$152+ Cheap flights from Chesapeake, VA to Pensacola (PNS)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
Dec 12 — Dec 191
Round-trip
1 adult, Economy
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Find cheap flights from Chesapeake to Pensacola with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chesapeake to Pensacola
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Cheapest flights from Chesapeake to PensacolaExplore 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 November 12, 2026.
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 November 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/86:00 am -
1 stop7h 40m
Wed 12/91:25 pm -
1 stop8h 04m
Deal found 11/10![Breeze Airways logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Wed 12/91:25 pm -
1 stop8h 04m
Deal found 11/10![Breeze Airways logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/86:00 am -
1 stop7h 40m
Mon 12/141:25 pm -
1 stop8h 18m
Deal found 11/10![Breeze Airways logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Tue 12/88:48 am -
1 stop5h 16m
Deal found 11/10![Breeze Airways logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Mon 12/141:25 pm -
1 stop8h 18m
Deal found 11/10![Breeze Airways logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/86:00 am -
1 stop7h 40m
Thu 12/1012:45 pm -
1 stop9h 11m
Deal found 11/10![Breeze Airways logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Thu 12/1012:45 pm -
1 stop9h 11m
Deal found 11/10![Breeze Airways logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Tue 12/158:48 am -
1 stop5h 16m
Deal found 11/10![Breeze Airways logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/86:00 am -
1 stop7h 40m
Tue 12/151:20 pm -
2 stops28h 11m
Deal found 11/10![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Tue 12/151:20 pm -
2 stops28h 11m
Deal found 11/10![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/97:00 am -
1 stop25h 38m
Mon 12/141:25 pm -
1 stop8h 18m
Deal found 11/10![Breeze Airways logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Thu 12/106:00 am -
1 stop7h 05m
Mon 12/141:25 pm -
1 stop8h 18m
Deal found 11/10![Breeze Airways logo]()
$256
Best flights from Chesapeake to PensacolaDiscover carefully curated flight deals from Chesapeake to Pensacola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 12, 2026.
Discover carefully curated flight deals from Chesapeake to Pensacola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 12, 2026.
This Breeze Airways deal was found by Cheapflights users on 11/11. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:00 am -
1 stop9h 40m
Sun 1/102:37 pm -
1 stop7h 19m
Deal found 11/11![Breeze Airways logo]()
$222
This Delta deal was found by Cheapflights users on 11/7. 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 12/512:10 pm -
1 stop6h 47m
Tue 12/85:44 pm -
1 stop3h 51m
Deal found 11/7![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 11/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/301:25 pm -
2 stops11h 00m
Tue 1/56:20 am -
2 stops7h 05m
Deal found 11/8![Southwest logo]()
$438
This United Airlines deal was found by Cheapflights users on 11/10. 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.
Sat 12/511:49 am -
2 stops11h 10m
Tue 12/152:12 pm -
2 stops8h 31m
Deal found 11/10![United Airlines logo]()
$468
This Breeze Airways deal was found by Cheapflights users on 11/9. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/56:00 am -
1 stop9h 40m
Wed 2/104:35 pm -
1 stop4h 55m
Deal found 11/9![Breeze Airways logo]()
$305
This Delta deal was found by Cheapflights users on 11/10. 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.
Tue 12/17:29 pm -
1 stop5h 10m
Sun 12/136:23 pm -
1 stop4h 43m
Deal found 11/10![Delta logo]()
$402
This Southwest deal was found by Cheapflights users on 11/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/291:25 pm -
2 stops11h 00m
Tue 1/56:20 am -
2 stops7h 05m
Deal found 11/8![Southwest logo]()
$463
This United Airlines deal was found by Cheapflights users on 11/10. 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.
Fri 1/810:30 am -
2 stops12h 04m
Tue 1/129:00 am -
2 stops12h 59m
Deal found 11/10![United Airlines logo]()
$503
This Delta deal was found by Cheapflights users on 11/10. 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 12/67:00 am -
1 stop6h 44m
Sun 12/66:23 pm -
1 stop4h 43m
Deal found 11/10![Delta logo]()
$467
This United Airlines deal was found by Cheapflights users on 11/11. 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.
