$381+ Cheap flights from Gulfport (GPT) to Chesapeake, VA
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/29. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — RIC
Oct 21 — Oct 281
Round-trip
1 adult, Economy
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Find cheap flights from Gulfport 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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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 September 21, 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 September 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/157:45 pm -
1 stop18h 19m
Sun 10/186:00 am -
1 stop14h 05m
Deal found 9/17![Breeze Airways logo]()
$402
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 10/212:00 pm -
2 stops10h 44m
Tue 10/66:00 am -
1 stop8h 25m
Deal found 9/17![United Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Wed 10/216:42 pm -
1 stop4h 15m
Mon 10/266:17 pm -
1 stop6h 42m
Deal found 9/20![American Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 9/17. 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 11/126:19 am -
1 stop5h 56m
Fri 11/136:16 pm -
1 stop6h 43m
Deal found 9/17![American Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 9/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/156:15 am -
1 stop6h 40m
Tue 12/2210:15 am -
1 stop7h 20m
Deal found 9/20![Delta logo]()
$432
This American Airlines deal was found by Cheapflights users on 9/17. 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 12/236:04 pm -
1 stop4h 55m
Fri 12/258:19 pm -
1 stop4h 38m
Deal found 9/17![American Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 9/17. 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 10/26:25 am -
1 stop4h 31m
Tue 10/65:25 pm -
1 stop5h 51m
Deal found 9/17![Delta logo]()
$514
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/172:00 pm -
1 stop7h 28m
Wed 10/216:20 am -
2 stops10h 52m
Deal found 9/16![United Airlines logo]()
$538
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 September 21, 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 September 21, 2026.
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 10/212:00 pm -
2 stops10h 44m
Tue 10/66:00 am -
1 stop8h 25m
Deal found 9/17![United Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 9/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/156:15 am -
1 stop6h 40m
Tue 12/2210:15 am -
1 stop7h 20m
Deal found 9/20![Delta logo]()
$432
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Wed 10/216:11 am -
2 stops7h 58m
Mon 10/267:59 pm -
1 stop5h 00m
Deal found 9/20![American Airlines logo]()
$571
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:00 pm -
1 stop7h 28m
Wed 10/216:20 am -
2 stops10h 52m
Deal found 9/20![United Airlines logo]()
$546
Last-minute flights from Gulfport to ChesapeakeDiscover last-minute flight deals from Gulfport to Chesapeake. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Gulfport to Chesapeake. Data last updated September 21, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 10/212:00 pm -
2 stops10h 44m
Tue 10/66:00 am -
1 stop8h 25m
Deal found 9/17![United Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 9/17. 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 10/26:25 am -
1 stop4h 31m
Tue 10/65:25 pm -
1 stop5h 51m
Deal found 9/17![Delta logo]()
$514
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/157:45 pm -
1 stop18h 19m
Sun 10/186:00 am -
1 stop14h 05m
Deal found 9/17![Breeze Airways logo]()
$402
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/172:00 pm -
1 stop7h 28m
Wed 10/216:20 am -
2 stops10h 52m
Deal found 9/16![United Airlines logo]()
$538
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Wed 10/216:42 pm -
1 stop4h 15m
Mon 10/266:17 pm -
1 stop6h 42m
Deal found 9/20![American Airlines logo]()
$416
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 September 21, 2026.
Search for one-way flight options from Gulfport to Chesapeake. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 11/293:53 pm -
1 stop23h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 9/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2910:06 am -
1 stop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Delta logo]()
$410
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:00 pm -
2 stops8h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![United Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 11/293:53 pm -
3 stops29h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Breeze Airways logo]()
$462
This Delta deal was found by Cheapflights users on 9/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:06 am -
1 stop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Delta logo]()
$473
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/282:00 pm -
2 stops8h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![United Airlines logo]()
$478
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:08 am -
3 stops15h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![United Airlines logo]()
$483
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 September 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $402 (Kiwi.com) |
One-way from | $381 (Kiwi.com) |
Popular in | January |
Cheapest in | February |
Average price | $454 |
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 7,457,451 searches. Data last updated September 21, 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 10/2
12:00 pm-11:44 pm
2 stops10h 44m
Norfolk
Tue 10/6
6:00 am-1:25 pm
1 stop8h 25m
$404
Quickest round-trip
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Tue 9/29
10:06 am-3:56 pm
1 stop4h 50m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$410
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Tue 9/29
2:00 pm-11:44 pm
2 stops8h 44m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$415
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Sun 11/29
3:53 pm-6:49 pm
2 stops25h 56m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$421
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Tue 12/15
6:15 am-1:55 pm
1 stop6h 40m
Norfolk
Tue 12/22
10:15 am-4:35 pm
1 stop7h 20m
$432
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Sun 11/29
3:53 pm-10:43 pm
3 stops29h 50m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$462
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Mon 9/28
10:06 am-3:56 pm
1 stop4h 50m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$473
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Mon 9/28
2:00 pm-11:48 pm
2 stops8h 48m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$478
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Sat 10/17
2:00 pm-10:28 pm
1 stop7h 28m
Norfolk
Wed 10/21
6:20 am-4:12 pm
2 stops10h 52m
$546
GulfportNorfolk
GPT Gulfport Biloxi Regional - ORF Norfolk
GPTORF
Gulfport Biloxi Regional
Wed 10/21
6:11 am-3:09 pm
2 stops7h 58m
Norfolk
Mon 10/26
7:59 pm-11:59 pm
1 stop5h 00m
$571
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
How much does it cost to fly round-trip from Gulfport to Chesapeake?
Airfare is below average for this route at the moment.
Gulfport to Chesapeake flights typically cost between $442 and $607 in October.The cheapest round-trip price found within the last 5 days was $402 on Breeze Airways (Oct 15-Oct 18).
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 September 21, 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.
Boarding
8.1
Food
7.2
Overall
7.8
Crew
8.5
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Food
7.2
Overall
7.8
Crew
8.5
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Food
7.2
Overall
7.8
Crew
8.5
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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 September 21, 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 September 21, 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 7,457,451 searches. Data last updated September 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$473 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$263 | Average$439 | FlexibilityNo cancel fee | On-time71% |