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Chesapeake

$83+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — RIC
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
1 adult, Economy
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Cheapflights Tip: The best prices from Pensacola to Chesapeake are usually found in October or September, booked 47 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 April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$206
(Mytrip)

One-way from

$83
(Priceline)

Popular in

March

Cheapest in

October

Average price

$316
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. 4% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 2, 2025.

This Mytrip deal was found by Cheapflights users on 4/1. 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.
Wed 6/114:35 pmPNS - ORF
1 stop17h 10mMultiple Airlines
Wed 6/257:33 pmORF - PNS
1 stop24h 58mMultiple Airlines
Deal found 4/1$206
This Mytrip deal was found by Cheapflights users on 4/1. 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.
Wed 4/303:59 pmPNS - ORF
1 stop27h 02mSpirit Airlines
Sun 5/48:56 pmORF - PNS
1 stop19h 08mSpirit Airlines
Deal found 4/1$213
This Southwest deal was found by Cheapflights users on 4/1. 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.
Tue 4/298:00 amPNS - ORF
1 stop5h 30mSouthwest
Tue 5/612:25 pmORF - PNS
1 stop4h 15mSouthwest
Deal found 4/1$271
This Delta deal was found by Cheapflights users on 4/1. 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 6/107:00 amPNS - ORF
1 stop4h 40mDelta
Tue 6/2410:07 amORF - PNS
1 stop5h 51mDelta
Deal found 4/1$284
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 6/1311:05 amPNS - ORF
1 stop4h 14mBreeze Airways
Fri 6/277:00 amORF - PNS
1 stop4h 25mBreeze Airways
Deal found 4/1$327
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Wed 5/76:30 amPNS - ORF
2 stops9h 11mUnited Airlines
Sat 5/106:10 amORF - PNS
2 stops13h 46mUnited Airlines
Deal found 4/1$383
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Tue 4/1511:17 amPNS - ORF
1 stop3h 21mAmerican Airlines
Fri 4/184:27 pmORF - PNS
1 stop4h 02mAmerican Airlines
Deal found 4/1$427

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 April 2, 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 6/11

4:35 pm-10:45 am

1 stop17h 10m

Norfolk

Wed 6/25

7:33 pm-7:31 pm

1 stop24h 58m

$206

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 4/30

3:59 pm-8:01 pm

1 stop27h 02m

Norfolk

Sun 5/4

8:56 pm-3:04 pm

1 stop19h 08m

$213

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Tue 4/29

8:00 am-2:30 pm

1 stop5h 30m

Norfolk

Tue 5/6

12:25 pm-3:40 pm

1 stop4h 15m

$271

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Tue 6/10

7:00 am-12:40 pm

1 stop4h 40m

Norfolk

Tue 6/24

10:07 am-2:58 pm

1 stop5h 51m

$284

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 6/13

11:05 am-4:19 pm

1 stop4h 14m

Norfolk

Fri 6/27

7:00 am-10:25 am

1 stop4h 25m

$327

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 5/7

6:30 am-4:41 pm

2 stops9h 11m

Norfolk

Sat 5/10

6:10 am-6:56 pm

2 stops13h 46m

$383

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Tue 4/15

11:17 am-3:38 pm

1 stop3h 21m

Norfolk

Fri 4/18

4:27 pm-7:29 pm

1 stop4h 02m

$427

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 5/1

2:25 pm-8:01 pm

1 stop4h 36m

$83

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sun 4/6

4:25 pm-9:40 am

2 stops16h 15m

$266

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sun 4/27

6:30 am-2:26 pm

2 stops30h 56m

$427

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 March 28, 2025.

The best time to book flights from Pensacola to Chesapeake is 47 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 June is currently the most expensive (average of $372). 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 April 2, 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 April 2, 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
157 reviews

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.3

Food

6.7

Overall

8.1

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
157 reviews
Breeze Airways
8.1
Very good
157 reviews

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.3

Food

6.7

Overall

8.1

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
4,272 reviews
Breeze Airways
8.1
Very good
157 reviews

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.3

Food

6.7

Overall

8.1

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
7,898 reviews
Breeze Airways
8.1
Very good
157 reviews

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.3

Food

6.7

Overall

8.1

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
8,615 reviews
Breeze Airways
8.1
Very good
157 reviews

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.3

Food

6.7

Overall

8.1

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
157 reviews

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.3

Food

6.7

Overall

8.1

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.

  • 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 June is currently the most expensive (average of $372). 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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See prices for flight routes from nearby airports that may be better suited for you.
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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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$85Average$186FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$208Average$234FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$236Average$447FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$373FlexibilityNo cancel feeOn-timeN/A

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