$131+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — RIC
Sep 12 — Sep 191
Round-trip
1 adult, Economy
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Find cheap flights from Greenville to Chesapeake with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Greenville to Chesapeake
Cheapest
Best
Last-minute
One-way
Cheapest flights from Greenville to ChesapeakeExplore 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 August 13, 2026.
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 August 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/103:52 pm -
1 stop26h 56m
Wed 9/167:43 pm -
1 stop24h 06m
Deal found 8/11![Multiple Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 8/318:45 pm -
1 stop19h 26m
Wed 9/97:43 pm -
1 stop24h 06m
Deal found 8/10![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 8/318:45 pm -
1 stop19h 26m
Sat 9/124:45 pm -
2 stops42h 46m
Deal found 8/10![Multiple Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:05 am -
1 stop6h 01m
Tue 9/226:40 am -
1 stop6h 10m
Deal found 8/12![Delta logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 8/318:45 pm -
1 stop19h 26m
Thu 9/104:57 pm -
1 stop19h 53m
Deal found 8/10![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Wed 9/168:24 pm -
2 stops16h 05m
Wed 9/237:43 pm -
1 stop26h 07m
Deal found 8/11![Multiple Airlines logo]()
$236
This Southwest deal was found by Cheapflights users on 8/10. 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 9/167:00 am -
2 stops8h 55m
Tue 9/2212:40 pm -
1 stop4h 05m
Deal found 8/10![Southwest logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/103:52 pm -
1 stop26h 56m
Mon 9/1411:22 am -
1 stop24h 27m
Deal found 8/10![Multiple Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Tue 9/111:07 am -
2 stops25h 18m
Wed 9/97:43 pm -
1 stop24h 06m
Deal found 8/10![Multiple Airlines logo]()
$242
Best flights from Greenville to ChesapeakeDiscover carefully curated flight deals from Greenville to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
Discover carefully curated flight deals from Greenville to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:05 am -
1 stop6h 01m
Tue 9/226:40 am -
1 stop6h 10m
Deal found 8/12![Delta logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:24 pm -
2 stops16h 05m
Wed 9/237:43 pm -
1 stop26h 07m
Deal found 8/13![Multiple Airlines logo]()
$236
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:00 am -
2 stops8h 55m
Tue 9/223:20 pm -
1 stop4h 10m
Deal found 8/12![Southwest logo]()
$238
This Southwest deal was found by Cheapflights users on 8/10. 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 9/158:15 am -
2 stops9h 05m
Tue 9/228:50 am -
2 stops7h 55m
Deal found 8/10![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 8/10. 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 9/27:00 am -
2 stops7h 30m
Thu 9/103:45 pm -
1 stop4h 35m
Deal found 8/10![Southwest logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 9/1010:07 am -
1 stop12h 49m
Sun 9/131:18 pm -
2 stops25h 10m
Deal found 8/9![Multiple Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 8/11. 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 9/45:46 am -
1 stop3h 27m
Sun 9/66:00 am -
1 stop3h 28m
Deal found 8/11![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:04 pm -
1 stop5h 41m
Sun 10/185:30 am -
1 stop3h 53m
Deal found 8/12![Delta logo]()
$326
Last-minute flights from Greenville to ChesapeakeDiscover last-minute flight deals from Greenville to Chesapeake. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Greenville to Chesapeake. Data last updated August 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 8/318:45 pm -
1 stop19h 26m
Wed 9/97:43 pm -
1 stop24h 06m
Deal found 8/10![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 8/318:45 pm -
1 stop19h 26m
Sat 9/124:45 pm -
2 stops42h 46m
Deal found 8/10![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 8/318:45 pm -
1 stop19h 26m
Thu 9/104:57 pm -
1 stop19h 53m
Deal found 8/10![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Tue 9/111:07 am -
2 stops25h 18m
Wed 9/97:43 pm -
1 stop24h 06m
Deal found 8/10![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/103:52 pm -
1 stop26h 56m
Wed 9/167:43 pm -
1 stop24h 06m
Deal found 8/11![Multiple Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/103:52 pm -
1 stop26h 56m
Mon 9/1411:22 am -
1 stop24h 27m
Deal found 8/10![Multiple Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:05 am -
1 stop6h 01m
Tue 9/226:40 am -
1 stop6h 10m
