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Chesapeake

$122+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — RIC
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Gulfport to Chesapeake

Best flights from Gulfport to Chesapeake
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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 4/222:00 pmGPT - ORF
1 stop7h 18mUnited Airlines
Sat 4/256:00 amORF - GPT
2 stops11h 02mUnited Airlines
Deal found 12/17$326
This American Airlines deal was found by Cheapflights users on 12/17. 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 4/226:53 pmGPT - ORF
1 stop3h 39mAmerican Airlines
Sat 4/256:17 pmORF - GPT
1 stop4h 06mAmerican Airlines
Deal found 12/17$337
This Delta deal was found by Cheapflights users on 12/17. 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.
Sun 1/252:40 pmGPT - ORF
1 stop4h 50mDelta
Sun 2/110:15 amORF - GPT
1 stop4h 36mDelta
Deal found 12/17$407
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Thu 1/291:57 pmGPT - ORF
2 stops8h 33mUnited Airlines
Mon 2/26:30 amORF - GPT
2 stops10h 28mUnited Airlines
Deal found 12/16$384
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Sun 1/256:32 amGPT - ORF
2 stops11h 04mAmerican Airlines
Sun 2/16:00 amORF - GPT
2 stops8h 19mAmerican Airlines
Deal found 12/17$417

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$326
(United Airlines)

One-way from

$122
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$676
Provider with most accurate pricing for Gulfport Biloxi Regional-Norfolk flight deals.
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Provider most trusted by Cheapflights users for Gulfport Biloxi Regional-Norfolk flights.
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From Gulfport Biloxi Regional to Chesapeake
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One-way flight from Gulfport Biloxi Regional to Chesapeake
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in December 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 December 18, 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

Wed 4/22

2:00 pm-10:18 pm

1 stop7h 18m

Norfolk

Sat 4/25

6:00 am-4:02 pm

2 stops11h 02m

$326

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Wed 4/22

6:53 pm-11:32 pm

1 stop3h 39m

Norfolk

Sat 4/25

6:17 pm-9:23 pm

1 stop4h 06m

$337

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Thu 1/29

1:57 pm-11:30 pm

2 stops8h 33m

Norfolk

Mon 2/2

6:30 am-3:58 pm

2 stops10h 28m

$384

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Sun 1/25

2:40 pm-8:30 pm

1 stop4h 50m

Norfolk

Sun 2/1

10:15 am-1:51 pm

1 stop4h 36m

$407

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Sun 1/25

6:32 am-6:36 pm

2 stops11h 04m

Norfolk

Sun 2/1

6:00 am-1:19 pm

2 stops8h 19m

$417

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Mon 2/9

6:54 pm-6:38 pm

2 stops22h 44m

$131

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Sun 1/4

7:50 pm-1:09 pm

2 stops16h 19m

$199

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Wed 1/21

1:57 pm-10:30 pm

1 stop7h 33m

$475

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Wed 1/21

10:21 am-5:05 pm

1 stop5h 44m

$850

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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 December 18, 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.

How much does it cost to fly round-trip from Gulfport to Chesapeake?

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 December 18, 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
8,005 reviews

Food

7.3

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,005 reviews
Delta
7.9
Good
8,005 reviews

Food

7.3

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,054 reviews
Delta
7.9
Good
8,005 reviews

Food

7.3

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 American Airlines fly from Gulfport to Chesapeake in about 3h 39m. The time it takes to get you to your destination can typically vary by up to 3h 39m. 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.

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$379FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$353FlexibilityNo cancel feeOn-timeN/A

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