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Chesapeake

$320+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — RIC
nov. 29 — déc. 61
sam. 11/29
sam. 12/6
1 adult, Economy
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Find flight deals from Gulfport to Chesapeake

Cheapest flights from Gulfport to Chesapeake
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 octobre 30, 2025.

This United Airlines deal was found by Cheapflights users on 10/28. 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.
jeu. 11/131:57 pmGPT - ORF
2 stops8h 41mUnited Airlines
lun. 11/176:07 amORF - GPT
1 stop6h 10mUnited Airlines
Deal found 10/28$320
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
ven. 11/216:51 pmGPT - ORF
1 stop26h 12mMultiple Airlines
dim. 11/232:10 pmORF - GPT
1 stop6h 05mMultiple Airlines
Deal found 10/30$337
This Delta deal was found by Cheapflights users on 10/28. 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.
mar. 12/96:00 amGPT - ORF
1 stop4h 32mDelta
ven. 12/125:15 amORF - GPT
1 stop5h 35mDelta
Deal found 10/28$347
This American Airlines deal was found by Cheapflights users on 10/28. 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.
mar. 12/96:36 amGPT - ORF
2 stops12h 05mAmerican Airlines
ven. 12/1210:39 amORF - GPT
1 stop7h 23mAmerican Airlines
Deal found 10/28$352
This United Airlines deal was found by Cheapflights users on 10/28. 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.
ven. 10/311:57 pmGPT - ORF
1 stop7h 33mUnited Airlines
dim. 11/25:07 amORF - GPT
1 stop6h 10mUnited Airlines
Deal found 10/28$369
This Delta deal was found by Cheapflights users on 10/28. 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.
ven. 11/146:03 pmGPT - ORF
1 stop5h 10mDelta
lun. 11/175:15 amORF - GPT
1 stop5h 34mDelta
Deal found 10/28$419
This American Airlines deal was found by Cheapflights users on 10/28. 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.
ven. 11/145:26 pmGPT - ORF
1 stop4h 51mAmerican Airlines
lun. 11/175:55 amORF - GPT
2 stops8h 25mAmerican Airlines
Deal found 10/28$424

Cheap flight deals from Gulfport to Chesapeake

Keep the following information in mind while searching for Gulfport to Chesapeake flight deals. Data was last updated octobre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$337
(Delta)

Popular in

December

Cheapest in

May

Average price

$360
Provider with most accurate pricing for Gulfport Biloxi Regional-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Gulfport Biloxi Regional-Norfolk flights.
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From Gulfport Biloxi Regional to Chesapeake
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 octobre 30, 2025.
Use the filters below to find and compare flights from Gulfport to Chesapeake that are best for you.

Fly from

Gulfport

Fly to

Chesapeake

Route

Depart

Return

Price

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

jeu. 11/13

1:57 pm-11:38 pm

2 stops8h 41m

Norfolk

lun. 11/17

6:07 am-11:17 am

1 stop6h 10m

$320

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

sam. 2/21

3:00 pm-8:05 pm

1 stop4h 05m

Norfolk

mar. 2/24

5:30 am-9:41 am

1 stop5h 11m

$337

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

ven. 11/21

6:51 pm-10:03 pm

1 stop26h 12m

Norfolk

dim. 11/23

2:10 pm-7:15 pm

1 stop6h 05m

$337

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

sam. 2/21

6:00 am-11:32 am

1 stop4h 32m

Norfolk

mer. 2/25

5:30 am-9:41 am

1 stop5h 11m

$337

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

mar. 12/9

6:36 am-1:40 pm

1 stop6h 04m

Norfolk

ven. 12/12

10:39 am-5:02 pm

1 stop7h 23m

$347

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

sam. 2/21

1:58 pm-10:28 pm

1 stop7h 30m

Norfolk

mar. 2/24

6:10 am-1:20 pm

2 stops8h 10m

$368

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

sam. 2/21

4:39 pm-11:58 pm

1 stop6h 19m

Norfolk

mer. 2/25

1:40 pm-11:49 pm

2 stops11h 09m

$412

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

ven. 11/14

6:03 pm-12:13 am

1 stop5h 10m

Norfolk

lun. 11/17

5:15 am-9:49 am

1 stop5h 34m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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.
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

What is the cheapest month to book a flight from Gulfport to Chesapeake?

Currently, June is the cheapest month in which you can book a flight from Gulfport to Chesapeake (average of $69). Flying from Gulfport to Chesapeake in May is currently the most expensive (average of $178). 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.

What is the cheapest time of day to fly from GPT to C6E?

Find hourly flight availability from Gulfport to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octobre 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Gulfport to Chesapeake at noon. If you’re flexible enough to do this you can expect to save up to 37% on your trip compared to booking a flight in the morning.

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 octobre 30, 2025.
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.
Delta
7.9
Good
7,998 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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.

  • What airport do you fly from for flights from Gulfport to Chesapeake?

    For a flight from Gulfport to Chesapeake, you will be flying from Biloxi Regional. Gulfport Biloxi Regional (GPT) is just 3.1 mi from the center of the city. Biloxi Regional is the only Gulfport airport and it handles 0 outbound flights to Chesapeake per day. 2 airlines have flights to Chesapeake from Gulfport Biloxi Regional on a regular basis.

  • How long is the flight from Gulfport to Chesapeake?

    Airlines like United Airlines and Delta fly from Gulfport to Chesapeake in about 4h 05m. The time it takes to get you to your destination can typically vary by up to 4h 36m. Airlines will cover a distance of 864 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Gulfport to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Gulfport to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Gulfport to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Gulfport to Chesapeake.

  • Can I find deals for business class flights from Gulfport to Chesapeake?

    Yes. Cheapflights offers flight deals from Gulfport to Chesapeake by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Gulfport to Chesapeake?

    Currently, June is the cheapest month in which you can book a flight from Gulfport to Chesapeake (average of $69). Flying from Gulfport to Chesapeake in May is currently the most expensive (average of $178). 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.

See more FAQs

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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.
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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 octobre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$344FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$342FlexibilityNo cancel feeOn-timeN/A

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