Deal found 8/12![Delta logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Wed 9/168:24 pm -
2 stops16h 05m
Wed 9/237:43 pm -
1 stop26h 07m
Deal found 8/11![Multiple Airlines logo]()
$236
This Southwest deal was found by Cheapflights users on 8/10. 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 9/167:00 am -
2 stops8h 55m
Tue 9/2212:40 pm -
1 stop4h 05m
Deal found 8/10![Southwest logo]()
$238
One-way flights from Greenville to ChesapeakeSearch for one-way flight options from Greenville to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
Search for one-way flight options from Greenville to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Wed 9/168:24 pm -
2 stops16h 05m
Deal found 8/9![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 10/238:32 pm -
2 stops15h 30m
Deal found 8/9![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Wed 9/168:24 pm -
1 stop26h 32m
Deal found 8/9![Breeze Airways logo]()
$140
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 August 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (Kiwi.com) |
One-way from | $131 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $401 |
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 August 13, 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
Cheapest round-trip
GreenvilleNorfolk
GSP Greenville - ORF Norfolk
GSPORF
Greenville
Wed 9/16
8:05 am-2:06 pm
1 stop6h 01m
Norfolk
Tue 9/22
6:40 am-12:50 pm
1 stop6h 10m
$233
GreenvilleNorfolk
GSP Greenville - ORF Norfolk
GSPORF
Greenville
Wed 9/16
8:24 pm-12:29 pm
2 stops16h 05m
Norfolk
Wed 9/23
7:43 pm-9:50 pm
1 stop26h 07m
$236
GreenvilleNorfolk
GSP Greenville - ORF Norfolk
GSPORF
Greenville
Wed 9/16
7:00 am-3:55 pm
2 stops8h 55m
Norfolk
Tue 9/22
3:20 pm-7:30 pm
1 stop4h 10m
$238
GreenvilleNorfolk
GSP Greenville - ORF Norfolk
GSPORF
Greenville
Tue 9/15
8:15 am-5:20 pm
2 stops9h 05m
Norfolk
Tue 9/22
8:50 am-4:45 pm
2 stops7h 55m
$243
GreenvilleNorfolk
GSP Greenville - ORF Norfolk
GSPORF
Greenville
Wed 9/2
7:00 am-2:30 pm
2 stops7h 30m
Norfolk
Thu 9/10
3:45 pm-8:20 pm
1 stop4h 35m
$252
GreenvilleNorfolk
GSP Greenville - ORF Norfolk
GSPORF
Greenville
Thu 9/10
10:07 am-10:56 pm
1 stop12h 49m
Norfolk
Sun 9/13
1:18 pm-2:28 pm
2 stops25h 10m
$303
Quickest round-trip
GreenvilleNorfolk
GSP Greenville - ORF Norfolk
GSPORF
Greenville
Fri 9/4
5:46 am-9:13 am
1 stop3h 27m
Norfolk
Sun 9/6
6:00 am-9:28 am
1 stop3h 28m
$309
GreenvilleNorfolk
GSP Greenville - ORF Norfolk
GSPORF
Greenville
Fri 10/16
7:04 pm-12:45 am
1 stop5h 41m
Norfolk
Sun 10/18
5:30 am-9:23 am
1 stop3h 53m
$326
Cheapest one-way
Quickest one-way
GreenvilleNorfolk
GSP Greenville - ORF Norfolk
GSPORF
Greenville
Fri 10/23
8:32 pm-12:02 pm
2 stops15h 30m
$138
GreenvilleNorfolk
GSP Greenville - ORF Norfolk
GSPORF
Greenville
Fri 10/23
8:47 pm-6:03 pm
3 stops21h 16m
$170
Sorted by cheapest first
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.
GSP-ORF
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
GSP-C6E
GSP-ORF
No data available for this route at this time. Please check back soon.
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 August 13, 2026.
Get a feel of what it's like to fly with 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.
Boarding
7.5
Food
6.4
Comfort
7.2
Crew
7.9
Overall
7.1
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
Boarding
7.5
Food
6.4
Comfort
7.2
Crew
7.9
Overall
7.1
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
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.
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Alternative routes for Greenville to Chesapeake
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Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Greenville to Chesapeake by cabin class
Find flights from Greenville to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Greenville and Chesapeake flights
Browse other Greenville and Chesapeake flight options. Last updated on August 13, 2026.
Other flights from Greenville
Browse through other flights departing from Greenville. Flights are based on user searches made on Cheapflights and were last updated on August 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Greenville to Chesapeake flights
Consider these flights traveling from Greenville to Chesapeake.
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 August 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$240 | Average$381 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$275 | Average$336 | FlexibilityNo cancel fee | On-timeN/A |