$85+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
Aug 24 — Aug 311
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 July 25, 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 July 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/267:00 am
ORF
- PNS
1 stop7h 21m
Breeze Airways
Fri 8/284:10 pm
PNS
- ORF
1 stop4h 31m
Breeze Airways
Deal found 7/20![Breeze Airways logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/207:00 am
ORF
- PNS
1 stop8h 54m
Breeze Airways
Fri 8/281:17 pm
PNS
- ORF
1 stop8h 51m
Breeze Airways
Deal found 7/22![Breeze Airways logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/277:00 am
ORF
- PNS
1 stop8h 54m
Breeze Airways
Mon 8/311:17 pm
PNS
- ORF
1 stop8h 51m
Breeze Airways
Deal found 7/23![Breeze Airways logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/277:00 am
ORF
- PNS
1 stop8h 54m
Multiple Airlines
Mon 8/313:59 pm
PNS
- ORF
2 stops19h 26m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/267:00 am
ORF
- PNS
1 stop7h 21m
Multiple Airlines
Sat 8/298:26 am
PNS
- ORF
2 stops26h 59m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/207:00 am
ORF
- PNS
1 stop8h 54m
Multiple Airlines
Sat 8/228:26 am
PNS
- ORF
2 stops26h 59m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/267:00 am
ORF
- PNS
1 stop7h 21m
Multiple Airlines
Thu 8/273:59 pm
PNS
- ORF
1 stop23h 12m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/261:20 pm
ORF
- PNS
2 stops26h 34m
Multiple Airlines
Fri 8/284:10 pm
PNS
- ORF
1 stop4h 31m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/277:00 am
ORF
- PNS
1 stop8h 54m
Multiple Airlines
Sun 8/308:26 pm
PNS
- ORF
1 stop18h 45m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$248
This Breeze Airways deal was found by Cheapflights users on 7/23. 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.
Mon 9/216:00 am
ORF
- PNS
1 stop7h 45m
Breeze Airways
Thu 9/2412:45 pm
PNS
- ORF
1 stop9h 11m
Breeze Airways
Deal found 7/23![Breeze Airways logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/1012:10 pm
ORF
- PNS
2 stops28h 36m
Multiple Airlines
Tue 10/208:48 am
PNS
- ORF
1 stop7h 42m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$253
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 July 25, 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 July 25, 2026.
This Southwest deal was found by Cheapflights users on 7/20. 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.
Mon 8/246:00 am
ORF
- PNS
2 stops8h 05m
Southwest
Sat 8/297:05 am
PNS
- ORF
2 stops8h 50m
Southwest
Deal found 7/20![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 7/21. 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 9/126:00 am
ORF
- PNS
1 stop5h 39m
Delta
Sat 9/195:30 pm
PNS
- ORF
1 stop5h 50m
Delta
Deal found 7/21![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Wed 8/2610:41 am
ORF
- PNS
2 stops10h 09m
United Airlines
Thu 8/279:00 am
PNS
- ORF
2 stops13h 43m
United Airlines
Deal found 7/21![United Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 7/25. 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 10/139:55 am
ORF
- PNS
2 stops11h 15m
Southwest
Thu 10/1510:30 am
PNS
- ORF
2 stops9h 55m
Southwest
Deal found 7/25![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 7/20. 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.
Mon 8/1010:10 am
ORF
- PNS
2 stops9h 35m
Southwest
Tue 10/2012:35 pm
PNS
- ORF
2 stops8h 30m
Southwest
Deal found 7/20![Southwest logo]()
$351
This United Airlines deal was found by Cheapflights users on 7/22. 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 9/1010:49 am
ORF
- PNS
2 stops9h 57m
United Airlines
Wed 9/169:00 am
PNS
- ORF
2 stops12h 54m
United Airlines
Deal found 7/22![United Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Tue 8/2510:49 am
ORF
- PNS
2 stops12h 26m
United Airlines
Wed 8/269:00 am
PNS
- ORF
2 stops13h 02m
United Airlines
Deal found 7/21![United Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Wed 8/266:00 am
ORF
- PNS
1 stop8h 09m
United Airlines
Mon 8/312:20 pm
PNS
- ORF
2 stops8h 23m
United Airlines
Deal found 7/25![United Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 7/24. 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.
Fri 10/237:45 am
ORF
- PNS
2 stops9h 50m
Southwest
Sun 10/256:10 am
PNS
- ORF
2 stops11h 40m
Southwest
Deal found 7/24![Southwest logo]()
$441
Last-minute flights from Chesapeake to PensacolaDiscover last-minute flight deals from Chesapeake to Pensacola. Data last updated July 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Pensacola. Data last updated July 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/1012:10 pm
ORF
- PNS
2 stops28h 36m
Multiple Airlines
Tue 10/208:48 am
PNS
- ORF
1 stop7h 42m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/207:00 am
ORF
- PNS
1 stop8h 54m
Breeze Airways
Fri 8/281:17 pm
PNS
- ORF
1 stop8h 51m
Breeze Airways
Deal found 7/22![Breeze Airways logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/207:00 am
ORF
- PNS
1 stop8h 54m
Multiple Airlines
Sat 8/228:26 am
PNS
- ORF
2 stops26h 59m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/267:00 am
ORF
- PNS
1 stop7h 21m
Breeze Airways
Fri 8/284:10 pm
PNS
- ORF
1 stop4h 31m
Breeze Airways
Deal found 7/20![Breeze Airways logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/267:00 am
ORF
- PNS
1 stop7h 21m
Multiple Airlines
Sat 8/298:26 am
PNS
- ORF
2 stops26h 59m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/267:00 am
ORF
- PNS
1 stop7h 21m
Multiple Airlines
Thu 8/273:59 pm
PNS
- ORF
1 stop23h 12m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/261:20 pm
ORF
- PNS
2 stops26h 34m
Multiple Airlines
Fri 8/284:10 pm
PNS
- ORF
1 stop4h 31m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/277:00 am
ORF
- PNS
1 stop8h 54m
Breeze Airways
Mon 8/311:17 pm
PNS
- ORF
1 stop8h 51m
Breeze Airways
Deal found 7/23![Breeze Airways logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/277:00 am
ORF
- PNS
1 stop8h 54m
Multiple Airlines
Mon 8/313:59 pm
PNS
- ORF
2 stops19h 26m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/277:00 am
ORF
- PNS
1 stop8h 54m
Multiple Airlines
Sun 8/308:26 pm
PNS
- ORF
1 stop18h 45m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$248
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 July 25, 2026.
