$276+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — RIC
Jul 23 — Jul 301
Round-trip
1 adult, Economy
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Find cheap flights from Gulfport 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
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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 Gulfport to Chesapeake
Cheapest
Best
Last-minute
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 June 23, 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 June 23, 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.
Sun 7/127:25 pm
GPT
- ORF
2 stops38h 50m
Multiple Airlines
Sun 7/196:00 am
ORF
- GPT
1 stop26h 41m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$386
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/51:54 pm
GPT
- ORF
2 stops8h 37m
United Airlines
Tue 12/86:00 am
ORF
- GPT
2 stops11h 02m
United Airlines
Deal found 6/22![United Airlines logo]()
$399
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.
Sun 7/127:25 pm
GPT
- ORF
1 stop25h 16m
Breeze Airways
Sun 7/196:00 am
ORF
- GPT
1 stop26h 41m
Breeze Airways
Deal found 6/22![Breeze Airways logo]()
$408
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:35 pm
GPT
- ORF
1 stop4h 06m
American Airlines
Sun 7/268:20 pm
ORF
- GPT
1 stop4h 36m
American Airlines
Deal found 6/23![American Airlines logo]()
$432
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.
Mon 7/1310:06 am
GPT
- ORF
1 stop4h 44m
Delta
Mon 7/206:17 pm
ORF
- GPT
1 stop4h 57m
Delta
Deal found 6/22![Delta logo]()
$467
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/810:36 am
GPT
- ORF
1 stop6h 13m
American Airlines
Sun 7/128:20 pm
ORF
- GPT
1 stop4h 36m
American Airlines
Deal found 6/23![American Airlines logo]()
$501
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.
Tue 6/231:53 pm
GPT
- ORF
1 stop6h 49m
Delta
Sun 6/286:20 am
ORF
- GPT
1 stop4h 01m
Delta
Deal found 6/22![Delta logo]()
$540
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 June 23, 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 June 23, 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.
Sun 7/127:25 pm
GPT
- ORF
2 stops38h 50m
Multiple Airlines
Sun 7/196:00 am
ORF
- GPT
1 stop26h 41m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$395
This United Airlines deal was found by Cheapflights users on 6/21. 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 12/51:54 pm
GPT
- ORF
2 stops8h 37m
United Airlines
Tue 12/86:00 am
ORF
- GPT
2 stops11h 02m
United Airlines
Deal found 6/21![United Airlines logo]()
$399
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2210:06 am
GPT
- ORF
1 stop6h 06m
Delta
Sun 7/266:20 am
ORF
- GPT
1 stop3h 59m
Delta
Deal found 6/23![Delta logo]()
$432
Last-minute flights from Gulfport to ChesapeakeDiscover last-minute flight deals from Gulfport to Chesapeake. Data last updated June 23, 2026 and is based on user searches.
Discover last-minute flight deals from Gulfport to Chesapeake. Data last updated June 23, 2026 and is based on user searches.
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.
Tue 6/231:53 pm
GPT
- ORF
1 stop6h 49m
Delta
Sun 6/286:20 am
ORF
- GPT
1 stop4h 01m
Delta
Deal found 6/22![Delta logo]()
$540
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 6/255:56 pm
GPT
- ORF
1 stop5h 49m
Delta
Sun 6/286:22 pm
ORF
- GPT
1 stop4h 55m
Delta
Deal found 6/22![Delta logo]()
$605
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/810:36 am
GPT
- ORF
1 stop6h 13m
American Airlines
Sun 7/128:20 pm
ORF
- GPT
1 stop4h 36m
American Airlines
Deal found 6/23![American Airlines logo]()
$501
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.
Sun 7/127:25 pm
GPT
- ORF
2 stops38h 50m
Multiple Airlines
Sun 7/196:00 am
ORF
- GPT
1 stop26h 41m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$386
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.
Sun 7/127:25 pm
GPT
- ORF
1 stop25h 16m
Breeze Airways
Sun 7/196:00 am
ORF
- GPT
1 stop26h 41m
Breeze Airways
Deal found 6/22![Breeze Airways logo]()
$408
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.
Mon 7/1310:06 am
GPT
- ORF
1 stop4h 44m
Delta
Mon 7/206:17 pm
ORF
- GPT
1 stop4h 57m
Delta
Deal found 6/22![Delta logo]()
$467
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.
Mon 7/137:04 am
GPT
- ORF
2 stops8h 48m
American Airlines
Mon 7/206:24 pm
ORF
- GPT
1 stop6h 32m
American Airlines
Deal found 6/22![American Airlines logo]()
$661
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:35 pm
GPT
- ORF
1 stop4h 06m
American Airlines
Sun 7/268:20 pm
ORF
- GPT
1 stop4h 36m
American Airlines
Deal found 6/23![American Airlines logo]()
$432
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 June 23, 2026.
Search for one-way flight options from Gulfport to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/287:50 pm
GPT
- ORF
1 stop23h 50m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$276
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/310:06 am
GPT
- ORF
1 stop6h 11m
Delta
Deal found 6/23![Delta logo]()
$280
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/287:50 pm
GPT
- ORF
2 stops36h 30m
Breeze Airways
Deal found 6/23![Breeze Airways logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 6/295:31 pm
GPT
- ORF
1 stop18h 59m
Breeze Airways
Deal found 6/18![Breeze Airways logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 6/295:31 pm
GPT
- ORF
3 stops50h 09m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/37:04 am
GPT
- ORF
2 stops8h 50m
American Airlines
Deal found 6/19![American Airlines logo]()
$393
This KAYAK deal was found by Cheapflights users on 6/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:31 pm
GPT
- ORF
3 stops23h 55m
Breeze Airways
Deal found 6/19![Breeze Airways logo]()
$401
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 June 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $395 (Kiwi.com) |
One-way from | $276 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $446 |
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 June 23, 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 - ORF
GPTORF
Gulfport Biloxi Regional
Sun 7/12
7:25 pm-11:15 am
2 stops38h 50m
Norfolk
Sun 7/19
6:00 am-7:41 am
1 stop26h 41m
$395
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Sat 12/5
1:54 pm-11:31 pm
2 stops8h 37m
Norfolk
Tue 12/8
6:00 am-4:02 pm
2 stops11h 02m
$399
Quickest round-trip
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Wed 7/22
10:06 am-5:12 pm
1 stop6h 06m
Norfolk
Sun 7/26
6:20 am-9:19 am
1 stop3h 59m
$432
Cheapest one-way
Quickest one-way
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Fri 7/3
10:06 am-5:17 pm
1 stop6h 11m
$280
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Mon 6/29
5:31 pm-8:40 pm
3 stops50h 09m
$353
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Fri 7/3
7:04 am-4:54 pm
2 stops8h 50m
$393
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Fri 7/3
5:31 pm-6:26 pm
3 stops23h 55m
$401
Sorted 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 June 23, 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.
Entertainment
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Overall
7.8
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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Gulfport to Chesapeake by cabin class
Find flights from Gulfport to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Gulfport and Chesapeake flights
Browse other Gulfport and Chesapeake flight options. Last updated on June 23, 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 June 23, 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 June 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$374 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$263 | Average$433 | FlexibilityNo cancel fee | On-time71% |