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Pensacola

$111+ Cheap flights from Chesapeake, VA to Pensacola (PNS)

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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
1 adult, Economy
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The best prices from Chesapeake to Pensacola are usually found in August or September, booked 36 days in advance, depart on a Monday or Wednesday and return on a Tuesday

Cheap flight deals from Chesapeake to Pensacola

Keep the following information in mind while searching for Chesapeake to Pensacola flight deals. Data was last updated February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$152
(FlightHub)

One-way from

$111
(FlightHub)

Popular in

December

Cheapest in

August

Average price

$385
Provider with most accurate pricing for Norfolk-Pensacola flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Pensacola flights.
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From Chesapeake to Pensacola
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One-way flight from Chesapeake to Pensacola
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Highest demand for flights based on searches. 9% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 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 Chesapeake to Pensacola

Cheapest flights from Chesapeake to Pensacola
Explore the most affordable flight options available from Chesapeake to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.

This Mytrip deal was found by Cheapflights users on 2/21. 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 3/197:41 pmORF - PNS
1 stop11h 55mSpirit Airlines
Mon 3/314:11 pmPNS - ORF
1 stop24h 07mSpirit Airlines
Deal found 2/21$129
This Mytrip deal was found by Cheapflights users on 2/21. 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 3/1910:45 amORF - PNS
2 stops30h 00mMultiple Airlines
Mon 3/314:11 pmPNS - ORF
1 stop24h 07mMultiple Airlines
Deal found 2/21$168
This Delta deal was found by Cheapflights users on 2/21. 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 4/245:51 pmORF - PNS
1 stop4h 34mDelta
Mon 4/287:27 pmPNS - ORF
1 stop3h 36mDelta
Deal found 2/21$332
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Fri 3/286:16 pmORF - PNS
1 stop3h 59mAmerican Airlines
Wed 4/212:49 pmPNS - ORF
2 stops6h 40mAmerican Airlines
Deal found 2/21$337
This Southwest deal was found by Cheapflights users on 2/21. 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.
Fri 3/2112:20 pmORF - PNS
2 stops11h 30mSouthwest
Fri 3/285:30 amPNS - ORF
2 stops13h 05mSouthwest
Deal found 2/21$353
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1312:25 pmORF - PNS
Nonstop4h 20mBreeze Airways
Sun 3/164:25 pmPNS - ORF
Nonstop4h 12mBreeze Airways
Deal found 2/20$356
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Sat 3/86:10 amORF - PNS
1 stop6h 01mUnited Airlines
Wed 3/122:10 pmPNS - ORF
1 stop6h 34mUnited Airlines
Deal found 2/21$408

Find flights from Chesapeake to Pensacola within your budget

Customize your flight search to find flights from Chesapeake to Pensacola 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 23, 2025.

Fly from

Chesapeake

Fly to

Pensacola

Route

Depart

Return

Price

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Wed 3/19

7:41 pm-6:36 am

1 stop11h 55m

Pensacola

Mon 3/31

4:11 pm-5:18 pm

1 stop24h 07m

$129

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Wed 3/19

10:45 am-3:45 pm

2 stops30h 00m

Pensacola

Mon 3/31

4:11 pm-5:18 pm

1 stop24h 07m

$168

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 4/24

5:51 pm-9:25 pm

1 stop4h 34m

Pensacola

Mon 4/28

7:27 pm-12:03 am

1 stop3h 36m

$332

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Fri 3/28

6:16 pm-9:15 pm

1 stop3h 59m

Pensacola

Wed 4/2

12:49 pm-8:29 pm

2 stops6h 40m

$337

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Fri 3/21

12:20 pm-10:50 pm

2 stops11h 30m

Pensacola

Fri 3/28

5:30 am-7:35 pm

2 stops13h 05m

$353

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 3/13

12:25 pm-3:45 pm

Nonstop4h 20m

Pensacola

Sun 3/16

4:25 pm-9:37 pm

Nonstop4h 12m

$356

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sat 3/8

6:10 am-11:11 am

1 stop6h 01m

Pensacola

Wed 3/12

2:10 pm-9:44 pm

1 stop6h 34m

$408

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sun 3/16

11:25 am-5:54 pm

1 stop7h 29m

$111

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sun 3/16

12:25 pm-3:45 pm

Nonstop4h 20m

$202

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sun 3/16

6:00 am-7:10 pm

2 stops14h 10m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Best time to book a flight from Chesapeake to Pensacola

