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Pensacola

$77+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Pensacola are usually found in May or September, 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 July 29, 2025.

Round-trip from

$184
(CheapOair)

One-way from

$77
(Breeze Airways)

Popular in

December

Cheapest in

May

Average price

$361
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. 7% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This CheapOair deal was found by Cheapflights users on 7/29. 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.
Wed 9/35:30 amORF - PNS
1 stop5h 22mSpirit Airlines
Wed 9/104:44 pmPNS - ORF
1 stop5h 04mSpirit Airlines
Deal found 7/29$184
This Priceline deal was found by Cheapflights users on 7/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/17:00 amORF - PNS
1 stop4h 25mBreeze Airways
Thu 9/41:14 pmPNS - ORF
1 stop8h 44mBreeze Airways
Deal found 7/26$198
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/51:35 pmORF - PNS
1 stop6h 22mDelta
Wed 11/123:35 pmPNS - ORF
1 stop4h 51mDelta
Deal found 7/27$237
This American Airlines deal was found by Cheapflights users on 7/29. 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 9/39:30 amORF - PNS
2 stops8h 22mAmerican Airlines
Wed 9/103:57 pmPNS - ORF
1 stop6h 03mAmerican Airlines
Deal found 7/29$242
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Thu 9/410:30 amORF - PNS
2 stops12h 30mUnited Airlines
Mon 9/82:15 pmPNS - ORF
1 stop6h 37mUnited Airlines
Deal found 7/29$272
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Thu 8/79:05 amORF - PNS
1 stop10h 24mMultiple Airlines
Sat 8/97:24 pmPNS - ORF
1 stop11h 51mMultiple Airlines
Deal found 7/29$299

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 July 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

Wed 9/3

5:30 am-9:52 am

1 stop5h 22m

Pensacola

Wed 9/10

4:44 pm-10:48 pm

1 stop5h 04m

$184

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Mon 9/1

7:00 am-10:25 am

1 stop4h 25m

Pensacola

Thu 9/4

1:14 pm-10:58 pm

1 stop8h 44m

$198

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Wed 9/3

9:30 am-4:52 pm

2 stops8h 22m

Pensacola

Wed 9/10

3:57 pm-11:00 pm

1 stop6h 03m

$242

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 9/4

10:30 am-10:00 pm

2 stops12h 30m

Pensacola

Mon 9/8

2:15 pm-9:52 pm

1 stop6h 37m

$272

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 8/7

9:05 am-6:29 pm

1 stop10h 24m

Pensacola

Sat 8/9

7:24 pm-8:15 am

1 stop11h 51m

$299

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Mon 8/11

7:00 am-10:25 am

1 stop4h 25m

$77

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 8/21

5:30 am-3:57 pm

1 stop11h 27m

$101

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sun 8/10

9:05 am-6:29 pm

1 stop10h 24m

$131

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Sat 8/9

6:20 am-5:05 pm

2 stops11h 45m

$260

NorfolkPensacola

ORF - PNS

ORFPNS

Norfolk

Thu 9/25

6:30 am-1:15 pm

1 stop7h 45m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 July 25, 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 $417). 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 July 29, 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 July 29, 2025.
Get a feel of what it's like to fly with Southwest, Breeze Airways, and United 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.
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
190 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,040 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $77. Spirit Airlines flights start at $101 while deals on Southwest start at $260 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 $306). Flying from Chesapeake to Pensacola in March is currently the most expensive (average of $417). 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
Milton
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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$149Average$204FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$154Average$317FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$256Average$431FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$416FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$296Average$447FlexibilityNo cancel feeOn-time63%

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