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Pensacola

$110+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Pensacola are usually found in May or September, booked 28 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 September 14, 2025.

Round-trip from

$223
(CheapOair)

One-way from

$110
(Delta)

Popular in

December

Cheapest in

May

Average price

$317
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. 11% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 14, 2025.

This CheapOair deal was found by Cheapflights users on 9/12. 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 11/107:00 amORF - PNS
1 stop8h 55mBreeze Airways
Thu 11/131:14 pmPNS - ORF
1 stop8h 44mBreeze Airways
Deal found 9/12$223
This Cheapflightsfares deal was found by Cheapflights users on 9/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:01 amORF - PNS
1 stop10h 53mSpirit Airlines
Sun 11/96:49 pmPNS - ORF
1 stop4h 18mSpirit Airlines
Deal found 9/12$224
This Cheapflightsfares deal was found by Cheapflights users on 9/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/65:24 amORF - PNS
1 stop11h 07mSpirit Airlines
Thu 10/910:28 amPNS - ORF
1 stop5h 11mSpirit Airlines
Deal found 9/12$232
This American Airlines deal was found by Cheapflights users on 9/12. 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.
Mon 10/276:26 amORF - PNS
1 stop7h 10mAmerican Airlines
Sat 11/15:00 amPNS - ORF
1 stop6h 50mAmerican Airlines
Deal found 9/12$238
This Delta deal was found by Cheapflights users on 9/12. 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.
Wed 10/15:30 amORF - PNS
1 stop3h 47mDelta
Thu 10/27:00 amPNS - ORF
1 stop3h 24mDelta
Deal found 9/12$241
This American Airlines deal was found by Cheapflights users on 9/12. 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.
Wed 10/19:56 amORF - PNS
2 stops7h 56mAmerican Airlines
Thu 10/23:57 pmPNS - ORF
1 stop6h 03mAmerican Airlines
Deal found 9/12$246
This CheapOair deal was found by Cheapflights users on 9/12. 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 9/275:20 amORF - PNS
1 stop11h 19mSpirit Airlines
Wed 10/14:44 pmPNS - ORF
1 stop5h 04mSpirit Airlines
Deal found 9/12$248
This Cheapflightsfares deal was found by Cheapflights users on 9/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:24 amORF - PNS
1 stop11h 07mSpirit Airlines
Tue 11/114:41 pmPNS - ORF
1 stop5h 59mSpirit Airlines
Deal found 9/12$255
This Delta deal was found by Cheapflights users on 9/14. 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.
Mon 10/276:17 pmORF - PNS
1 stop5h 57mDelta
Sat 11/111:44 amPNS - ORF
1 stop4h 28mDelta
Deal found 9/14$257
This Delta deal was found by Cheapflights users on 9/12. 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 10/35:55 pmORF - PNS
1 stop6h 13mDelta
Mon 10/66:09 pmPNS - ORF
1 stop5h 11mDelta
Deal found 9/12$263

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 September 14, 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 2/18

6:00 am-11:07 am

1 stop6h 07m

Pensacola

Thu 2/26

9:25 am-2:00 pm

1 stop3h 35m

$241

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Wed 10/1

9:56 am-4:52 pm

2 stops7h 56m

Pensacola

Thu 10/2

3:57 pm-11:00 pm

1 stop6h 03m

$246

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sat 9/27

5:20 am-3:39 pm

1 stop11h 19m

Pensacola

Wed 10/1

4:44 pm-10:48 pm

1 stop5h 04m

$248

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Fri 10/31

5:24 am-3:31 pm

1 stop11h 07m

Pensacola

Tue 11/11

4:41 pm-11:40 pm

1 stop5h 59m

$255

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Mon 10/27

6:17 pm-11:14 pm

1 stop5h 57m

Pensacola

Sat 11/1

11:44 am-5:12 pm

1 stop4h 28m

$257

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Mon 11/10

5:46 am-11:11 am

2 stops6h 25m

Pensacola

Thu 11/13

5:24 am-12:28 pm

1 stop6h 04m

$262

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Fri 10/3

5:55 pm-11:08 pm

1 stop6h 13m

Pensacola

Mon 10/6

6:09 pm-12:20 am

1 stop5h 11m

$263

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Fri 10/3

7:00 am-2:55 pm

1 stop8h 55m

Pensacola

Sun 10/5

10:28 am-4:39 pm

1 stop5h 11m

$281

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Fri 10/31

2:10 pm-6:40 pm

1 stop5h 30m

Pensacola

Tue 11/11

6:00 am-2:43 pm

2 stops7h 43m

$287

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sat 9/27

5:20 am-3:39 pm

1 stop11h 19m

Pensacola

Wed 10/1

4:44 pm-4:12 pm

2 stops22h 28m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

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 September 12, 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, September is the cheapest month in which you can book a flight from Chesapeake to Pensacola (average of $303). Flying from Chesapeake to Pensacola in March is currently the most expensive (average of $415). 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 September 14, 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.

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 September 14, 2025.
Get a feel of what it's like to fly with Southwest, Breeze Airways, and Delta 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.
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Breeze Airways
8.0
Very good
205 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,956 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,016 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chesapeake to Pensacola?

    For as low as $241, Delta can have you in Pensacola from Chesapeake in 6h 07m. There are 770 mi between Chesapeake and Pensacola. Both multi-stop and nonstop flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $110. Delta flights start at $110 while deals on Breeze Airways start at $112 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 $303). Flying from Chesapeake to Pensacola in March is currently the most expensive (average of $415). 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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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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$140Average$206FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$154Average$326FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$228Average$432FlexibilityNo cancel feeOn-time71%
DeltaCheapest$256Average$422FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$296Average$447FlexibilityNo cancel feeOn-time63%

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