Have a flexible travel schedule? Discover the best time to fly to Pensacola from Chesapeake 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 Chesapeake to Pensacola

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

How far ahead should I book a flight from Chesapeake to Pensacola?

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Pensacola. Price data was last updated on February 14, 2025.

The price you pay for your flight from Chesapeake to Pensacola may vary depending on when you book. For the best chance of a lower fare, look to book 36 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chesapeake to Pensacola?

Currently, September is the cheapest month in which you can book a flight from Chesapeake to Pensacola (average of $306). Flying from Chesapeake to Pensacola in March is currently the most expensive (average of $418). 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 C6E to PNS?

Find hourly flight availability from Chesapeake to Pensacola. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 23, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chesapeake to Pensacola as you normally would.

What is the cheapest day to fly from Chesapeake to Pensacola?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Pensacola. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chesapeake to Pensacola flight should consider departing on Monday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Pensacola by month

Plan your trip to Pensacola by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Pensacola ranges from 4.2 - 7.4 inches per month. July is typically the wettest month, when rainfall can reach 7.4 in. May is typically the driest time to visit Pensacola when rainfall is around 4.2 in.

Temperature in Pensacola by month

Plan your trip to Pensacola by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Pensacola, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

Reviews of airlines servicing Pensacola

Get insights into the airlines that provide service to Pensacola. 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 Pensacola. Reviews last updated February 23, 2025.
Southwest
8.1
Very good
4,385 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

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
4,385 reviews
Southwest
8.1
Very good
4,385 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

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
4,385 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

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
8,203 reviews
Southwest
8.1
Very good
4,385 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

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
8,754 reviews
Southwest
8.1
Very good
4,385 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

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.

Spirit Airlines
6.3
Okay
8,006 reviews
Southwest
8.1
Very good
4,385 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

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 Chesapeake to Pensacola. 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 into for flights to Pensacola from Chesapeake?

    Located just 4.0 mi from the city center, Pensacola is the airport most travelers will use when flying to Pensacola from Chesapeake. Booking flights from Chesapeake to Pensacola (PNS) should be relatively easy as there are 0 daily inbound flights from Chesapeake from 5 different airlines.

  • What are the cheapest airlines to fly from Chesapeake to Pensacola one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $111. Breeze Airways flights start at $219 while deals on United Airlines start at $277 one-way.

  • Can I find deals for flights from Chesapeake to Pensacola that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Pensacola flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Pensacola?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Pensacola.

  • Can I find deals for business class flights from Chesapeake to Pensacola?

    Yes. Cheapflights offers flight deals from Chesapeake to Pensacola 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 Chesapeake to Pensacola?

    Currently, September is the cheapest month in which you can book a flight from Chesapeake to Pensacola (average of $306). Flying from Chesapeake to Pensacola in March is currently the most expensive (average of $418). 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

Traveling to a place near Chesapeake?

Book flights to Chesapeake if you plan to visit one of these locations
Navarre
Foley
Perdido Key
Milton
Atmore
Navarre Beach
Warrington

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chesapeake to Pensacola

Discover the top 5 airlines that operate flights from Chesapeake to Pensacola. 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 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$120Average$194FlexibilityNo cancel feeOn-time65%
DeltaCheapest$246Average$406FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$249Average$303FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$260Average$455FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$306Average$447FlexibilityNo cancel feeOn-time63%
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