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Chesapeake

$90+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — RIC
Jul 23 — Jul 301
Wed 7/23
Wed 7/30
1 adult, Economy
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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 18, 2025.

Round-trip from

$140
(Kiwi.com)

One-way from

$90
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$366
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. 21% potential increase in price ($104 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 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 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2211:05 amPNS - ORF
1 stop4h 14mBreeze Airways
Mon 8/257:00 amORF - PNS
1 stop4h 25mBreeze Airways
Deal found 7/16$140
This FlightHub deal was found by Cheapflights users on 7/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/14:44 pmPNS - ORF
1 stop5h 04mSpirit Airlines
Sun 10/55:24 amORF - PNS
1 stop11h 15mSpirit Airlines
Deal found 7/17$217
This Delta deal was found by Cheapflights users on 7/15. 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.
Thu 8/74:37 pmPNS - ORF
1 stop5h 58mDelta
Mon 8/113:30 pmORF - PNS
1 stop4h 13mDelta
Deal found 7/15$237
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Mon 8/115:41 pmPNS - ORF
1 stop5h 18mAmerican Airlines
Tue 8/128:36 amORF - PNS
2 stops6h 52mAmerican Airlines
Deal found 7/15$242
This Southwest deal was found by Cheapflights users on 7/16. 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 10/17:35 amPNS - ORF
2 stops8h 40mSouthwest
Mon 10/61:10 pmORF - PNS
2 stops9h 45mSouthwest
Deal found 7/16$253
This United Airlines deal was found by Cheapflights users on 7/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2011:00 amPNS - ORF
2 stops11h 50mUnited Airlines
Fri 8/226:15 amORF - PNS
2 stops10h 58mUnited Airlines
Deal found 7/17$262
This Mytrip deal was found by Cheapflights users on 7/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/51:53 pmPNS - ORF
2 stops7h 42mMultiple Airlines
Thu 8/79:05 amORF - PNS
1 stop10h 24mMultiple Airlines
Deal found 7/17$273

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 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

Fri 8/22

11:05 am-4:19 pm

1 stop4h 14m

Norfolk

Mon 8/25

7:00 am-10:25 am

1 stop4h 25m

$140

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 10/1

4:44 pm-10:48 pm

1 stop5h 04m

Norfolk

Sun 10/5

5:24 am-3:39 pm

1 stop11h 15m

$217

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 8/7

4:37 pm-11:35 pm

1 stop5h 58m

Norfolk

Mon 8/11

3:30 pm-6:43 pm

1 stop4h 13m

$237

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Mon 8/11

5:41 pm-11:59 pm

1 stop5h 18m

Norfolk

Tue 8/12

8:36 am-2:28 pm

2 stops6h 52m

$242

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 10/1

7:35 am-5:15 pm

2 stops8h 40m

Norfolk

Mon 10/6

1:10 pm-9:55 pm

2 stops9h 45m

$253

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 8/20

11:00 am-11:50 pm

2 stops11h 50m

Norfolk

Fri 8/22

6:15 am-4:13 pm

2 stops10h 58m

$262

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Tue 8/5

1:53 pm-10:35 pm

2 stops7h 42m

Norfolk

Thu 8/7

9:05 am-6:29 pm

1 stop10h 24m

$273

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 8/22

11:05 am-4:19 pm

1 stop4h 14m

$90

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 8/6

3:31 pm-10:56 pm

1 stop6h 25m

$119

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 8/6

7:35 am-3:00 pm

2 stops6h 25m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/17

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

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 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.

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 July 18, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Breeze Airways from Pensacola to Chesapeake. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,959 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Breeze Airways
8.0
Very good
187 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,864 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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?

    $90 is the cheapest one-way deal found within the past few days, from Breeze Airways. You may also be able to find cheap deals on American Airlines 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$109Average$253FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$211Average$366FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$236Average$419FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$376FlexibilityNo cancel feeOn-timeN/A

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