Chesapeake

$109+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — RIC
Jul 23 — Jul 301
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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 June 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/34:10 pm
PNS
-
ORF
1 stop4h 31m
Breeze Airways
Sat 7/47:00 am
ORF
-
PNS
1 stop6h 09m
Breeze Airways
Deal found 6/19$226
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 12/312:45 pm
PNS
-
ORF
1 stop9h 11m
Breeze Airways
Tue 12/86:00 am
ORF
-
PNS
1 stop7h 40m
Breeze Airways
Deal found 6/22$232
This Breeze Airways deal was found by Cheapflights users on 6/22. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:10 pm
PNS
-
ORF
1 stop4h 31m
Breeze Airways
Sat 7/117:00 am
ORF
-
PNS
1 stop6h 09m
Breeze Airways
Deal found 6/22$250
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 7/174:10 pm
PNS
-
ORF
1 stop4h 31m
Multiple Airlines
Sun 7/199:34 pm
ORF
-
PNS
1 stop18h 40m
Multiple Airlines
Deal found 6/20$254
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 8/214:10 pm
PNS
-
ORF
1 stop4h 31m
Multiple Airlines
Tue 8/251:20 pm
ORF
-
PNS
2 stops21h 26m
Multiple Airlines
Deal found 6/20$259
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 12/18:48 am
PNS
-
ORF
1 stop5h 16m
Breeze Airways
Sun 12/66:00 am
ORF
-
PNS
1 stop7h 05m
Breeze Airways
Deal found 6/22$262
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/138:26 pm
PNS
-
ORF
2 stops37h 55m
Multiple Airlines
Mon 8/1712:04 pm
ORF
-
PNS
1 stop4h 26m
Multiple Airlines
Deal found 6/19$265
This Kiwi.com deal was found by Cheapflights users on 6/21. 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.
Sat 9/191:25 pm
PNS
-
ORF
1 stop8h 04m
Multiple Airlines
Sun 9/2712:57 pm
ORF
-
PNS
2 stops44h 11m
Multiple Airlines
Deal found 6/21$272
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 7/298:26 am
PNS
-
ORF
1 stop11h 13m
Multiple Airlines
Sun 8/212:10 pm
ORF
-
PNS
2 stops28h 04m
Multiple Airlines
Deal found 6/21$282
This Breeze Airways deal was found by Cheapflights users on 6/22. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:18 am
PNS
-
ORF
1 stop5h 46m
Breeze Airways
Sun 9/136:00 am
ORF
-
PNS
1 stop7h 05m
Breeze Airways
Deal found 6/22$283

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 June 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$226
(Kiwi.com)

One-way from

$109
(Breeze Airways)

Popular in

May

Cheapest in

August

Average price

$376
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. 6% potential increase in price ($29 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 June 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 June 23, 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

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 7/3

4:10 pm-9:41 pm

1 stop4h 31m

Norfolk

Sat 7/11

7:00 am-12:09 pm

1 stop6h 09m

$250

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 9/10

8:18 am-3:04 pm

1 stop5h 46m

Norfolk

Sun 9/13

6:00 am-12:05 pm

1 stop7h 05m

$283

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 7/24

2:09 pm-11:44 pm

2 stops8h 35m

Norfolk

Wed 7/29

6:05 am-1:07 pm

2 stops8h 02m

$372

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 7/10

1:17 pm-11:08 pm

1 stop8h 51m

Norfolk

Sun 7/12

7:00 am-2:54 pm

1 stop8h 54m

$396
Quickest round-trip

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 7/24

6:08 pm-11:44 pm

1 stop4h 36m

Norfolk

Sun 7/26

7:59 pm-11:43 pm

1 stop4h 44m

$407

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Mon 7/13

11:05 am-10:05 pm

2 stops10h 00m

Norfolk

Wed 7/15

12:25 pm-8:00 pm

2 stops8h 35m

$423

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Tue 7/21

2:09 pm-11:44 pm

2 stops8h 35m

Norfolk

Tue 7/28

6:05 am-1:07 pm

2 stops8h 02m

$447

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Mon 11/23

1:59 pm-9:26 pm

1 stop6h 27m

Norfolk

Mon 11/30

7:40 pm-11:27 pm

1 stop4h 47m

$447

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 9/10

9:00 am-10:54 pm

2 stops12h 54m

Norfolk

Sun 9/13

6:15 am-1:09 pm

2 stops7h 54m

$464
Cheapest one-way

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 9/18

1:25 pm-10:43 pm

1 stop8h 18m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/22

Showing 1-10 of 18 resultsSorted by cheapest first
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

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 June 23, 2026.
Read reviews from past customers who have flown Delta and American Airlines from Pensacola to Chesapeake. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.8

Overall

7.8

Entertainment

7.8

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.

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.8

Overall

7.8

Entertainment

7.8

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.

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.8

Overall

7.8

Entertainment

7.8

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. 2 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 31m. Fly via Breeze Airways or United Airlines 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.

  • 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 2 airlines flying from Pensacola to Chesapeake

Discover the top 2 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 June 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$125Average$384FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$176Average$405FlexibilityNo cancel feeOn-time71%

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