HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Pensacola

$60+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to Pensacola with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Chesapeake to Pensacola are usually found in January or February, booked 37 days in advance, depart on a Monday or Wednesday and return on a Tuesday

Cheap flight deals from Chesapeake to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from Chesapeake (C6E) to Pensacola (PNS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$139
(Mytrip)

One-way from

$60
(Cheapflightsfares)

Popular in

December

Cheapest in

January

Average price

$500
From Chesapeake to Pensacola
Search Deals
One-way flight from Chesapeake to Pensacola
Search Deals
High demand for flights, 7% potential price rise
Search Deals
Best time to find cheap flights, 3% potential price drop
Search Deals
Average for round-trip flights in December 2024
Search Deals

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 December 18, 2024.

This CheapOair deal was found by Cheapflights users on 12/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/319:45 amORF - PNS
1 stop9h 20mSpirit Airlines
Tue 1/77:07 pmPNS - ORF
1 stop27h 08mSpirit Airlines
Deal found 12/16$301
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:52 amORF - PNS
1 stop5h 39mAmerican Airlines
Tue 1/712:55 pmPNS - ORF
2 stops7h 30mAmerican Airlines
Deal found 12/16$422
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:00 amORF - PNS
2 stops14h 10mUnited Airlines
Tue 1/72:31 pmPNS - ORF
1 stop5h 59mUnited Airlines
Deal found 12/17$424
This Mytrip deal was found by Cheapflights users on 12/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/298:23 pmORF - PNS
2 stops18h 30mMultiple Airlines
Wed 1/17:00 pmPNS - ORF
1 stop12h 50mMultiple Airlines
Deal found 12/16$482
This Delta deal was found by Cheapflights users on 12/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2011:00 amORF - PNS
1 stop6h 37mDelta
Fri 12/2710:13 amPNS - ORF
1 stop5h 45mDelta
Deal found 12/16$937

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sun 1/12

12:24 pm-3:44 pm

1 stop4h 20m

Pensacola

Thu 1/16

4:24 pm-9:36 pm

1 stop4h 12m

$139

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Mon 1/13

5:25 am-6:40 pm

1 stop14h 15m

Pensacola

Thu 1/16

7:35 pm-11:59 pm

1 stop27h 24m

$143

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 2/20

12:25 pm-3:45 pm

1 stop4h 20m

Pensacola

Sun 2/23

5:37 pm-11:21 pm

1 stop4h 44m

$225

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Tue 2/11

3:00 pm-8:05 pm

1 stop6h 05m

Pensacola

Wed 2/19

6:00 am-12:11 pm

1 stop5h 11m

$296

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Tue 2/11

11:43 am-10:00 pm

2 stops11h 17m

Pensacola

Wed 2/19

3:10 pm-11:46 pm

1 stop7h 36m

$371

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Tue 1/14

9:54 am-4:12 pm

2 stops7h 18m

Pensacola

Fri 1/17

11:13 am-6:44 pm

2 stops6h 31m

$376

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 5/15

11:45 am-8:10 pm

2 stops9h 25m

Pensacola

Mon 5/19

6:00 am-2:30 pm

1 stop7h 30m

$473

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Wed 1/22

5:25 am-1:23 pm

1 stop8h 58m

$60

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sun 1/19

12:24 pm-3:44 pm

1 stop4h 20m

$82

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Tue 1/21

5:00 am-10:33 am

1 stop6h 33m

$153

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 13 results
1
2

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 December 13, 2024.

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 37 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 $296). Flying from Chesapeake to Pensacola in March is currently the most expensive (average of $380). 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 December 18, 2024.

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 December 18, 2024.
Read reviews from past customers who have flown American Airlines, United Airlines and Delta from Chesapeake to Pensacola. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Breeze Airways
8.1
Very good
135 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,055 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 4 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 $60. Breeze Airways flights start at $82 while deals on American Airlines start at $153 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 $296). Flying from Chesapeake to Pensacola in March is currently the most expensive (average of $380). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chesapeake to Pensacola

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Orlando flights
Reagan-National to Miami flights
Reagan-National to Orlando flights
Dulles Intl to Miami flights
Dulles Intl to Fort Lauderdale flights
Reagan-National to Fort Lauderdale flights
Dulles Intl to Tampa flights
Reagan-National to Tampa flights
Raleigh to Orlando flights
Raleigh to Miami flights
Dulles Intl to West Palm Beach flights
Raleigh to Fort Lauderdale flights
Dulles Intl to Fort Myers flights
Reagan-National to West Palm Beach flights
Dulles Intl to Key West flights
Richmond to Orlando flights
Reagan-National to Fort Myers flights
Richmond to Fort Lauderdale flights
Reagan-National to Sarasota flights
Raleigh to Tampa flights
Dulles Intl to Jacksonville flights
Reagan-National to Key West flights
Richmond to Miami flights
Reagan-National to Jacksonville flights
Norfolk to Orlando flights
Norfolk to Miami flights
Dulles Intl to Sarasota flights
Greensboro to Orlando flights
Greensboro to Miami flights
Norfolk to Fort Lauderdale flights
Reagan-National to Valparaiso flights
Reagan-National to Pensacola flights
Dulles Intl to Pensacola flights
Dulles Intl to Daytona Beach flights
Dulles Intl to Panama City flights
Norfolk to Tampa flights
Dulles Intl to Valparaiso flights
Raleigh to Fort Myers flights
Reagan-National to Daytona Beach flights
Richmond to Tampa flights
Reagan-National to Panama City flights
Reagan-National to Melbourne flights
Dulles Intl to Melbourne flights
Greensboro to Fort Lauderdale flights
Greensboro to Tampa flights
Raleigh to Key West flights
Raleigh to Jacksonville flights
Raleigh to West Palm Beach flights
Charlottesville to Orlando flights
Richmond to Jacksonville flights

Top 4 airlines flying from Chesapeake to Pensacola

Discover the top 4 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$91Average$186FlexibilityNo cancel feeOn-time65%
DeltaCheapest$246Average$404FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$249Average$303FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$260Average$475FlexibilityNo cancel feeOn-time71%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.