$196+ Cheap flights from Gulfport (GPT) 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — RIC
Sep 6 — Sep 131
Round-trip
1 adult, Economy
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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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Best
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One-way
Cheapest flights from Gulfport to ChesapeakeExplore the most affordable flight options available from Gulfport to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 7, 2026.
Explore the most affordable flight options available from Gulfport to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 10/87:45 pm -
1 stop20h 45m
Thu 10/1512:57 pm -
2 stops20h 54m
Deal found 8/5![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 8/215:31 pm -
1 stop26h 24m
Sun 8/237:00 am -
1 stop12h 45m
Deal found 8/3![Breeze Airways logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 8/215:31 pm -
2 stops17h 54m
Sun 8/237:00 am -
1 stop12h 45m
Deal found 8/3![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 9/45:31 pm -
2 stops17h 54m
Sun 9/67:40 am -
1 stop25h 01m
Deal found 8/4![Multiple Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 8/5. 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 8/277:40 am -
1 stop5h 22m
Tue 9/85:26 pm -
1 stop6h 04m
Deal found 8/5![American Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Fri 9/117:49 am -
1 stop6h 10m
Sun 9/136:15 pm -
1 stop6h 42m
Deal found 8/4![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/37:40 am -
1 stop6h 28m
Mon 9/145:21 pm -
1 stop6h 11m
Deal found 8/2![American Airlines logo]()
$451
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/241:42 pm -
1 stop4h 03m
Sun 9/278:09 pm -
1 stop4h 48m
Deal found 8/6![American Airlines logo]()
$454
Best flights from Gulfport to ChesapeakeDiscover carefully curated flight deals from Gulfport to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 7, 2026.
Discover carefully curated flight deals from Gulfport to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 8/215:31 pm -
1 stop26h 24m
Sun 8/237:00 am -
1 stop12h 45m
Deal found 8/3![Breeze Airways logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 8/215:31 pm -
2 stops17h 54m
Sun 8/237:00 am -
1 stop12h 45m
Deal found 8/5![Multiple Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 8/5. 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 8/277:40 am -
1 stop5h 22m
Tue 9/85:26 pm -
1 stop6h 04m
Deal found 8/5![American Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 8/6. 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.
Sat 10/246:26 am -
1 stop6h 42m
Sat 10/315:25 pm -
1 stop4h 21m
Deal found 8/6![Delta logo]()
$387
This United Airlines deal was found by Cheapflights users on 8/2. 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 8/202:00 pm -
2 stops8h 43m
Tue 8/256:10 am -
1 stop8h 14m
Deal found 8/2![United Airlines logo]()
$461
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/37:40 am -
1 stop6h 28m
Mon 9/145:21 pm -
1 stop6h 11m
Deal found 8/2![American Airlines logo]()
$451
This Delta deal was found by Cheapflights users on 8/4. 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 10/25:59 pm -
1 stop5h 39m
Sun 10/45:02 pm -
1 stop6h 06m
Deal found 8/4![Delta logo]()
$457
This United Airlines deal was found by Cheapflights users on 8/4. 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 9/124:59 pm -
2 stops20h 52m
Tue 9/156:10 am -
2 stops11h 02m
Deal found 8/4![United Airlines logo]()
$589
This United Airlines deal was found by Cheapflights users on 8/6. 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 10/314:55 pm -
2 stops29h 39m
Tue 11/36:00 am -
2 stops11h 08m
Deal found 8/6![United Airlines logo]()
$596
Last-minute flights from Gulfport to ChesapeakeDiscover last-minute flight deals from Gulfport to Chesapeake. Data last updated August 7, 2026 and is based on user searches.
Discover last-minute flight deals from Gulfport to Chesapeake. Data last updated August 7, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/2. 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 8/202:00 pm -
2 stops8h 43m
Tue 8/256:10 am -
1 stop8h 14m
Deal found 8/2![United Airlines logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 8/215:31 pm -
1 stop26h 24m
Sun 8/237:00 am -
1 stop12h 45m
Deal found 8/3![Breeze Airways logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 8/215:31 pm -
2 stops17h 54m
Sun 8/237:00 am -
1 stop12h 45m
Deal found 8/3![Multiple Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 8/5. 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 8/277:40 am -
1 stop5h 22m
Tue 9/85:26 pm -
1 stop6h 04m
Deal found 8/5![American Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/37:40 am -
1 stop6h 28m
Mon 9/145:21 pm -
1 stop6h 11m
Deal found 8/2![American Airlines logo]()
$451
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 9/45:31 pm -
2 stops17h 54m
Sun 9/67:40 am -
1 stop25h 01m
Deal found 8/4![Multiple Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Fri 9/117:49 am -
1 stop6h 10m
Sun 9/136:15 pm -
1 stop6h 42m
Deal found 8/4![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/241:42 pm -
1 stop4h 03m
Sun 9/278:09 pm -
1 stop4h 48m
Deal found 8/6![American Airlines logo]()
$454
One-way flights from Gulfport to ChesapeakeSearch for one-way flight options from Gulfport to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 7, 2026.
