$126+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — RIC
Jul 27 — Aug 31
Round-trip
1 adult, Economy
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Find cheap flights from Greenville to Chesapeake with Cheapflights
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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
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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
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Best
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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 June 27, 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 June 27, 2026.
This United Airlines deal was found by Cheapflights users on 6/26. 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 8/2010:25 am
GSP
- ORF
1 stop3h 50m
United Airlines
Mon 8/246:15 am
ORF
- GSP
1 stop3h 35m
United Airlines
Deal found 6/26![United Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 6/25. 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 9/811:00 am
GSP
- ORF
2 stops9h 50m
Southwest
Thu 9/1010:10 am
ORF
- GSP
1 stop5h 55m
Southwest
Deal found 6/25![Southwest logo]()
$270
This United Airlines deal was found by Cheapflights users on 6/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:40 pm
GSP
- ORF
1 stop4h 04m
United Airlines
Wed 8/510:45 am
ORF
- GSP
1 stop3h 35m
United Airlines
Deal found 6/23![United Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/144:57 pm
GSP
- ORF
2 stops18h 24m
Multiple Airlines
Sat 8/159:34 pm
ORF
- GSP
1 stop9h 54m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 6/22. 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 11/55:40 am
GSP
- ORF
1 stop5h 53m
Delta
Sat 11/76:55 am
ORF
- GSP
1 stop6h 13m
Delta
Deal found 6/22![Delta logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:25 am
GSP
- ORF
1 stop12h 14m
Multiple Airlines
Thu 7/3012:10 pm
ORF
- GSP
2 stops19h 20m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$284
This Southwest deal was found by Cheapflights users on 6/22. 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 11/510:45 am
GSP
- ORF
1 stop4h 00m
Southwest
Sat 11/76:15 am
ORF
- GSP
2 stops9h 45m
Southwest
Deal found 6/22![Southwest logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:13 pm
GSP
- ORF
2 stops16h 12m
Multiple Airlines
Mon 9/77:00 am
ORF
- GSP
1 stop12h 33m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 6/26. 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 8/204:40 pm
GSP
- ORF
1 stop4h 55m
Southwest
Mon 8/248:00 am
ORF
- GSP
2 stops8h 05m
Southwest
Deal found 6/26![Southwest logo]()
$294
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 June 27, 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 June 27, 2026.
This Southwest deal was found by Cheapflights users on 6/26. 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 11/58:15 am
GSP
- ORF
1 stop3h 20m
Southwest
Sat 11/76:15 am
ORF
- GSP
1 stop3h 55m
Southwest
Deal found 6/26![Southwest logo]()
$265
This United Airlines deal was found by Cheapflights users on 6/26. 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.
Tue 10/66:20 am
GSP
- ORF
1 stop5h 55m
United Airlines
Wed 10/76:00 am
ORF
- GSP
1 stop4h 45m
United Airlines
Deal found 6/26![United Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 6/25. 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 9/81:20 pm
GSP
- ORF
1 stop7h 30m
Southwest
Thu 9/1010:10 am
ORF
- GSP
1 stop5h 55m
Southwest
Deal found 6/25![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 6/26. 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 11/58:15 am
GSP
- ORF
1 stop3h 20m
Southwest
Sun 11/86:15 am
ORF
- GSP
1 stop3h 55m
Southwest
Deal found 6/26![Southwest logo]()
$306
This United Airlines deal was found by Cheapflights users on 6/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/117:47 pm
GSP
- ORF
1 stop3h 56m
United Airlines
Wed 8/126:10 pm
ORF
- GSP
1 stop5h 01m
United Airlines
Deal found 6/23![United Airlines logo]()
$343
This United Airlines deal was found by Cheapflights users on 6/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:40 pm
GSP
- ORF
1 stop4h 04m
United Airlines
Wed 8/126:00 am
ORF
- GSP
1 stop4h 37m
United Airlines
Deal found 6/24![United Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 6/23. 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 7/256:55 am
GSP
- ORF
1 stop8h 20m
Southwest
Wed 8/512:15 pm
ORF
- GSP
2 stops8h 40m
Southwest
Deal found 6/23![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 6/22. 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.
Fri 8/141:05 pm
GSP
- ORF
2 stops8h 30m
Southwest
Sat 8/156:25 am
ORF
- GSP
2 stops8h 30m
Southwest
Deal found 6/22![Southwest logo]()
$343
Last-minute flights from Greenville to ChesapeakeDiscover last-minute flight deals from Greenville to Chesapeake. Data last updated June 27, 2026 and is based on user searches.
