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Chesapeake

$65+ 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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — RIC
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Pensacola to Chesapeake are usually found in October or April, booked 29 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$119
(CheapOair)

One-way from

$65
(Mytrip)

Popular in

December

Cheapest in

October

Average price

$394
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. 22% potential increase in price ($109 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 February 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 February 20, 2025.

This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/199:58 amPNS - ORF
1 stop7h 48mSpirit Airlines
Wed 3/267:41 pmORF - PNS
1 stop20h 35mSpirit Airlines
Deal found 2/19$119
This Mytrip deal was found by Cheapflights users on 2/19. 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 3/73:17 pmPNS - ORF
1 stop27h 17mMultiple Airlines
Tue 3/119:30 amORF - PNS
3 stops29h 52mMultiple Airlines
Deal found 2/19$201
This Southwest deal was found by Cheapflights users on 2/19. 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 3/197:30 amPNS - ORF
1 stop6h 05mSouthwest
Wed 3/2612:05 pmORF - PNS
2 stops8h 25mSouthwest
Deal found 2/19$302
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 7/1811:01 amPNS - ORF
1 stop4h 10mBreeze Airways
Mon 7/217:00 amORF - PNS
1 stop4h 21mBreeze Airways
Deal found 2/20$305
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 3/72:10 pmPNS - ORF
1 stop6h 34mUnited Airlines
Mon 3/106:00 amORF - PNS
2 stops8h 12mUnited Airlines
Deal found 2/20$393
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 4/312:49 pmPNS - ORF
2 stops6h 35mAmerican Airlines
Sat 4/56:00 amORF - PNS
2 stops6h 43mAmerican Airlines
Deal found 2/20$408

Find flights from Pensacola to Chesapeake within your budget

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 February 20, 2025.

Fly from

Pensacola

Fly to

Chesapeake

Route

Depart

Return

Price

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 3/19

9:58 am-6:46 pm

1 stop7h 48m

Norfolk

Wed 3/26

7:41 pm-3:16 pm

1 stop20h 35m

$119

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 5/15

3:05 pm-9:54 pm

1 stop5h 49m

Norfolk

Mon 5/19

7:00 am-10:21 am

1 stop4h 21m

$199

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Wed 3/19

7:30 am-2:35 pm

1 stop6h 05m

Norfolk

Wed 3/26

12:05 pm-7:30 pm

2 stops8h 25m

$302

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Thu 5/15

5:15 am-10:07 am

1 stop3h 52m

Norfolk

Mon 5/19

6:39 am-12:08 pm

2 stops6h 29m

$353

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sun 4/13

4:25 pm-9:37 pm

Nonstop4h 12m

Norfolk

Thu 4/17

12:25 pm-3:45 pm

Nonstop4h 20m

$359

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 3/7

2:10 pm-9:44 pm

1 stop6h 34m

Norfolk

Mon 3/10

6:00 am-1:12 pm

2 stops8h 12m

$393

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sun 2/23

2:48 pm-8:29 pm

1 stop4h 41m

Norfolk

Tue 2/25

6:00 am-12:24 pm

1 stop7h 24m

$745

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Tue 3/11

3:17 pm-7:27 pm

1 stop27h 10m

$65

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Fri 3/14

5:54 pm-10:26 pm

1 stop3h 32m

$240

PensacolaNorfolk

PNS - ORF

PNSORF

Pensacola

Sat 3/15

5:31 pm-11:46 pm

1 stop5h 15m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 12 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.

Travel insights for flights from Pensacola to Chesapeake

Get recent, data-driven insights about flights from Pensacola to Chesapeake including ideal travel times, pricing trends, and more.

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 February 14, 2025.

The best time to book flights from Pensacola to Chesapeake is 29 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 February 20, 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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Breeze Airways
8.1
Very good
150 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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?

    $65 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 $240 and $285, 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 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.

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$85Average$174FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$208Average$234FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$236Average$432FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$381FlexibilityNo cancel feeOn-timeN/A
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