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Pensacola

$83+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
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

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 December 15, 2025.

This Delta deal was found by Cheapflights users on 12/13. 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 12/266:15 pmORF - PNS
1 stop5h 58mDelta
Wed 12/315:31 pmPNS - ORF
1 stop5h 47mDelta
Deal found 12/13$518
This American Airlines deal was found by Cheapflights users on 12/13. 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.
Fri 12/266:07 pmORF - PNS
1 stop4h 03mAmerican Airlines
Wed 12/3111:00 amPNS - ORF
2 stops8h 15mAmerican Airlines
Deal found 12/13$562
This Delta deal was found by Cheapflights users on 12/13. 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.
Sun 12/286:23 amORF - PNS
1 stop4h 18mDelta
Thu 1/18:20 amPNS - ORF
1 stop5h 19mDelta
Deal found 12/13$609
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Wed 12/177:00 amORF - PNS
1 stop25h 31mBreeze Airways
Thu 12/181:14 pmPNS - ORF
1 stop8h 44mBreeze Airways
Deal found 12/13$633
This Delta deal was found by Cheapflights users on 12/13. 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.
Sat 12/275:13 pmORF - PNS
1 stop5h 34mDelta
Sun 1/45:31 pmPNS - ORF
1 stop5h 47mDelta
Deal found 12/13$634
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Sun 12/283:09 pmORF - PNS
2 stops28h 05mMultiple Airlines
Thu 1/11:14 pmPNS - ORF
1 stop8h 44mMultiple Airlines
Deal found 12/13$659
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Wed 12/177:00 amORF - PNS
1 stop25h 31mMultiple Airlines
Sun 12/217:09 pmPNS - ORF
2 stops22h 36mMultiple Airlines
Deal found 12/13$662
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Wed 12/177:00 amORF - PNS
1 stop25h 31mMultiple Airlines
Thu 12/187:09 pmPNS - ORF
2 stops22h 36mMultiple Airlines
Deal found 12/13$679
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Wed 12/177:00 amORF - PNS
1 stop25h 31mMultiple Airlines
Fri 12/193:35 pmPNS - ORF
2 stops19h 35mMultiple Airlines
Deal found 12/13$688
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:30 amORF - PNS
1 stop8h 01mUnited Airlines
Fri 12/262:33 pmPNS - ORF
2 stops8h 08mUnited Airlines
Deal found 12/14$702

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 December 15, 2025.

Most accurate provider

Gotogate
3 stars

Most trusted provider

Gotogate
3 stars

Round-trip from

$178
(Kiwi.com)

One-way from

$83
(Trip.com)

Popular in

November

Cheapest in

September

Average price

$482
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. 21% potential increase in price ($111 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 December 2025
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 December 15, 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

Fri 1/9

6:45 am-4:37 pm

1 stop10h 52m

Pensacola

Thu 1/15

4:03 pm-6:38 pm

1 stop25h 35m

$178

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Tue 2/24

7:31 pm-3:54 pm

1 stop21h 23m

Pensacola

Wed 3/4

5:59 pm-6:28 pm

1 stop23h 29m

$190

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Mon 1/5

3:01 pm-1:03 pm

1 stop23h 02m

Pensacola

Fri 1/9

5:33 pm-9:50 pm

1 stop27h 17m

$195

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 2/5

6:45 am-4:37 pm

1 stop10h 52m

Pensacola

Sun 2/8

4:03 pm-6:38 pm

1 stop25h 35m

$199

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Fri 1/9

6:45 am-4:37 pm

1 stop10h 52m

Pensacola

Sun 1/11

1:18 pm-10:26 pm

1 stop8h 08m

$206

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 1/15

6:45 am-4:37 pm

1 stop10h 52m

Pensacola

Mon 1/19

7:31 pm-1:31 pm

1 stop17h 00m

$232

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 1/15

6:45 am-4:37 pm

1 stop10h 52m

Pensacola

Sun 1/18

5:33 pm-6:38 pm

2 stops24h 05m

$248

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Tue 1/13

7:45 am-1:53 pm

1 stop7h 08m

Pensacola

Sun 1/18

8:00 am-1:57 pm

1 stop4h 57m

$293

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sat 1/17

6:45 am-4:37 pm

1 stop10h 52m

$95

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Wed 1/7

3:01 pm-7:35 am

2 stops17h 34m

$125

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 15 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.

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 December 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, 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 $243). 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 15, 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 December 15, 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
8.2
Very good
248 reviews

Comfort

8.2

Entertainment

6.7

Boarding

8.4

Food

6.7

Overall

8.2

Crew

8.8

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Breeze Airways
8.2
Very good
248 reviews
Breeze Airways
8.2
Very good
248 reviews

Comfort

8.2

Entertainment

6.7

Boarding

8.4

Food

6.7

Overall

8.2

Crew

8.8

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Delta
7.9
Good
8,008 reviews
Breeze Airways
8.2
Very good
248 reviews

Comfort

8.2

Entertainment

6.7

Boarding

8.4

Food

6.7

Overall

8.2

Crew

8.8

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
American Airlines
7.2
Good
11,048 reviews
Breeze Airways
8.2
Very good
248 reviews

Comfort

8.2

Entertainment

6.7

Boarding

8.4

Food

6.7

Overall

8.2

Crew

8.8

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Spirit Airlines
6.3
Okay
8,188 reviews
Breeze Airways
8.2
Very good
248 reviews

Comfort

8.2

Entertainment

6.7

Boarding

8.4

Food

6.7

Overall

8.2

Crew

8.8

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.

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 $178, Spirit Airlines can have you in Pensacola from Chesapeake in 10h 52m. 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 Breeze Airways, which is currently one of the cheapest options available, starting at $84. American Airlines flights start at $118 while deals on Delta start at $118 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 January is currently the most expensive (average of $243). 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 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$87Average$197FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$140Average$317FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$218Average$425FlexibilityNo cancel feeOn-time71%
DeltaCheapest$250Average$417FlexibilityNo cancel feeOn-timeN/A

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