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Chesapeake

$232+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — RIC
Mar 8 — Mar 151
Sun 3/8
Sun 3/15
1 adult, Economy
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Cheap 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 February 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/197:20 pm
GPT
-
ORF
1 stop18h 13m
Multiple Airlines
Wed 2/257:31 pm
ORF
-
GPT
2 stops24h 09m
Multiple Airlines
Deal found 2/4$232
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 2/276:54 pm
GPT
-
ORF
1 stop25h 42m
Multiple Airlines
Sat 3/78:44 pm
ORF
-
GPT
2 stops36h 16m
Multiple Airlines
Deal found 2/5$246
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/197:20 pm
GPT
-
ORF
1 stop18h 13m
Multiple Airlines
Sun 2/221:44 pm
ORF
-
GPT
1 stop5h 56m
Multiple Airlines
Deal found 2/4$251
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/236:54 pm
GPT
-
ORF
1 stop17h 37m
Multiple Airlines
Wed 2/257:31 pm
ORF
-
GPT
2 stops24h 09m
Multiple Airlines
Deal found 2/4$264
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/197:20 pm
GPT
-
ORF
1 stop18h 13m
Multiple Airlines
Thu 2/266:45 am
ORF
-
GPT
1 stop12h 55m
Multiple Airlines
Deal found 2/4$268
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/206:54 pm
GPT
-
ORF
2 stops23h 55m
Multiple Airlines
Sun 2/221:44 pm
ORF
-
GPT
1 stop5h 56m
Multiple Airlines
Deal found 2/4$273
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/206:54 pm
GPT
-
ORF
1 stop25h 42m
Multiple Airlines
Wed 2/257:31 pm
ORF
-
GPT
2 stops24h 09m
Multiple Airlines
Deal found 2/4$286
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 2/236:54 pm
GPT
-
ORF
1 stop17h 37m
Multiple Airlines
Thu 2/266:45 am
ORF
-
GPT
1 stop12h 55m
Multiple Airlines
Deal found 2/5$288
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/206:54 pm
GPT
-
ORF
2 stops23h 55m
Multiple Airlines
Thu 2/266:45 am
ORF
-
GPT
1 stop12h 55m
Multiple Airlines
Deal found 2/4$289

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 February 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$232
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$293
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.
Search Deals
From Gulfport Biloxi Regional to Chesapeake
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 6, 2026.
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

Fri 2/27

6:54 pm-9:36 pm

1 stop25h 42m

Norfolk

Sat 3/7

8:44 pm-8:00 am

2 stops36h 16m

$246

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Mon 2/23

6:54 pm-6:26 pm

2 stops22h 32m

Norfolk

Thu 2/26

6:45 am-6:40 pm

1 stop12h 55m

$273

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Thu 2/19

2:54 pm-8:28 pm

1 stop4h 34m

Norfolk

Mon 2/23

6:14 pm-9:54 pm

1 stop4h 40m

$377

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Fri 2/20

4:29 pm-9:36 pm

1 stop4h 07m

Norfolk

Tue 2/24

5:18 pm-11:49 pm

1 stop7h 31m

$377

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Fri 2/20

2:54 pm-10:23 pm

1 stop6h 29m

Norfolk

Sat 2/21

6:20 pm-9:54 pm

1 stop4h 34m

$377

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Sat 2/21

6:00 am-11:08 am

1 stop4h 08m

Norfolk

Sat 2/21

6:20 pm-9:54 pm

1 stop4h 34m

$377

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Thu 2/19

10:11 am-5:07 pm

1 stop5h 56m

Norfolk

Sat 2/21

5:25 am-9:40 am

1 stop5h 15m

$377

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Mon 2/23

6:00 pm-12:14 am

1 stop5h 14m

Norfolk

Wed 2/25

6:20 pm-9:54 pm

1 stop4h 34m

$377

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Fri 2/20

6:00 am-11:30 am

1 stop4h 30m

Norfolk

Wed 2/25

6:20 pm-9:54 pm

1 stop4h 34m

$377

GulfportNorfolk

GPT - ORF

GPTORF

Gulfport Biloxi Regional

Thu 2/12

7:20 pm-8:00 am

3 stops35h 40m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

Showing 1-10 of 11 results
1
2

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, February is the cheapest month in which you can book a flight from Gulfport to Chesapeake (average of $66). 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.

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 February 6, 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.
Delta
7.9
Good
8,151 reviews

Overall

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.9

Boarding

8.1

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
8,151 reviews
Delta
7.9
Good
8,151 reviews

Overall

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.9

Boarding

8.1

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
11,237 reviews
Delta
7.9
Good
8,151 reviews

Overall

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.9

Boarding

8.1

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 Delta fly from Gulfport to Chesapeake in about 4h 34m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 864 mi.

  • 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, February is the cheapest month in which you can book a flight from Gulfport to Chesapeake (average of $66). 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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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 February 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$358FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$253Average$389FlexibilityNo cancel feeOn-time71%

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