$111+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — RIC
Apr 23 — Apr 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 March 24, 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 March 24, 2026.
This American Airlines deal was found by Cheapflights users on 3/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:09 pm
GPT
- ORF
1 stop4h 50m
American Airlines
Tue 5/55:13 pm
ORF
- GPT
1 stop7h 13m
American Airlines
Deal found 3/21![American Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 3/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:09 pm
GPT
- ORF
1 stop4h 50m
American Airlines
Tue 5/56:00 am
ORF
- GPT
1 stop7h 01m
American Airlines
Deal found 3/21![American Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/197:20 pm
GPT
- ORF
1 stop25h 27m
Multiple Airlines
Wed 3/258:41 pm
ORF
- GPT
2 stops37h 19m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$425
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 4/36:54 pm
GPT
- ORF
1 stop25h 42m
Multiple Airlines
Sun 4/59:04 am
ORF
- GPT
1 stop10h 36m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 3/22. 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.
Wed 8/262:00 pm
GPT
- ORF
2 stops8h 43m
United Airlines
Sat 8/296:30 am
ORF
- GPT
2 stops10h 32m
United Airlines
Deal found 3/22![United Airlines logo]()
$443
This American Airlines deal was found by Cheapflights users on 3/19. 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.
Thu 4/236:00 am
GPT
- ORF
1 stop5h 42m
American Airlines
Sun 5/311:02 am
ORF
- GPT
1 stop7h 31m
American Airlines
Deal found 3/19![American Airlines logo]()
$447
This American Airlines deal was found by Cheapflights users on 3/19. 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 4/246:09 pm
GPT
- ORF
1 stop4h 50m
American Airlines
Mon 5/44:51 pm
ORF
- GPT
2 stops8h 07m
American Airlines
Deal found 3/19![American Airlines logo]()
$452
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 March 24, 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 March 24, 2026.
This United Airlines deal was found by Cheapflights users on 3/22. 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.
Wed 8/262:00 pm
GPT
- ORF
2 stops8h 43m
United Airlines
Sat 8/296:30 am
ORF
- GPT
2 stops10h 32m
United Airlines
Deal found 3/22![United Airlines logo]()
$443
This American Airlines deal was found by Cheapflights users on 3/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:09 pm
GPT
- ORF
1 stop4h 50m
American Airlines
Mon 5/41:32 pm
ORF
- GPT
1 stop5h 01m
American Airlines
Deal found 3/21![American Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 3/22. 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.
Sun 5/316:02 pm
GPT
- ORF
1 stop5h 46m
Delta
Sat 6/136:00 am
ORF
- GPT
1 stop4h 21m
Delta
Deal found 3/22![Delta logo]()
$478
This American Airlines deal was found by Cheapflights users on 3/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:42 pm
GPT
- ORF
2 stops9h 24m
American Airlines
Tue 5/56:00 am
ORF
- GPT
2 stops7h 01m
American Airlines
Deal found 3/21![American Airlines logo]()
$463
This United Airlines deal was found by Cheapflights users on 3/21. 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.
Thu 4/232:05 pm
GPT
- ORF
2 stops8h 27m
United Airlines
Mon 5/46:15 am
ORF
- GPT
2 stops10h 58m
United Airlines
Deal found 3/21![United Airlines logo]()
$478
This United Airlines deal was found by Cheapflights users on 3/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:05 pm
GPT
- ORF
2 stops8h 27m
United Airlines
Sun 5/36:15 am
ORF
- GPT
2 stops10h 58m
United Airlines
Deal found 3/19![United Airlines logo]()
$542
Last-minute flights from Gulfport to ChesapeakeDiscover last-minute flight deals from Gulfport to Chesapeake. Data last updated March 24, 2026 and is based on user searches.
Discover last-minute flight deals from Gulfport to Chesapeake. Data last updated March 24, 2026 and is based on user searches.
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 4/36:54 pm
GPT
- ORF
1 stop25h 42m
Multiple Airlines
Sun 4/59:04 am
ORF
- GPT
1 stop10h 36m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 3/20. 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 4/46:00 am
GPT
- ORF
2 stops10h 30m
American Airlines
Wed 4/82:08 pm
ORF
- GPT
2 stops10h 50m
American Airlines
Deal found 3/20![American Airlines logo]()
$472
This American Airlines deal was found by Cheapflights users on 3/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:09 pm
GPT
- ORF
1 stop4h 50m
American Airlines
Tue 5/55:13 pm
ORF
- GPT
1 stop7h 13m
American Airlines
Deal found 3/21![American Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 3/19. 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.
