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Pensacola

$135+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/166:45 am
ORF
-
PNS
1 stop11h 57m
Spirit Airlines
Thu 2/196:37 pm
PNS
-
ORF
1 stop26h 13m
Spirit Airlines
Deal found 1/28$151
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:45 am
ORF
-
PNS
1 stop11h 57m
Spirit Airlines
Tue 2/246:37 pm
PNS
-
ORF
1 stop26h 13m
Spirit Airlines
Deal found 1/27$158
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 2/241:02 pm
ORF
-
PNS
1 stop5h 40m
Multiple Airlines
Tue 3/36:37 pm
PNS
-
ORF
1 stop26h 13m
Multiple Airlines
Deal found 1/27$160
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:45 am
ORF
-
PNS
1 stop11h 57m
Spirit Airlines
Mon 3/95:20 pm
PNS
-
ORF
1 stop24h 06m
Spirit Airlines
Deal found 1/27$180
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:45 am
ORF
-
PNS
1 stop11h 57m
Spirit Airlines
Sat 3/217:00 am
PNS
-
ORF
1 stop14h 32m
Spirit Airlines
Deal found 1/28$186
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 3/248:41 pm
ORF
-
PNS
1 stop17h 43m
Multiple Airlines
Sat 3/287:00 am
PNS
-
ORF
1 stop6h 31m
Multiple Airlines
Deal found 1/27$191
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:45 am
ORF
-
PNS
1 stop11h 57m
Spirit Airlines
Mon 3/95:20 pm
PNS
-
ORF
1 stop24h 06m
Spirit Airlines
Deal found 1/27$194

Find flight deals from Chesapeake to Pensacola

Keep the following information in mind while searching for Chesapeake to Pensacola flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$151
(CheapOair)

One-way from

$135
(Cheapflightsfares)

Popular in

November

Cheapest in

September

Average price

$411
Provider with most accurate pricing for Norfolk-Pensacola flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Pensacola flights.
Search Deals
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 ($105 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Sat 2/21

6:45 am-5:42 pm

1 stop11h 57m

Pensacola

Tue 2/24

6:37 pm-9:50 pm

1 stop26h 13m

$158

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Mon 2/16

7:31 pm-5:42 pm

2 stops23h 11m

Pensacola

Thu 2/19

6:37 pm-9:50 pm

1 stop26h 13m

$176

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Tue 2/24

7:31 pm-5:42 pm

2 stops23h 11m

Pensacola

Tue 3/3

6:37 pm-9:50 pm

1 stop26h 13m

$176

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sat 3/7

6:45 am-5:42 pm

1 stop11h 57m

Pensacola

Sat 3/21

7:00 am-10:32 pm

1 stop14h 32m

$186

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Mon 3/2

6:45 am-5:42 pm

1 stop11h 57m

Pensacola

Mon 3/9

6:37 pm-6:26 pm

2 stops22h 49m

$195

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Fri 2/27

6:45 am-5:42 pm

1 stop11h 57m

Pensacola

Sun 3/1

6:37 pm-10:42 am

2 stops15h 05m

$207

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Mon 3/23

3:26 pm-9:14 pm

1 stop6h 48m

Pensacola

Sat 3/28

7:00 am-2:31 pm

1 stop6h 31m

$210

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 3/5

6:45 am-5:42 pm

1 stop11h 57m

Pensacola

Sun 3/8

6:37 pm-6:26 pm

2 stops22h 49m

$222

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 2/5

6:45 am-4:37 pm

1 stop10h 52m

$135

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 2/5

9:30 pm-10:38 am

3 stops38h 08m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 January 23, 2026.

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 January is currently the most expensive (average of $278). 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.

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 January 29, 2026.
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
8.2
Very good
263 reviews

Comfort

8.2

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.2
Very good
263 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Delta
7.9
Good
8,127 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,206 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Spirit Airlines
6.3
Okay
8,394 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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 $151, Spirit Airlines can have you in Pensacola from Chesapeake in 11h 57m. There are 770 mi between Chesapeake and Pensacola.

  • 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 January is currently the most expensive (average of $278). 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
Navarre Beach
Perdido Key
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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$87Average$194FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$127Average$285FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$218Average$428FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$416FlexibilityNo cancel feeOn-timeN/A

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