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Chesapeake

$86+ Cheap flights from Pensacola (PNS) 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.
PNS — RIC
Feb 10 — Feb 171
Tue 2/10
Tue 2/17
1 adult, Economy
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Cheap flight deals from Pensacola to Chesapeake

Keep the following information in mind while searching for Pensacola to Chesapeake flight deals. Data was last updated January 11, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$174
(Kiwi.com)

One-way from

$86
(Trip.com)

Popular in

January

Cheapest in

August

Average price

$467
Provider with most accurate pricing for Pensacola-Norfolk flight deals.
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Provider most trusted by Cheapflights users for Pensacola-Norfolk flights.
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From Pensacola to Chesapeake
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One-way flight from Pensacola to Chesapeake
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Highest demand for flights based on searches. 17% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Pensacola to Chesapeake

Cheapest flights from Pensacola to Chesapeake
Explore the most affordable flight options available from Pensacola to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/8. 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 2/206:37 pmPNS - ORF
1 stop15h 58mMultiple Airlines
Mon 2/238:49 amORF - PNS
1 stop9h 53mMultiple Airlines
Deal found 1/8$174
This Kiwi.com deal was found by Cheapflights users on 1/10. 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 2/95:33 pmPNS - ORF
1 stop17h 32mMultiple Airlines
Mon 2/167:31 pmORF - PNS
1 stop21h 23mMultiple Airlines
Deal found 1/10$175
This Expedia deal was found by Cheapflights users on 1/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/291:18 pmPNS - ORF
1 stop8h 08mMultiple Airlines
Sun 2/16:45 amORF - PNS
1 stop10h 52mMultiple Airlines
Deal found 1/8$178
This Kiwi.com deal was found by Cheapflights users on 1/9. 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.
Wed 2/186:37 pmPNS - ORF
1 stop22h 51mMultiple Airlines
Wed 2/257:31 pmORF - PNS
1 stop21h 23mMultiple Airlines
Deal found 1/9$183
This Kiwi.com deal was found by Cheapflights users on 1/8. 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.
Tue 2/35:33 pmPNS - ORF
1 stop22h 47mMultiple Airlines
Sun 2/89:37 pmORF - PNS
1 stop20h 00mMultiple Airlines
Deal found 1/8$184
This Kiwi.com deal was found by Cheapflights users on 1/9. 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 2/196:37 pmPNS - ORF
1 stop18h 56mMultiple Airlines
Wed 2/257:31 pmORF - PNS
1 stop21h 23mMultiple Airlines
Deal found 1/9$185
This Mytrip deal was found by Cheapflights users on 1/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 amPNS - ORF
1 stop9h 53mSpirit Airlines
Mon 4/205:48 pmORF - PNS
1 stop4h 33mSpirit Airlines
Deal found 1/10$189
This Kiwi.com deal was found by Cheapflights users on 1/9. 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 2/196:37 pmPNS - ORF
1 stop18h 56mMultiple Airlines
Sun 2/226:45 amORF - PNS
1 stop11h 57mMultiple Airlines
Deal found 1/9$190
This Kiwi.com deal was found by Cheapflights users on 1/9. 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 2/126:37 pmPNS - ORF
1 stop18h 56mMultiple Airlines
Sun 2/157:31 pmORF - PNS
1 stop21h 23mMultiple Airlines
Deal found 1/9$193

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pensacola 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 January 11, 2026.
Use the filters below to find and compare flights from Pensacola to Chesapeake that are best for you.

Fly from

Pensacola

Fly to

Chesapeake

Route

Depart

Return

Price

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 2/18

6:37 pm-6:28 pm

1 stop22h 51m

Norfolk

Wed 2/25

7:31 pm-3:54 pm

1 stop21h 23m

$183

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 2/19

6:37 pm-2:33 pm

1 stop18h 56m

Norfolk

Sun 2/22

6:45 am-5:42 pm

1 stop11h 57m

$183

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Tue 2/3

5:33 pm-5:20 pm

1 stop22h 47m

Norfolk

Sun 2/8

9:37 pm-4:37 pm

1 stop20h 00m

$184

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Tue 4/7

2:24 pm-7:31 pm

1 stop28h 07m

Norfolk

Tue 4/14

8:29 pm-12:52 pm

1 stop17h 23m

$193

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Mon 2/9

5:33 pm-12:05 pm

1 stop17h 32m

Norfolk

Mon 2/16

1:42 pm-3:54 pm

2 stops27h 12m

$201

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sun 2/8

4:03 pm-6:38 pm

1 stop25h 35m

Norfolk

Sun 2/15

7:31 pm-3:54 pm

1 stop21h 23m

$210

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 2/13

5:20 pm-11:35 am

2 stops17h 15m

Norfolk

Mon 2/16

7:31 pm-3:54 pm

1 stop21h 23m

$217

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 1/21

5:33 pm-3:06 pm

1 stop20h 33m

Norfolk

Sat 1/31

6:45 am-4:37 pm

1 stop10h 52m

$224

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 1/22

1:18 pm-10:26 pm

1 stop8h 08m

Norfolk

Sun 1/25

9:37 pm-4:37 pm

1 stop20h 00m

$226

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 2/19

1:18 pm-10:26 pm

1 stop8h 08m

Norfolk

Mon 2/23

7:00 am-2:32 pm

1 stop8h 32m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

Showing 1-10 of 20 results
1
2

Best time to book a flight from Pensacola to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Pensacola 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 Pensacola to Chesapeake

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

Currently, September is the cheapest month in which you can book a flight from Pensacola to Chesapeake (average of $125). Flying from Pensacola to Chesapeake in December is currently the most expensive (average of $307). 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 January 11, 2026.
Read reviews from past customers who have flown Delta, American Airlines, and Spirit Airlines from Pensacola to Chesapeake. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,037 reviews

Food

7.2

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,037 reviews
Delta
7.9
Good
8,037 reviews

Food

7.2

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,100 reviews
Delta
7.9
Good
8,037 reviews

Food

7.2

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Spirit Airlines
6.3
Okay
8,300 reviews
Delta
7.9
Good
8,037 reviews

Food

7.2

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Pensacola 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 Pensacola to Chesapeake?

    Pensacola (PNS), located 4.0 mi from the city center, is the airport you fly out of when you book flights from Pensacola to Chesapeake. 3 airlines have flights from Pensacola to Chesapeake on a regular basis. Booking flights from Pensacola to Chesapeake should not be difficult; the airport handles an average of 0 outbound flights to Chesapeake per day.

  • How long is the flight from Pensacola to Chesapeake?

    There are many flights that can get you from Pensacola to Chesapeake in 28h 07m. Fly via Spirit Airlines to get the fastest option. The distance between Pensacola and Chesapeake is about 770 mi.

  • What are the cheapest airlines to fly from Pensacola to Chesapeake one-way?

    $60 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $104 and $118, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Pensacola 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 Pensacola to Chesapeake?

    Currently, September is the cheapest month in which you can book a flight from Pensacola to Chesapeake (average of $125). Flying from Pensacola to Chesapeake in December is currently the most expensive (average of $307). 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 3 airlines flying from Pensacola to Chesapeake

Discover the top 3 airlines that operate flights from Pensacola 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 January 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$109Average$285FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$176Average$407FlexibilityNo cancel feeOn-time71%
DeltaCheapest$194Average$362FlexibilityNo cancel feeOn-timeN/A

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