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Chesapeake

$118+ 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 7/24. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — RIC
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 12, 2025.

Round-trip from

$210
(Kiwi.com)

One-way from

$118
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$461
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 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Fri 7/1811:05 amPNS - ORF
1 stop4h 14mBreeze Airways
Fri 7/257:00 amORF - PNS
1 stop4h 25mBreeze Airways
Deal found 6/10$210
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Wed 7/161:53 pmPNS - ORF
1 stop17h 22mMultiple Airlines
Tue 7/225:50 amORF - PNS
1 stop17h 51mMultiple Airlines
Deal found 6/10$237
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/246:00 amPNS - ORF
1 stop15h 35mSpirit Airlines
Fri 8/16:30 pmORF - PNS
1 stop17h 27mSpirit Airlines
Deal found 6/11$250
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 10/18:00 amPNS - ORF
2 stops7h 26mAmerican Airlines
Sun 10/51:10 pmORF - PNS
1 stop6h 04mAmerican Airlines
Deal found 6/11$323
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/12:08 pmPNS - ORF
1 stop6h 32mUnited Airlines
Mon 7/76:20 amORF - PNS
1 stop7h 46mUnited Airlines
Deal found 6/10$492
This Delta deal was found by Cheapflights users on 6/11. 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.
Fri 9/127:00 amPNS - ORF
1 stop4h 51mDelta
Tue 9/167:00 amORF - PNS
1 stop4h 46mDelta
Deal found 6/11$498
This Southwest deal was found by Cheapflights users on 6/11. 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.
Thu 6/122:25 pmPNS - ORF
1 stop8h 00mSouthwest
Sun 6/153:25 pmORF - PNS
2 stops8h 55mSouthwest
Deal found 6/11$808

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 12, 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

Fri 7/18

11:05 am-4:19 pm

1 stop4h 14m

Norfolk

Fri 7/25

7:00 am-10:25 am

1 stop4h 25m

$210

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 7/16

1:53 pm-8:15 am

1 stop17h 22m

Norfolk

Tue 7/22

5:50 am-10:41 pm

1 stop17h 51m

$237

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 7/24

6:00 am-10:35 pm

1 stop15h 35m

Norfolk

Fri 8/1

6:30 pm-10:57 am

1 stop17h 27m

$250

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 7/2

7:39 am-12:47 pm

1 stop4h 08m

Norfolk

Wed 7/9

8:27 am-1:44 pm

2 stops6h 17m

$367

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Tue 7/1

2:08 pm-9:40 pm

1 stop6h 32m

Norfolk

Mon 7/7

6:20 am-1:06 pm

1 stop7h 46m

$492

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 7/24

6:00 am-10:35 pm

1 stop15h 35m

$118

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 7/25

2:08 pm-9:40 pm

1 stop6h 32m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 9, 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 12, 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 12, 2025.
Get a feel of what it's like to fly with Breeze Airways, United Airlines and American Airlines 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
178 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

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
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

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
8,790 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

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
178 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

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!
Spirit Airlines
6.3
Okay
8,052 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

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 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 12, 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$373FlexibilityNo cancel feeOn-timeN/A

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