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Pensacola

$93+ 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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Pensacola are usually found in August or May, booked 85 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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$205
(Cheapflightsfares)

One-way from

$93
(Mytrip)

Popular in

December

Cheapest in

August

Average price

$406
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. 10% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Mytrip deal was found by Cheapflights users on 4/22. 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 5/2712:13 pmORF - PNS
1 stop11h 07mSpirit Airlines
Tue 6/36:00 amPNS - ORF
1 stop27h 29mSpirit Airlines
Deal found 4/22$180
This Mytrip deal was found by Cheapflights users on 4/23. 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 6/187:32 pmORF - PNS
1 stop24h 59mMultiple Airlines
Sat 6/219:23 amPNS - ORF
1 stop21h 52mMultiple Airlines
Deal found 4/23$242
This Delta deal was found by Cheapflights users on 4/23. 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 6/267:51 pmORF - PNS
1 stop4h 33mDelta
Mon 6/304:07 pmPNS - ORF
1 stop4h 26mDelta
Deal found 4/23$303
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Sat 6/75:49 pmORF - PNS
1 stop4h 14mAmerican Airlines
Sat 6/145:10 pmPNS - ORF
1 stop5h 24mAmerican Airlines
Deal found 4/23$318
This Southwest deal was found by Cheapflights users on 4/23. 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.
Sat 8/166:20 amORF - PNS
2 stops11h 45mSouthwest
Tue 8/197:35 amPNS - ORF
1 stop5h 45mSouthwest
Deal found 4/23$322
This United Airlines deal was found by Cheapflights users on 4/23. 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 5/146:15 amORF - PNS
2 stops13h 04mUnited Airlines
Sat 5/172:05 pmPNS - ORF
2 stops8h 41mUnited Airlines
Deal found 4/23$418

Cheapflights Fare Finder

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 April 24, 2025.
Use the filters below to find and compare flights from Chesapeake to Pensacola that are best for you.

Fly from

Chesapeake

Fly to

Pensacola

Route

Depart

Return

Price

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Wed 5/14

12:13 pm-10:20 pm

1 stop11h 07m

Pensacola

Sat 5/17

8:20 am-2:16 pm

1 stop4h 56m

$205

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Wed 6/18

7:32 pm-7:31 pm

1 stop24h 59m

Pensacola

Wed 6/25

9:00 am-8:15 am

1 stop22h 15m

$241

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 6/26

7:51 pm-11:24 pm

1 stop4h 33m

Pensacola

Mon 6/30

1:38 pm-9:33 pm

1 stop6h 55m

$303

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sat 6/7

5:49 pm-9:03 pm

1 stop4h 14m

Pensacola

Sat 6/14

5:10 pm-11:34 pm

1 stop5h 24m

$318

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sat 8/16

6:20 am-5:05 pm

2 stops11h 45m

Pensacola

Tue 8/19

7:35 am-2:20 pm

1 stop5h 45m

$322

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Wed 5/14

6:15 am-6:19 pm

2 stops13h 04m

Pensacola

Sat 5/17

2:05 pm-11:46 pm

2 stops8h 41m

$418

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Wed 5/21

12:13 pm-10:20 pm

1 stop11h 07m

$93

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sat 5/31

8:02 am-2:07 pm

2 stops31h 05m

$422

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Pensacola

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 April 18, 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 85 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 April 24, 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 April 24, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines 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
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,685 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Spirit Airlines
6.3
Okay
7,940 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • 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
Gulf Breeze
Navarre
Foley
Perdido Key
Milton
Atmore
Navarre Beach
Warrington

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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$109Average$195FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$157Average$303FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$238Average$404FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$455FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$296Average$447FlexibilityNo cancel feeOn-time63%

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