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Chesapeake

$99+ Cheap flights from Greenville (GSP) to Chesapeake, VA

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — RIC
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheap flight deals from Greenville to Chesapeake

Keep the following information in mind while searching for Greenville to Chesapeake flight deals. Data was last updated July 29, 2025.

Round-trip from

$197
(Delta)

One-way from

$99
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$336
From Greenville to Chesapeake
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One-way flight from Greenville to Chesapeake
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Highest demand for flights based on searches. 18% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Greenville to Chesapeake

Cheapest flights from Greenville to Chesapeake
Explore the most affordable flight options available from Greenville to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/266:30 amGSP - ORF
1 stop4h 08mDelta
Tue 9/25:30 amORF - GSP
1 stop5h 59mDelta
Deal found 7/27$197
This American Airlines deal was found by Cheapflights users on 7/29. 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 10/306:11 amGSP - ORF
1 stop5h 54mAmerican Airlines
Fri 10/312:10 pmORF - GSP
1 stop4h 27mAmerican Airlines
Deal found 7/29$258
This Southwest deal was found by Cheapflights users on 7/27. 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.
Wed 10/86:05 amGSP - ORF
1 stop3h 05mSouthwest
Tue 10/219:45 amORF - GSP
2 stops8h 45mSouthwest
Deal found 7/27$259
This Mytrip deal was found by Cheapflights users on 7/29. 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 8/74:33 pmGSP - ORF
2 stops24h 48mMultiple Airlines
Sun 8/105:50 amORF - GSP
1 stop8h 39mMultiple Airlines
Deal found 7/29$400
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/55:52 pmGSP - ORF
2 stops20h 02mUnited Airlines
Sun 9/710:30 amORF - GSP
1 stop3h 42mUnited Airlines
Deal found 7/28$466

Cheapflights Fare Finder

 
Customize your flight search to find flights from Greenville to Chesapeake 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 July 29, 2025.
Use the filters below to find and compare flights from Greenville to Chesapeake that are best for you.

Fly from

Greenville

Fly to

Chesapeake

Route

Depart

Return

Price

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Tue 8/26

6:30 am-10:38 am

1 stop4h 08m

Norfolk

Tue 9/2

5:30 am-11:29 am

1 stop5h 59m

$197

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Thu 10/30

6:11 am-12:05 pm

1 stop5h 54m

Norfolk

Fri 10/31

2:10 pm-6:37 pm

1 stop4h 27m

$258

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Wed 10/8

6:05 am-9:10 am

1 stop3h 05m

Norfolk

Tue 10/21

9:45 am-6:30 pm

2 stops8h 45m

$259

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Fri 9/5

5:52 pm-1:54 pm

2 stops20h 02m

Norfolk

Sun 9/7

10:30 am-2:12 pm

1 stop3h 42m

$466

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Fri 8/8

2:50 pm-10:35 pm

1 stop7h 45m

Norfolk

Sun 8/10

9:05 am-8:48 am

2 stops23h 43m

$497

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Tue 10/14

11:20 am-5:30 pm

1 stop6h 10m

$99

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Tue 10/14

6:05 am-2:20 pm

2 stops8h 15m

$199

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Fri 9/19

8:46 pm-10:48 pm

3 stops26h 02m

$286

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Tue 10/14

5:00 pm-10:42 am

3 stops17h 42m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Best time to book a flight from Greenville to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake 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 Chesapeake

What is the cheapest month to book a flight from Greenville to Chesapeake?

Currently, January is the cheapest month in which you can book a flight from Greenville to Chesapeake (average of $281). Flying from Greenville to Chesapeake in March is currently the most expensive (average of $351). 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 C6E?

Find hourly flight availability from Greenville to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2025.

When flying from Greenville to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Use this chart to determine the cheapest time to fly round-trip from Greenville to Chesapeake. Price data was last updated on December 16, 2024.

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

Reviews of airlines servicing Chesapeake

Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated July 29, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Greenville to Chesapeake by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Greenville to Chesapeake. 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 Chesapeake?

    If you book a flight to Chesapeake from Greenville, you will be flying from Greenville, which is the city’s only airport. Greenville (GSP) is located 10.4 mi from the center of Greenville. There are 0 flights from Greenville to Chesapeake per day from 3 different airlines.

  • What are the cheapest airlines to fly from Greenville to Chesapeake one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $99. Users have also found prices from $199 and $363 on Southwest and United Airlines, respectively.

  • Can I find deals for flights from Greenville to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Greenville to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Greenville to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Greenville to Chesapeake.

  • Can I find deals for business class flights from Greenville to Chesapeake?

    Yes. Cheapflights offers flight deals from Greenville to Chesapeake 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 Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from Greenville to Chesapeake (average of $281). Flying from Greenville to Chesapeake in March is currently the most expensive (average of $351). 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

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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 Chesapeake

Discover the top 3 airlines that operate flights from Greenville to Chesapeake. 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$210Average$404FlexibilityNo cancel feeOn-time71%
DeltaCheapest$227Average$351FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$232Average$312FlexibilityNo cancel feeOn-time63%

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