Sat 12/1211:49 am -
2 stops11h 10m
Wed 12/1612:55 pm -
1 stop8h 50m
Deal found 11/11![United Airlines logo]()
$532
This Delta deal was found by Cheapflights users on 11/11. 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.
Thu 11/264:55 pm -
1 stop6h 09m
Mon 11/306:13 pm -
1 stop5h 35m
Deal found 11/11![Delta logo]()
$557
Last-minute flights from Chesapeake to PensacolaDiscover last-minute flight deals from Chesapeake to Pensacola. Data last updated November 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Pensacola. Data last updated November 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Wed 12/91:25 pm -
1 stop8h 04m
Deal found 11/10![Breeze Airways logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Tue 12/88:48 am -
1 stop5h 16m
Deal found 11/10![Breeze Airways logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Mon 12/141:25 pm -
1 stop8h 18m
Deal found 11/10![Breeze Airways logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Thu 12/1012:45 pm -
1 stop9h 11m
Deal found 11/10![Breeze Airways logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Tue 12/158:48 am -
1 stop5h 16m
Deal found 11/10![Breeze Airways logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mon 12/76:00 am -
1 stop7h 45m
Tue 12/151:20 pm -
2 stops28h 11m
Deal found 11/10![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/86:00 am -
1 stop7h 40m
Wed 12/91:25 pm -
1 stop8h 04m
Deal found 11/10![Breeze Airways logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/86:00 am -
1 stop7h 40m
Mon 12/141:25 pm -
1 stop8h 18m
Deal found 11/10![Breeze Airways logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/86:00 am -
1 stop7h 40m
Thu 12/1012:45 pm -
1 stop9h 11m
Deal found 11/10![Breeze Airways logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/86:00 am -
1 stop7h 40m
Tue 12/151:20 pm -
2 stops28h 11m
Deal found 11/10![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/97:00 am -
1 stop25h 38m
Mon 12/141:25 pm -
1 stop8h 18m
Deal found 11/10![Breeze Airways logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Thu 12/106:00 am -
1 stop7h 05m
Mon 12/141:25 pm -
1 stop8h 18m
Deal found 11/10![Breeze Airways logo]()
$256
One-way flights from Chesapeake to PensacolaSearch for one-way flight options from Chesapeake to Pensacola. Find affordable one-way fares based on user searches. Data last updated November 12, 2026.
Search for one-way flight options from Chesapeake to Pensacola. Find affordable one-way fares based on user searches. Data last updated November 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Fri 12/117:26 pm -
2 stops38h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:00 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Breeze Airways logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:16 pm -
2 stops38h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:08 pm -
2 stops16h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Breeze Airways logo]()
$172
This American Airlines deal was found by Cheapflights users on 11/12. 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.
Sat 12/123:24 pm -
1 stop6h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![American Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 11/9. 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.
Thu 12/176:27 pm -
1 stop6h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![American Airlines logo]()
$189
This CheapOair deal was found by Cheapflights users on 11/11. 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.
Fri 12/1810:04 pm -
1 stop24h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Frontier logo]()
$196
This American Airlines deal was found by Cheapflights users on 11/11. 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 12/217:43 pm -
1 stop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![American Airlines logo]()
$199
This American Airlines deal was found by Cheapflights users on 11/11. 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 12/118:07 pm -
1 stop4h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![American Airlines logo]()
$214
This Southwest deal was found by Cheapflights users on 11/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/179:55 am -
2 stops11h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Southwest logo]()
$216
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 November 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $191 (Kiwi.com) |
One-way from | $152 (Kiwi.com) |
Popular in | December |
Cheapest in | April |
Average price | $442 |
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 7,457,451 searches. Data last updated November 12, 2026.
