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Chesapeake

$164+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — RIC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:53 pm
GSP
-
ORF
1 stop8h 57m
Multiple Airlines
Thu 2/267:31 pm
ORF
-
GSP
1 stop22h 28m
Multiple Airlines
Deal found 1/28$208
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Sat 2/2110:00 am
GSP
-
ORF
1 stop4h 03m
United Airlines
Mon 2/236:00 am
ORF
-
GSP
1 stop5h 21m
United Airlines
Deal found 1/28$267
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/68:18 pm
GSP
-
ORF
1 stop18h 13m
Multiple Airlines
Sun 3/158:41 pm
ORF
-
GSP
1 stop20h 34m
Multiple Airlines
Deal found 1/27$278
This Southwest deal was found by Cheapflights users on 1/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2110:35 am
GSP
-
ORF
2 stops6h 35m
Southwest
Mon 2/234:40 pm
ORF
-
GSP
1 stop3h 40m
Southwest
Deal found 1/28$284
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:00 am
GSP
-
ORF
1 stop4h 05m
Delta
Mon 2/235:25 am
ORF
-
GSP
1 stop3h 40m
Delta
Deal found 1/28$299
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:01 pm
GSP
-
ORF
1 stop4h 20m
Delta
Sun 3/15:25 am
ORF
-
GSP
1 stop5h 48m
Delta
Deal found 1/28$303
This Delta deal was found by Cheapflights users on 1/27. 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.
Wed 2/115:40 am
GSP
-
ORF
1 stop3h 30m
Delta
Sun 2/155:25 am
ORF
-
GSP
1 stop3h 40m
Delta
Deal found 1/27$319
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:07 pm
GSP
-
ORF
1 stop21h 24m
Breeze Airways
Thu 5/78:26 pm
ORF
-
GSP
1 stop12h 52m
Breeze Airways
Deal found 1/27$320
This Delta deal was found by Cheapflights users on 1/27. 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.
Mon 7/136:45 am
GSP
-
ORF
1 stop6h 04m
Delta
Thu 7/164:27 pm
ORF
-
GSP
1 stop4h 58m
Delta
Deal found 1/27$327

Find flight deals from Greenville to Chesapeake

Keep the following information in mind while searching for Greenville to Chesapeake flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$208
(Kiwi.com)

One-way from

$164
(Delta)

Popular in

March

Cheapest in

October

Average price

$292
Provider with most accurate pricing for Greenville-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Greenville-Norfolk flights.
Search Deals
From Greenville to Chesapeake
Search Deals
One-way flight from Greenville to Chesapeake
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Thu 2/19

3:04 pm-10:37 am

2 stops19h 33m

Norfolk

Thu 2/26

7:31 pm-5:59 pm

1 stop22h 28m

$236

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Sat 2/21

10:00 am-2:03 pm

1 stop4h 03m

Norfolk

Mon 2/23

6:00 am-11:21 am

1 stop5h 21m

$267

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Fri 3/6

8:18 pm-2:31 pm

1 stop18h 13m

Norfolk

Sun 3/15

8:41 pm-5:15 pm

1 stop20h 34m

$278

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Sat 2/21

10:35 am-5:10 pm

2 stops6h 35m

Norfolk

Mon 2/23

4:40 pm-8:20 pm

1 stop3h 40m

$284

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Thu 2/26

6:01 pm-10:21 pm

1 stop4h 20m

Norfolk

Sun 3/1

5:25 am-11:13 am

1 stop5h 48m

$303

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Wed 2/11

5:40 am-9:10 am

1 stop3h 30m

Norfolk

Sun 2/15

5:25 am-9:05 am

1 stop3h 40m

$319

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Mon 5/4

4:07 pm-1:31 pm

1 stop21h 24m

Norfolk

Thu 5/7

8:26 pm-9:18 am

1 stop12h 52m

$320

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Mon 7/13

6:45 am-12:49 pm

1 stop6h 04m

Norfolk

Thu 7/16

4:27 pm-9:25 pm

1 stop4h 58m

$327

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Thu 3/19

1:55 pm-6:40 pm

1 stop4h 45m

Norfolk

Sat 3/21

9:50 am-1:15 pm

1 stop3h 25m

$347

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Thu 3/12

8:30 am-12:34 pm

1 stop4h 04m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 15 results
1
2

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, September is the cheapest month in which you can book a flight from Greenville to Chesapeake (average of $176). Flying from Greenville to Chesapeake in November is currently the most expensive (average of $242). 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 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 January 29, 2026.
Get a feel of what it's like to fly with Delta and American 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.
Delta
7.9
Good
8,128 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,128 reviews
Delta
7.9
Good
8,128 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,205 reviews
Delta
7.9
Good
8,128 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Greenville to Chesapeake?

    There are many flights that can get you from Greenville to Chesapeake in 4h 03m. Fly via United Airlines, Southwest, or Delta to get the fastest option. The distance between Greenville and Chesapeake is about 364 mi. This flight may include one or multiple stops.

  • 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, September is the cheapest month in which you can book a flight from Greenville to Chesapeake (average of $176). Flying from Greenville to Chesapeake in November is currently the most expensive (average of $242). 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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Alternative routes for Greenville to Chesapeake

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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$348FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$196Average$409FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$228Average$276FlexibilityNo cancel feeOn-time63%

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