Search for one-way flight options from Gulfport to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 8/175:31 pm -
3 stops23h 01m
Deal found 8/2![Breeze Airways logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 8/175:31 pm -
2 stops17h 54m
Deal found 8/2![Multiple Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Sun 8/167:25 pm -
2 stops36h 55m
Deal found 8/6![Breeze Airways logo]()
$238
This Delta deal was found by Cheapflights users on 8/4. 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 8/186:00 pm -
1 stop6h 03m
Deal found 8/4![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 8/4. 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 8/187:08 am -
2 stops9h 19m
Deal found 8/4![United Airlines logo]()
$304
Find flight deals from Gulfport to Chesapeake
Keep the following information in mind while searching for Gulfport to Chesapeake flight deals. Data was last updated August 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (Kiwi.com) |
One-way from | $196 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $420 |
Cheapflights Fare Finder
Customize your flight search to find flights from Gulfport 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 7, 2026.
Use the filters below to find and compare flights from Gulfport to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Fri 8/21
5:31 pm-8:55 pm
1 stop26h 24m
Norfolk
Sun 8/23
7:00 am-6:45 pm
1 stop12h 45m
$309
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Fri 8/21
5:31 pm-12:25 pm
2 stops17h 54m
Norfolk
Sun 8/23
7:00 am-6:45 pm
1 stop12h 45m
$345
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Thu 8/27
7:40 am-2:02 pm
1 stop5h 22m
Norfolk
Tue 9/8
5:26 pm-10:30 pm
1 stop6h 04m
$387
Quickest round-trip
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Sat 10/24
6:26 am-2:08 pm
1 stop6h 42m
Norfolk
Sat 10/31
5:25 pm-8:46 pm
1 stop4h 21m
$387
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Thu 9/3
7:40 am-3:08 pm
1 stop6h 28m
Norfolk
Mon 9/14
5:21 pm-10:32 pm
1 stop6h 11m
$451
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Fri 10/2
5:59 pm-12:38 am
1 stop5h 39m
Norfolk
Sun 10/4
5:02 pm-10:08 pm
1 stop6h 06m
$457
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Thu 8/20
2:00 pm-11:43 pm
2 stops8h 43m
Norfolk
Tue 8/25
6:10 am-1:24 pm
1 stop8h 14m
$461
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Sat 9/12
4:59 pm-2:51 pm
2 stops20h 52m
Norfolk
Tue 9/15
6:10 am-4:12 pm
2 stops11h 02m
$589
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Sat 10/31
4:55 pm-11:34 pm
2 stops29h 39m
Norfolk
Tue 11/3
6:00 am-4:08 pm
2 stops11h 08m
$596
Cheapest one-way
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Mon 8/17
5:31 pm-5:32 pm
3 stops23h 01m
$196
Showing 1-10 of 16 resultsSorted by cheapest first
Best time to book a flight from Gulfport to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Gulfport with our price prediction graph.
GPT-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 Gulfport to Chesapeake
GPT-C6E
GPT-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 7, 2026.
Read through reviews of airlines operating flights from Gulfport to Chesapeake, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Comfort
7.8
Food
7.2
Entertainment
7.8
Overall
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Comfort
7.8
Food
7.2
Entertainment
7.8
Overall
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Comfort
7.8
Food
7.2
Entertainment
7.8
Overall
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Gulfport 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 Gulfport 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.
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Gulfport and Chesapeake flights
Browse other Gulfport and Chesapeake flight options. Last updated on August 7, 2026.
Other flights from Gulfport
Browse through other flights departing from Gulfport. Flights are based on user searches made on Cheapflights and were last updated on August 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Gulfport to Chesapeake flights
Consider these flights traveling from Gulfport to Chesapeake.
Top 2 airlines flying from Gulfport to Chesapeake
Discover the top 2 airlines that operate flights from Gulfport 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 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$452 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$263 | Average$436 | FlexibilityNo cancel fee | On-time71% |