Use the filters below to find and compare flights from Chesapeake to Pensacola that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
NorfolkPensacola
ORF Norfolk - PNS Pensacola
ORFPNS
Norfolk
Fri 12/11
6:08 pm-9:50 am
2 stops16h 42m
Pensacola
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$172
Quickest round-trip
NorfolkPensacola
ORF Norfolk - PNS Pensacola
ORFPNS
Norfolk
Thu 12/17
6:27 pm-11:39 pm
1 stop6h 12m
Pensacola
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
NorfolkPensacola
ORF Norfolk - PNS Pensacola
ORFPNS
Norfolk
Fri 12/18
10:04 pm-9:06 pm
1 stop24h 02m
Pensacola
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$196
NorfolkPensacola
ORF Norfolk - PNS Pensacola
ORFPNS
Norfolk
Thu 12/17
9:55 am-8:35 pm
2 stops11h 40m
Pensacola
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$216
NorfolkPensacola
ORF Norfolk - PNS Pensacola
ORFPNS
Norfolk
Fri 1/8
6:00 am-2:40 pm
1 stop9h 40m
Pensacola
Sun 1/10
2:37 pm-10:56 pm
1 stop7h 19m
$222
NorfolkPensacola
ORF Norfolk - PNS Pensacola
ORFPNS
Norfolk
Thu 12/10
5:09 pm-9:50 am
3 stops41h 41m
Pensacola
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$235
NorfolkPensacola
ORF Norfolk - PNS Pensacola
ORFPNS
Norfolk
Fri 12/18
9:10 am-5:27 pm
3 stops33h 17m
Pensacola
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$251
NorfolkPensacola
ORF Norfolk - PNS Pensacola
ORFPNS
Norfolk
Fri 12/18
9:55 am-5:45 pm
2 stops8h 50m
Pensacola
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$255
NorfolkPensacola
ORF Norfolk - PNS Pensacola
ORFPNS
Norfolk
Mon 12/21
1:25 pm-11:25 pm
2 stops11h 00m
Pensacola
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$261
NorfolkPensacola
ORF Norfolk - PNS Pensacola
ORFPNS
Norfolk
Fri 12/11
12:10 pm-10:00 pm
2 stops10h 50m
Pensacola
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$266
Showing 1-10 of 20 resultsSorted by cheapest first
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.
ORF-PNS
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
C6E-PNS
ORF-PNS
How much does it cost to fly round-trip from Chesapeake to Pensacola?
Airfare is below average for this route at the moment.
Chesapeake to Pensacola flights typically cost between $371 and $497 in December.The cheapest round-trip price found within the last 5 days was $191 on Breeze Airways (Dec 8-Dec 9).
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 November 12, 2026.
Get a feel of what it's like to fly with Breeze Airways,Delta, andAmerican 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.
Boarding
8.4
Entertainment
6.8
Comfort
8.2
Overall
8.2
Food
6.7
Crew
8.8
Reviews
1 / 17
10.0
ExcellentJames,Oct 2026
RSW - RDU
Boarding
8.4
Entertainment
6.8
Comfort
8.2
Overall
8.2
Food
6.7
Crew
8.8
Reviews
1 / 17
10.0
ExcellentJames,Oct 2026
RSW - RDU
Boarding
8.4
Entertainment
6.8
Comfort
8.2
Overall
8.2
Food
6.7
Crew
8.8
Reviews
1 / 17
10.0
ExcellentJames,Oct 2026
RSW - RDU
Boarding
8.4
Entertainment
6.8
Comfort
8.2
Overall
8.2
Food
6.7
Crew
8.8
Reviews
1 / 17
10.0
ExcellentJames,Oct 2026
RSW - RDU
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.
Traveling to a place near Pensacola?
Book flights to Pensacola if you plan to visit one of these locationsAtmore
Navarre
Gulf Breeze
Foley
Evergreen
Navarre Beach
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Chesapeake and Pensacola flights
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Top 3 airlines flying from Chesapeake to Pensacola
Discover the top 3 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 7,457,451 searches. Data last updated November 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$207 | Average$371 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$269 | Average$460 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$502 | FlexibilityNo cancel fee | On-time71% |