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Pensacola

$95+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Pensacola are usually found in September or May, booked 28 days in advance, depart on a Monday or Wednesday and return on a Tuesday

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 octubre 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
jue. 11/139:03 pmORF - PNS
1 stop14h 19mSpirit Airlines
dom. 11/1611:17 amPNS - ORF
1 stop24h 07mSpirit Airlines
Deal found 10/27$213
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
mié. 11/269:26 pmORF - PNS
1 stop16h 23mSpirit Airlines
lun. 12/15:54 pmPNS - ORF
1 stop25h 37mSpirit Airlines
Deal found 10/27$217
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
lun. 11/248:02 pmORF - PNS
1 stop24h 09mSpirit Airlines
lun. 12/15:54 pmPNS - ORF
1 stop25h 37mSpirit Airlines
Deal found 10/27$221
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
jue. 11/133:20 pmORF - PNS
2 stops20h 02mMultiple Airlines
dom. 11/1611:17 amPNS - ORF
1 stop24h 07mMultiple Airlines
Deal found 10/27$226
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
dom. 11/99:03 pmORF - PNS
1 stop14h 19mSpirit Airlines
mar. 11/118:16 pmPNS - ORF
1 stop21h 42mSpirit Airlines
Deal found 10/28$250
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
mar. 11/117:53 pmORF - PNS
1 stop24h 18mMultiple Airlines
sáb. 11/154:44 pmPNS - ORF
2 stops15h 03mMultiple Airlines
Deal found 10/27$267
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
mié. 11/269:26 pmORF - PNS
1 stop16h 23mSpirit Airlines
dom. 11/308:16 pmPNS - ORF
2 stops23h 15mSpirit Airlines
Deal found 10/28$285

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 octubre 29, 2025.

Most accurate provider

Gotogate
3 stars

Most trusted provider

Gotogate
3 stars

Round-trip from

$212
(Breeze Airways)

One-way from

$95
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$446
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
Search Deals
One-way flight from Chesapeake to Pensacola
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($100 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 octubre 29, 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

dom. 11/9

9:03 pm-10:22 am

1 stop14h 19m

Pensacola

mar. 11/11

8:16 pm-6:58 pm

1 stop21h 42m

$250

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

vie. 11/28

9:26 pm-7:11 pm

2 stops22h 45m

Pensacola

lun. 12/1

8:16 pm-8:31 pm

2 stops23h 15m

$274

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

vie. 12/12

7:00 am-2:55 pm

1 stop8h 55m

Pensacola

dom. 12/14

7:09 pm-7:16 pm

1 stop23h 07m

$301

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

mié. 11/26

9:26 pm-12:49 pm

1 stop16h 23m

Pensacola

dom. 11/30

1:44 pm-9:43 am

1 stop18h 59m

$302

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

mié. 11/5

6:33 pm-10:22 am

1 stop16h 49m

Pensacola

mié. 11/12

4:44 pm-8:47 am

2 stops15h 03m

$313

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

mié. 11/26

9:26 pm-12:49 pm

1 stop16h 23m

Pensacola

dom. 11/30

8:16 pm-8:31 pm

2 stops23h 15m

$313

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

dom. 12/21

5:23 am-9:41 am

1 stop5h 18m

Pensacola

jue. 12/25

6:00 am-11:17 am

1 stop4h 17m

$324

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

vie. 11/28

7:00 am-3:23 pm

1 stop9h 23m

Pensacola

lun. 12/1

5:54 pm-8:31 pm

1 stop25h 37m

$361

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

mar. 12/9

6:05 am-1:17 pm

1 stop8h 12m

Pensacola

mié. 12/10

2:15 pm-9:00 pm

1 stop5h 45m

$383

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

dom. 12/21

3:25 pm-10:50 pm

2 stops8h 25m

Pensacola

jue. 12/25

7:20 am-5:35 pm

2 stops9h 15m

$427

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 17 results
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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 October 24, 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 28 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, February is the cheapest month in which you can book a flight from Chesapeake to Pensacola (average of $87). Flying from Chesapeake to Pensacola in November is currently the most expensive (average of $255). 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 octubre 29, 2025.

One of the essential ways to save on airfare from Chesapeake to Pensacola is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 31% on airfare.

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. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 octubre 29, 2025.
Get a feel of what it's like to fly with Breeze Airways, Delta, and American Airlines from Chesapeake to Pensacola by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
221 reviews

Boarding

8.3

Crew

8.7

Overall

8.1

Food

6.7

Entertainment

6.6

Comfort

8.2

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.1
Very good
221 reviews
Breeze Airways
8.1
Very good
221 reviews

Boarding

8.3

Crew

8.7

Overall

8.1

Food

6.7

Entertainment

6.6

Comfort

8.2

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Delta
7.9
Good
7,993 reviews
Breeze Airways
8.1
Very good
221 reviews

Boarding

8.3

Crew

8.7

Overall

8.1

Food

6.7

Entertainment

6.6

Comfort

8.2

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
American Airlines
7.2
Good
11,032 reviews
Breeze Airways
8.1
Very good
221 reviews

Boarding

8.3

Crew

8.7

Overall

8.1

Food

6.7

Entertainment

6.6

Comfort

8.2

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Spirit Airlines
6.3
Okay
8,113 reviews
Breeze Airways
8.1
Very good
221 reviews

Boarding

8.3

Crew

8.7

Overall

8.1

Food

6.7

Entertainment

6.6

Comfort

8.2

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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.

  • How long is the flight from Chesapeake to Pensacola?

    For as low as $250, Spirit Airlines can have you in Pensacola from Chesapeake in 14h 19m. There are 770 mi between Chesapeake and Pensacola.

  • 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 $117. American Airlines flights start at $131 while deals on Delta start at $131 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, February is the cheapest month in which you can book a flight from Chesapeake to Pensacola (average of $87). Flying from Chesapeake to Pensacola in November is currently the most expensive (average of $255). 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 Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Gulf Breeze
Navarre
Foley
Perdido Key
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 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 octubre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$87Average$220FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$154Average$326FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$218Average$441FlexibilityNo cancel feeOn-time71%
DeltaCheapest$251Average$417FlexibilityNo cancel feeOn-timeN/A

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