Search for one-way flight options from Chesapeake to Pensacola. Find affordable one-way fares based on user searches. Data last updated July 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/237:00 am
ORF
- PNS
1 stop8h 54m
Breeze Airways
Deal found 7/20![Breeze Airways logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/207:00 am
ORF
- PNS
1 stop8h 54m
Breeze Airways
Deal found 7/20![Breeze Airways logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/197:00 am
ORF
- PNS
1 stop7h 21m
Breeze Airways
Deal found 7/20![Breeze Airways logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/127:00 am
ORF
- PNS
1 stop7h 21m
Breeze Airways
Deal found 7/20![Breeze Airways logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/167:00 am
ORF
- PNS
1 stop8h 54m
Breeze Airways
Deal found 7/20![Breeze Airways logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/227:00 am
ORF
- PNS
1 stop8h 06m
Breeze Airways
Deal found 7/20![Breeze Airways logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/2412:04 pm
ORF
- PNS
1 stop4h 26m
Breeze Airways
Deal found 7/20![Breeze Airways logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/297:00 am
ORF
- PNS
1 stop8h 06m
Breeze Airways
Deal found 7/20![Breeze Airways logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/231:20 pm
ORF
- PNS
2 stops26h 54m
Frontier
Deal found 7/20![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/1712:10 pm
ORF
- PNS
2 stops21h 25m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/211:20 pm
ORF
- PNS
2 stops23h 49m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$127
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 July 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $199 (Kiwi.com) |
One-way from | $85 (Kiwi.com) |
Popular in | November |
Cheapest in | September |
Average price | $427 |
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 25, 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 - PNS
ORFPNS
Norfolk
Mon 8/24
6:00 am-1:05 pm
2 stops8h 05m
Pensacola
Sat 8/29
7:05 am-4:55 pm
2 stops8h 50m
$327
Quickest round-trip
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Sat 9/12
6:00 am-10:39 am
1 stop5h 39m
Pensacola
Sat 9/19
5:30 pm-12:20 am
1 stop5h 50m
$339
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Tue 10/13
9:55 am-8:10 pm
2 stops11h 15m
Pensacola
Thu 10/15
10:30 am-9:25 pm
2 stops9h 55m
$341
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Mon 8/10
10:10 am-6:45 pm
2 stops9h 35m
Pensacola
Tue 10/20
12:35 pm-10:05 pm
2 stops8h 30m
$351
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Wed 8/26
10:41 am-7:50 pm
2 stops10h 09m
Pensacola
Thu 8/27
9:00 am-11:43 pm
2 stops13h 43m
$407
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Thu 9/10
10:49 am-7:46 pm
2 stops9h 57m
Pensacola
Wed 9/16
9:00 am-10:54 pm
2 stops12h 54m
$407
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Tue 8/25
10:49 am-10:15 pm
2 stops12h 26m
Pensacola
Wed 8/26
9:00 am-11:02 pm
2 stops13h 02m
$407
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Wed 8/26
6:00 am-1:09 pm
1 stop8h 09m
Pensacola
Mon 8/31
2:20 pm-11:43 pm
2 stops8h 23m
$410
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Fri 10/23
7:45 am-4:35 pm
2 stops9h 50m
Pensacola
Sun 10/25
6:10 am-6:50 pm
2 stops11h 40m
$441
Cheapest one-way
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Sun 9/6
6:15 am-1:17 pm
2 stops8h 02m
$164
Showing 1-10 of 18 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 $339 and $538 in August.The cheapest round-trip price found within the last 5 days was $199 on Breeze Airways (Aug 26-Aug 28).
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 25, 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.
Overall
8.2
Boarding
8.3
Crew
8.8
Comfort
8.2
Food
6.7
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Boarding
8.3
Crew
8.8
Comfort
8.2
Food
6.7
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Boarding
8.3
Crew
8.8
Comfort
8.2
Food
6.7
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Boarding
8.3
Crew
8.8
Comfort
8.2
Food
6.7
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
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 locationsGulf Breeze
Navarre
Foley
Navarre Beach
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Chesapeake and Pensacola flights
Browse other Chesapeake and Pensacola flight options. Last updated on July 25, 2026.
Other flights to Pensacola
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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 2,558,603 searches. Data last updated July 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$154 | Average$285 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$236 | Average$430 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$286 | Average$439 | FlexibilityNo cancel fee | On-time71% |