Thu 4/236:00 am
GPT
- ORF
1 stop5h 42m
American Airlines
Sun 5/311:02 am
ORF
- GPT
1 stop7h 31m
American Airlines
Deal found 3/19![American Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 3/21. 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.
Thu 4/232:05 pm
GPT
- ORF
2 stops8h 27m
United Airlines
Mon 5/46:15 am
ORF
- GPT
2 stops10h 58m
United Airlines
Deal found 3/21![United Airlines logo]()
$478
This American Airlines deal was found by Cheapflights users on 3/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:09 pm
GPT
- ORF
1 stop4h 50m
American Airlines
Tue 5/56:00 am
ORF
- GPT
1 stop7h 01m
American Airlines
Deal found 3/21![American Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 3/19. 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 4/246:09 pm
GPT
- ORF
1 stop4h 50m
American Airlines
Mon 5/44:51 pm
ORF
- GPT
2 stops8h 07m
American Airlines
Deal found 3/19![American Airlines logo]()
$452
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 March 24, 2026.
Search for one-way flight options from Gulfport to Chesapeake. Find affordable one-way fares based on user searches. Data last updated March 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:50 pm
GPT
- ORF
1 stop24h 11m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/57:20 pm
GPT
- ORF
1 stop25h 27m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:50 pm
GPT
- ORF
3 stops25h 58m
Breeze Airways
Deal found 3/21![Breeze Airways logo]()
$236
This Delta deal was found by Cheapflights users on 3/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:53 pm
GPT
- ORF
1 stop4h 06m
Delta
Deal found 3/21![Delta logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/57:20 pm
GPT
- ORF
3 stops59h 40m
Breeze Airways
Deal found 3/20![Breeze Airways logo]()
$344
This American Airlines deal was found by Cheapflights users on 3/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1010:39 am
GPT
- ORF
2 stops10h 14m
American Airlines
Deal found 3/21![American Airlines logo]()
$408
This United Airlines deal was found by Cheapflights users on 3/21. 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.
Wed 6/102:00 pm
GPT
- ORF
3 stops30h 42m
United Airlines
Deal found 3/21![United Airlines logo]()
$648
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 March 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $377 (American Airlines) |
One-way from | $111 (Kiwi.com) |
Popular in | January |
Cheapest in | May |
Average price | $395 |
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 March 24, 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
Wed 8/26
2:00 pm-11:43 pm
2 stops8h 43m
Norfolk
Sat 8/29
6:30 am-4:02 pm
2 stops10h 32m
$443
Quickest round-trip
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Fri 4/24
6:09 pm-11:59 pm
1 stop4h 50m
Norfolk
Mon 5/4
1:32 pm-5:33 pm
1 stop5h 01m
$447
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Wed 4/22
12:42 pm-11:06 pm
2 stops9h 24m
Norfolk
Tue 5/5
6:00 am-12:01 pm
2 stops7h 01m
$463
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Sun 5/31
6:02 pm-12:48 am
1 stop5h 46m
Norfolk
Sat 6/13
6:00 am-9:21 am
1 stop4h 21m
$478
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Thu 4/23
2:05 pm-11:32 pm
2 stops8h 27m
Norfolk
Mon 5/4
6:15 am-4:13 pm
2 stops10h 58m
$478
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Thu 4/23
2:05 pm-11:32 pm
2 stops8h 27m
Norfolk
Sun 5/3
6:15 am-4:13 pm
2 stops10h 58m
$542
Cheapest one-way
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Thu 6/11
7:50 pm-9:01 pm
1 stop24h 11m
$111
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Sun 4/5
7:20 pm-10:38 am
2 stops14h 18m
$262
Quickest one-way
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Wed 6/10
1:53 pm-6:59 pm
1 stop4h 06m
$267
GulfportNorfolk
GPT - ORF
GPTORF
Gulfport Biloxi Regional
Sun 4/5
7:20 pm-8:00 am
3 stops59h 40m
$344
Showing 1-10 of 12 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
What is the cheapest month to book a flight from Gulfport to Chesapeake?
Currently, February is the cheapest month in which you can book a flight from Gulfport to Chesapeake (average of $63). Flying from Gulfport to Chesapeake in May is currently the most expensive (average of $186). 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.
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 24, 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.
Comfort
7.9
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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 March 24, 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 March 24, 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 March 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$253 | Average$377 | FlexibilityNo cancel fee | On-time71% |