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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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — RIC
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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Cheapflights Tip: The best prices from Pensacola to Chesapeake are usually found in March or September, booked 83 days in advance, depart on a Tuesday or Thursday and return on a Monday

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 June 18, 2025.

Round-trip from

$217
(Delta)

One-way from

$81
(Priceline)

Popular in

December

Cheapest in

March

Average price

$464
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. 19% potential increase in price ($96 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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 June 18, 2025.

This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/64:37 pmPNS - ORF
1 stop4h 04mDelta
Tue 8/126:51 amORF - PNS
1 stop4h 59mDelta
Deal found 6/16$217
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/67:35 amPNS - ORF
1 stop5h 45mSouthwest
Tue 8/126:05 amORF - PNS
2 stops10h 30mSouthwest
Deal found 6/16$222
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/46:00 amPNS - ORF
1 stop5h 56mSpirit Airlines
Mon 7/71:51 pmORF - PNS
1 stop9h 46mSpirit Airlines
Deal found 6/16$235
This American Airlines deal was found by Cheapflights users on 6/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2010:31 amPNS - ORF
1 stop5h 54mAmerican Airlines
Wed 9/249:56 amORF - PNS
2 stops7h 56mAmerican Airlines
Deal found 6/16$247
This Mytrip deal was found by Cheapflights users on 6/18. 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 8/17:24 pmPNS - ORF
1 stop14h 52mMultiple Airlines
Thu 8/79:05 amORF - PNS
1 stop10h 24mMultiple Airlines
Deal found 6/18$261
This Priceline deal was found by Cheapflights users on 6/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2711:05 amPNS - ORF
1 stop4h 14mBreeze Airways
Mon 6/307:00 amORF - PNS
1 stop4h 25mBreeze Airways
Deal found 6/17$338
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Sat 9/201:56 pmPNS - ORF
2 stops8h 54mUnited Airlines
Wed 9/246:00 amORF - PNS
3 stops17h 00mUnited Airlines
Deal found 6/16$352

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 18, 2025.
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 8/6

4:37 pm-9:41 pm

1 stop4h 04m

Norfolk

Tue 8/12

6:51 am-10:50 am

1 stop4h 59m

$217

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 8/6

7:35 am-2:20 pm

1 stop5h 45m

Norfolk

Tue 8/12

6:05 am-3:35 pm

2 stops10h 30m

$222

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 7/4

6:00 am-12:56 pm

1 stop5h 56m

Norfolk

Mon 7/7

1:51 pm-10:37 pm

1 stop9h 46m

$235

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sat 9/20

10:31 am-5:25 pm

1 stop5h 54m

Norfolk

Wed 9/24

9:56 am-4:52 pm

2 stops7h 56m

$247

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 8/1

7:24 pm-11:16 am

1 stop14h 52m

Norfolk

Thu 8/7

9:05 am-6:29 pm

1 stop10h 24m

$261

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sat 9/20

1:56 pm-11:50 pm

2 stops8h 54m

Norfolk

Wed 9/24

6:00 am-10:00 pm

3 stops17h 00m

$352

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 6/26

9:28 am-3:19 pm

1 stop4h 51m

$81

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 9/24

1:59 pm-9:26 pm

1 stop6h 27m

$109

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 9/24

6:25 am-2:51 pm

2 stops7h 26m

$114

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 7/4

2:08 pm-11:44 pm

2 stops8h 36m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 13 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

How far ahead should I book a flight from Pensacola to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Pensacola to Chesapeake. Price data was last updated on June 13, 2025.

The best time to book flights from Pensacola to Chesapeake is 81 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, January is the cheapest month in which you can book a flight from Pensacola to Chesapeake (average of $281). Flying from Pensacola to Chesapeake in March is currently the most expensive (average of $351). 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 PNS to C6E?

Find hourly flight availability from Pensacola 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 June 18, 2025.

When flying from Pensacola to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chesapeake ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Chesapeake when rainfall is around 2.9 in.

Temperature in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chesapeake, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

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 18, 2025.
Get a feel of what it's like to fly with Breeze Airways, Southwest and Delta from Pensacola to Chesapeake by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
182 reviews

Crew

8.8

Entertainment

6.6

Food

6.8

Overall

8.1

Boarding

8.4

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
182 reviews
Breeze Airways
8.1
Very good
182 reviews

Crew

8.8

Entertainment

6.6

Food

6.8

Overall

8.1

Boarding

8.4

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,280 reviews
Breeze Airways
8.1
Very good
182 reviews

Crew

8.8

Entertainment

6.6

Food

6.8

Overall

8.1

Boarding

8.4

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,964 reviews
Breeze Airways
8.1
Very good
182 reviews

Crew

8.8

Entertainment

6.6

Food

6.8

Overall

8.1

Boarding

8.4

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,809 reviews
Breeze Airways
8.1
Very good
182 reviews

Crew

8.8

Entertainment

6.6

Food

6.8

Overall

8.1

Boarding

8.4

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
182 reviews

Crew

8.8

Entertainment

6.6

Food

6.8

Overall

8.1

Boarding

8.4

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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. 4 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.

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

    $81 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 Delta and American Airlines, with prices starting from $109 and $114, 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, January is the cheapest month in which you can book a flight from Pensacola to Chesapeake (average of $281). Flying from Pensacola to Chesapeake in March is currently the most expensive (average of $351). 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 4 airlines flying from Pensacola to Chesapeake

Discover the top 4 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$133Average$211FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$211Average$366FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$236Average$428FlexibilityNo cancel feeOn-time71%
DeltaCheapest$238Average$370FlexibilityNo cancel feeOn-timeN/A

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