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Chesapeake

$114+ 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 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — RIC
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$200
(Kiwi.com)

One-way from

$114
(FlightHub)

Popular in

December

Cheapest in

March

Average price

$382
From Pensacola to Chesapeake
Search Deals
One-way flight from Pensacola to Chesapeake
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Highest demand for flights based on searches. 20% potential increase in price ($101 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
Mon 8/1811:05 amPNS - ORF
1 stop4h 14mBreeze Airways
Mon 8/257:00 amORF - PNS
1 stop4h 25mBreeze Airways
Deal found 7/3$200
This American Airlines deal was found by Cheapflights users on 7/3. 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
1 stop4h 42mAmerican Airlines
Wed 10/88:30 amORF - PNS
1 stop5h 06mAmerican Airlines
Deal found 7/3$237
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Sat 7/193:06 pmPNS - ORF
1 stop6h 29mSpirit Airlines
Sat 7/2612:11 pmORF - PNS
1 stop7h 18mSpirit Airlines
Deal found 6/30$241
This Southwest deal was found by Cheapflights users on 7/3. 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.
Mon 8/181:45 pmPNS - ORF
2 stops6h 40mSouthwest
Mon 8/255:30 amORF - PNS
2 stops8h 30mSouthwest
Deal found 7/3$247
This Delta deal was found by Cheapflights users on 7/2. 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.
Mon 9/295:48 pmPNS - ORF
1 stop4h 01mDelta
Fri 10/35:55 pmORF - PNS
1 stop6h 13mDelta
Deal found 7/2$277
This Mytrip deal was found by Cheapflights users on 7/3. 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 7/301:53 pmPNS - ORF
2 stops7h 42mMultiple Airlines
Thu 7/319:05 amORF - PNS
1 stop10h 24mMultiple Airlines
Deal found 7/3$299
This United Airlines deal was found by Cheapflights users on 7/1. 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 9/311:00 amPNS - ORF
2 stops11h 53mUnited Airlines
Sat 9/66:30 amORF - PNS
2 stops10h 43mUnited Airlines
Deal found 7/1$332

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 July 3, 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

Mon 8/18

11:05 am-4:19 pm

1 stop4h 14m

Norfolk

Mon 8/25

7:00 am-10:25 am

1 stop4h 25m

$200

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 10/1

8:00 am-1:42 pm

1 stop4h 42m

Norfolk

Wed 10/8

8:30 am-12:36 pm

1 stop5h 06m

$237

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sat 7/19

3:06 pm-10:35 pm

1 stop6h 29m

Norfolk

Sat 7/26

12:11 pm-6:29 pm

1 stop7h 18m

$241

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Mon 8/18

1:45 pm-9:25 pm

2 stops6h 40m

Norfolk

Mon 8/25

5:30 am-1:00 pm

2 stops8h 30m

$247

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Mon 9/29

5:48 pm-10:49 pm

1 stop4h 01m

Norfolk

Fri 10/3

5:55 pm-11:08 pm

1 stop6h 13m

$277

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 7/30

1:53 pm-10:35 pm

2 stops7h 42m

Norfolk

Thu 7/31

9:05 am-6:29 pm

1 stop10h 24m

$299

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 9/3

11:00 am-11:53 pm

2 stops11h 53m

Norfolk

Sat 9/6

6:30 am-4:13 pm

2 stops10h 43m

$332

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sat 7/26

3:06 pm-10:35 pm

1 stop6h 29m

$114

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 8/27

2:13 pm-9:12 pm

1 stop5h 59m

$119

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 8/27

7:35 am-5:15 pm

2 stops8h 40m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 13 results
1
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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 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 27, 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 July 3, 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.

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 July 3, 2025.
Read reviews from past customers who have flown Breeze Airways, Southwest, and Delta from Pensacola to Chesapeake. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

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
183 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

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
4,270 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

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
7,970 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

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
8,845 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

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
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

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?

    $114 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 Southwest, with prices starting from $119 and $124, 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$109Average$226FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$211Average$366FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$236Average$420FlexibilityNo cancel feeOn-time71%
DeltaCheapest$238Average$368FlexibilityNo cancel feeOn-timeN/A

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