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Chesapeake

$169+ 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — RIC
Apr 25 — May 21
Sat 4/25
Sat 5/2
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 March 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/23. 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 3/304:07 pm
GSP
-
ORF
1 stop21h 24m
Multiple Airlines
Wed 4/13:28 pm
ORF
-
GSP
1 stop22h 02m
Multiple Airlines
Deal found 3/23$270
This United Airlines deal was found by Cheapflights users on 3/25. 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.
Thu 4/237:42 pm
GSP
-
ORF
1 stop3h 58m
United Airlines
Mon 4/276:11 am
ORF
-
GSP
1 stop3h 44m
United Airlines
Deal found 3/25$273
This American Airlines deal was found by Cheapflights users on 3/24. 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 5/76:30 am
GSP
-
ORF
1 stop3h 46m
American Airlines
Sat 5/97:58 pm
ORF
-
GSP
1 stop3h 59m
American Airlines
Deal found 3/24$274
This Southwest deal was found by Cheapflights users on 3/25. 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 4/255:25 pm
GSP
-
ORF
2 stops5h 40m
Southwest
Mon 4/275:25 pm
ORF
-
GSP
1 stop3h 30m
Southwest
Deal found 3/25$278
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 3/278:18 pm
GSP
-
ORF
1 stop18h 13m
Multiple Airlines
Mon 8/317:00 am
ORF
-
GSP
1 stop12h 33m
Multiple Airlines
Deal found 3/23$287
This Southwest deal was found by Cheapflights users on 3/23. 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 4/2512:25 pm
GSP
-
ORF
1 stop5h 45m
Southwest
Sun 5/310:00 am
ORF
-
GSP
1 stop3h 10m
Southwest
Deal found 3/23$310
This Southwest deal was found by Cheapflights users on 3/25. 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.
Thu 4/2312:35 pm
GSP
-
ORF
2 stops10h 20m
Southwest
Mon 4/275:25 pm
ORF
-
GSP
1 stop3h 30m
Southwest
Deal found 3/25$325
This American Airlines deal was found by Cheapflights users on 3/25. 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 4/189:05 am
GSP
-
ORF
1 stop5h 30m
American Airlines
Sun 4/195:00 am
ORF
-
GSP
1 stop3h 35m
American Airlines
Deal found 3/25$330
This Southwest deal was found by Cheapflights users on 3/25. 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.
Tue 4/2812:50 pm
GSP
-
ORF
2 stops9h 05m
Southwest
Thu 4/302:30 pm
ORF
-
GSP
1 stop6h 25m
Southwest
Deal found 3/25$333

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 March 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$270
(Delta)

One-way from

$169
(Kiwi.com)

Popular in

November

Cheapest in

October

Average price

$468
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. 10% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 26, 2026.
Use the filters below to find and compare flights from Greenville to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Tue 4/28

5:42 am-8:59 am

1 stop3h 17m

Norfolk

Thu 4/30

3:02 pm-9:43 pm

1 stop6h 41m

$270
Quickest round-trip

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Thu 4/23

7:42 pm-11:40 pm

1 stop3h 58m

Norfolk

Mon 4/27

6:11 am-9:55 am

1 stop3h 44m

$273

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Sat 4/25

12:25 pm-6:10 pm

1 stop5h 45m

Norfolk

Mon 4/27

5:25 pm-8:55 pm

1 stop3h 30m

$273

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Sat 4/25

12:25 pm-6:10 pm

1 stop5h 45m

Norfolk

Sun 5/3

10:00 am-1:10 pm

1 stop3h 10m

$310

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Mon 6/1

7:40 pm-11:44 pm

1 stop4h 04m

Norfolk

Thu 6/4

5:44 pm-11:29 pm

1 stop5h 45m

$343

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Sat 4/18

6:25 am-3:25 pm

2 stops9h 00m

Norfolk

Sun 4/19

10:00 am-1:10 pm

1 stop3h 10m

$346

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Mon 4/13

4:07 pm-1:31 pm

1 stop21h 24m

Norfolk

Thu 4/16

8:41 pm-7:38 pm

1 stop22h 57m

$349

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Wed 7/15

1:50 pm-6:20 pm

1 stop4h 30m

Norfolk

Mon 7/20

7:05 am-6:15 pm

2 stops11h 10m

$352

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Mon 8/10

8:40 am-5:55 pm

1 stop9h 15m

Norfolk

Thu 8/13

6:25 am-4:05 pm

2 stops9h 40m

$358
Cheapest one-way
Quickest one-way

GreenvilleNorfolk

GSP - ORF

GSPORF

Greenville

Mon 4/6

8:18 pm-9:47 pm

1 stop25h 29m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 11 resultsSorted by cheapest first
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, January is the cheapest month in which you can book a flight from Greenville to Chesapeake (average of $170). 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.

How much does it cost to fly round-trip from Greenville to Chesapeake?

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 March 26, 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
8,331 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.1

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
8,331 reviews
Delta
7.9
Good
8,331 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.1

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
7.1
Good
11,495 reviews
Delta
7.9
Good
8,331 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Comfort

7.9

Boarding

8.1

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 2 different airlines.

  • How long is the flight from Greenville to Chesapeake?

    There are many flights that can get you from Greenville to Chesapeake in 3h 17m. Fly via Delta, United Airlines, or Southwest 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, January is the cheapest month in which you can book a flight from Greenville to Chesapeake (average of $170). 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 2 airlines flying from Greenville to Chesapeake

Discover the top 2 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 March 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$310FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$196Average$413FlexibilityNo cancel feeOn-time71%

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