Chesapeake

$81+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — RIC
Jun 7 — Jun 141
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Cheap 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 May 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/6. 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 10/158:18 am
PNS
-
ORF
1 stop5h 46m
Breeze Airways
Wed 10/218:00 am
ORF
-
PNS
1 stop5h 45m
Breeze Airways
Deal found 5/6$230
This Mytrip deal was found by Cheapflights users on 5/7. 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.
Fri 7/315:30 pm
PNS
-
ORF
1 stop26h 09m
Frontier
Sun 8/29:35 pm
ORF
-
PNS
1 stop19h 58m
Frontier
Deal found 5/7$261
This Mytrip deal was found by Cheapflights users on 5/7. 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.
Fri 7/315:30 pm
PNS
-
ORF
1 stop26h 09m
Frontier
Mon 8/39:35 pm
ORF
-
PNS
1 stop17h 43m
Frontier
Deal found 5/7$281
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 7/311:17 pm
PNS
-
ORF
1 stop8h 31m
Multiple Airlines
Tue 8/412:21 pm
ORF
-
PNS
2 stops21h 25m
Multiple Airlines
Deal found 5/7$302
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 7/3012:49 pm
PNS
-
ORF
1 stop10h 04m
Multiple Airlines
Sun 8/212:21 pm
ORF
-
PNS
2 stops31h 31m
Multiple Airlines
Deal found 5/7$305
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 7/311:17 pm
PNS
-
ORF
1 stop8h 31m
Multiple Airlines
Fri 8/712:21 pm
ORF
-
PNS
2 stops21h 25m
Multiple Airlines
Deal found 5/7$307
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 8/71:17 pm
PNS
-
ORF
1 stop8h 31m
Breeze Airways
Mon 8/107:00 am
ORF
-
PNS
2 stops12h 52m
Breeze Airways
Deal found 5/5$314
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 11/41:25 pm
PNS
-
ORF
1 stop8h 04m
Multiple Airlines
Sat 11/76:10 pm
ORF
-
PNS
1 stop18h 55m
Multiple Airlines
Deal found 5/6$316
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 7/311:17 pm
PNS
-
ORF
1 stop8h 31m
Multiple Airlines
Sun 8/212:21 pm
ORF
-
PNS
2 stops20h 25m
Multiple Airlines
Deal found 5/7$330
This Delta deal was found by Cheapflights users on 5/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/24:35 pm
PNS
-
ORF
1 stop4h 12m
Delta
Wed 6/35:20 am
ORF
-
PNS
1 stop4h 14m
Delta
Deal found 5/4$335

Find flight deals from Pensacola to Chesapeake

Keep the following information in mind while searching for Pensacola to Chesapeake flight deals. Data was last updated May 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$261
(Mytrip)

One-way from

$81
(Kiwi.com)

Popular in

February

Cheapest in

August

Average price

$405
Provider with most accurate pricing for Pensacola-Norfolk flight deals.
Provider most trusted by Cheapflights users for Pensacola-Norfolk flights.
From Pensacola to Chesapeake
One-way flight from Pensacola to Chesapeake
Highest demand for flights based on searches. 8% potential increase in price ($36 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in May 2026

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 May 8, 2026.
Use the filters below to find and compare flights from Pensacola to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Tue 6/2

4:35 pm-9:47 pm

1 stop4h 12m

Norfolk

Wed 6/3

5:20 am-8:34 am

1 stop4h 14m

$335

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 6/25

11:05 am-6:35 pm

2 stops6h 30m

Norfolk

Tue 6/30

12:25 pm-7:55 pm

2 stops8h 30m

$381

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 7/22

7:50 am-3:50 pm

1 stop7h 00m

Norfolk

Sat 7/25

9:55 am-3:40 pm

1 stop6h 45m

$407

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 6/19

11:05 am-10:00 pm

2 stops9h 55m

Norfolk

Tue 6/23

12:25 pm-7:55 pm

2 stops8h 30m

$432

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 7/15

7:50 am-6:20 pm

2 stops9h 30m

Norfolk

Sun 7/19

2:45 pm-9:05 pm

2 stops7h 20m

$443

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 6/25

12:11 pm-6:23 pm

1 stop5h 12m

Norfolk

Sun 6/28

6:04 am-12:20 pm

1 stop7h 16m

$453

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sat 5/23

8:00 am-4:40 pm

1 stop7h 40m

Norfolk

Mon 5/25

6:35 am-3:40 pm

2 stops10h 05m

$458

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sun 5/31

10:45 am-11:20 pm

2 stops11h 35m

Norfolk

Sat 6/6

1:10 pm-7:10 pm

2 stops7h 00m

$484

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 5/21

7:15 am-4:50 pm

2 stops8h 35m

Norfolk

Mon 6/1

1:00 pm-7:35 pm

1 stop7h 35m

$504
Cheapest one-way

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sat 6/27

7:33 pm-11:26 am

2 stops38h 53m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 21 resultsSorted by cheapest first
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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

How much does it cost to fly round-trip from Pensacola 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 May 8, 2026.
Read reviews from past customers who have flown Delta,American Airlines, andSpirit Airlines from Pensacola to Chesapeake. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Food

7.2

Overall

7.9

Comfort

7.9

Entertainment

7.8

Crew

8.5

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.

Food

7.2

Overall

7.9

Comfort

7.9

Entertainment

7.8

Crew

8.5

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.

Food

7.2

Overall

7.9

Comfort

7.9

Entertainment

7.8

Crew

8.5

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.

Food

7.2

Overall

7.9

Comfort

7.9

Entertainment

7.8

Crew

8.5

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 4h 12m. Fly via Delta or Southwest to get the fastest option. The distance between Pensacola and Chesapeake is about 770 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $98 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.

See more FAQs

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Alternative routes for Pensacola to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.

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 May 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$176Average$405FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$379FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$218Average$305FlexibilityNo cancel feeOn-time65%

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