26

11:03 am-5:42 pm

1 stop7h 39m

$546

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

Sorted by cheapest first

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 April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice 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, North Carolina-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Greenville, North Carolina-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Greenville, North Carolina-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Greenville, North Carolina-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, North Carolina-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
No data available for this route at this time. Please check back soon.

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 0 different airlines.

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

    A quick flight from Greenville, North Carolina to Chicago can take about 4h 52m. American Airlines provides one of the quickest options available for as low as $337. 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.

See more FAQs

Traveling to a place near Chicago?

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