Discover last-minute flight deals from Greenville to Chesapeake. Data last updated June 27, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:25 am
GSP
- ORF
1 stop12h 14m
Multiple Airlines
Sun 7/199:34 pm
ORF
- GSP
1 stop9h 56m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:25 am
GSP
- ORF
1 stop12h 14m
Multiple Airlines
Thu 7/3012:10 pm
ORF
- GSP
2 stops19h 20m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 6/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/235:44 am
GSP
- ORF
1 stop3h 25m
Delta
Mon 7/276:17 pm
ORF
- GSP
1 stop4h 38m
Delta
Deal found 6/25![Delta logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/233:40 pm
GSP
- ORF
1 stop8h 13m
Multiple Airlines
Mon 7/2712:10 pm
ORF
- GSP
2 stops26h 56m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 6/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:40 pm
GSP
- ORF
1 stop4h 04m
United Airlines
Wed 8/510:45 am
ORF
- GSP
1 stop3h 35m
United Airlines
Deal found 6/23![United Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 6/23. 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 7/256:55 am
GSP
- ORF
1 stop8h 20m
Southwest
Wed 8/512:15 pm
ORF
- GSP
2 stops8h 40m
Southwest
Deal found 6/23![Southwest logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 7/278:20 am
GSP
- ORF
1 stop12h 19m
Multiple Airlines
Fri 7/3112:10 pm
ORF
- GSP
2 stops43h 25m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 6/22. 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.
Mon 7/278:30 am
GSP
- ORF
1 stop3h 10m
Southwest
Fri 7/314:30 pm
ORF
- GSP
1 stop5h 10m
Southwest
Deal found 6/22![Southwest logo]()
$347
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 June 27, 2026.
Search for one-way flight options from Greenville to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/104:57 pm
GSP
- ORF
2 stops24h 35m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/108:13 pm
GSP
- ORF
3 stops21h 19m
Breeze Airways
Deal found 6/22![Breeze Airways logo]()
$134
This American Airlines deal was found by Cheapflights users on 6/22. 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 7/47:00 am
GSP
- ORF
1 stop3h 35m
American Airlines
Deal found 6/22![American Airlines logo]()
$154
This Southwest deal was found by Cheapflights users on 6/22. 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 7/46:45 am
GSP
- ORF
2 stops8h 25m
Southwest
Deal found 6/22![Southwest logo]()
$159
This Delta deal was found by Cheapflights users on 6/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/277:44 pm
GSP
- ORF
1 stop5h 01m
Delta
Deal found 6/24![Delta logo]()
$174
This Southwest deal was found by Cheapflights users on 6/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2712:55 pm
GSP
- ORF
2 stops9h 10m
Southwest
Deal found 6/24![Southwest logo]()
$179
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 June 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $265 (Southwest) |
One-way from | $126 (Kiwi.com) |
Popular in | May |
Cheapest in | February |
Average price | $416 |
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 June 27, 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
Quickest round-trip
GreenvilleNorfolk
GSP - ORF
GSPORF
Greenville
Thu 11/5
8:15 am-11:35 am
1 stop3h 20m
Norfolk
Sat 11/7
6:15 am-10:10 am
1 stop3h 55m
$265
GreenvilleNorfolk
GSP - ORF
GSPORF
Greenville
Tue 9/8
1:20 pm-8:50 pm
1 stop7h 30m
Norfolk
Thu 9/10
10:10 am-4:05 pm
1 stop5h 55m
$271
GreenvilleNorfolk
GSP - ORF
GSPORF
Greenville
Thu 11/5
8:15 am-11:35 am
1 stop3h 20m
Norfolk
Sun 11/8
6:15 am-10:10 am
1 stop3h 55m
$306
GreenvilleNorfolk
GSP - ORF
GSPORF
Greenville
Sat 7/25
6:55 am-3:15 pm
1 stop8h 20m
Norfolk
Wed 8/5
12:15 pm-8:55 pm
2 stops8h 40m
$321
GreenvilleNorfolk
GSP - ORF
GSPORF
Greenville
Tue 10/6
6:20 am-12:15 pm
1 stop5h 55m
Norfolk
Wed 10/7
6:00 am-10:45 am
1 stop4h 45m
$335
GreenvilleNorfolk
GSP - ORF
GSPORF
Greenville
Tue 8/11
7:47 pm-11:43 pm
1 stop3h 56m
Norfolk
Wed 8/12
6:10 pm-11:11 pm
1 stop5h 01m
$343
GreenvilleNorfolk
GSP - ORF
GSPORF
Greenville
Fri 8/14
1:05 pm-9:35 pm
2 stops8h 30m
Norfolk
Sat 8/15
6:25 am-2:55 pm
2 stops8h 30m
$343
GreenvilleNorfolk
GSP - ORF
GSPORF
Greenville
Mon 8/10
7:40 pm-11:44 pm
1 stop4h 04m
Norfolk
Wed 8/12
6:00 am-10:37 am
1 stop4h 37m
$351
Cheapest one-way
GreenvilleNorfolk
GSP - ORF
GSPORF
Greenville
Mon 8/10
4:57 pm-5:32 pm
2 stops24h 35m
$126
GreenvilleNorfolk
GSP - ORF
GSPORF
Greenville
Mon 8/10
8:13 pm-5:32 pm
3 stops21h 19m
$134
Showing 1-10 of 14 resultsSorted 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 June 27, 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.
Comfort
7.2
Boarding
7.5
Overall
7.1
Crew
7.9
Entertainment
6.8
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Comfort
7.2
Boarding
7.5
Overall
7.1
Crew
7.9
Entertainment
6.8
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
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
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Greenville and Chesapeake flights
Browse other Greenville and Chesapeake flight options. Last updated on June 27, 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 June 27, 2026.
Popular flight searches
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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 June 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$239 | Average$394 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$271 | Average$346 | FlexibilityNo cancel fee | On-timeN/A |