$140+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
lug 9 — lug 161
Round-trip
1 adult, Economy
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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 giugno 9, 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 giugno 9, 2026.
This Breeze Airways deal was found by Cheapflights users on 6/6. 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.
lun 8/3112:04 pm
ORF
- PNS
1 stop4h 26m
Breeze Airways
ven 9/41:17 pm
PNS
- ORF
1 stop8h 31m
Breeze Airways
Deal found 6/6![Breeze Airways logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
gio 8/279:56 pm
ORF
- PNS
1 stop18h 34m
Multiple Airlines
lun 8/311:17 pm
PNS
- ORF
1 stop8h 51m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
mar 9/19:56 pm
ORF
- PNS
1 stop15h 13m
Multiple Airlines
sab 9/58:26 am
PNS
- ORF
1 stop11h 35m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 8/89:34 pm
ORF
- PNS
1 stop18h 20m
Multiple Airlines
sab 8/158:26 am
PNS
- ORF
1 stop11h 13m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
mar 7/286:12 pm
ORF
- PNS
2 stops14h 34m
Multiple Airlines
ven 7/314:11 pm
PNS
- ORF
1 stop27h 28m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 8/276:00 am
ORF
- PNS
1 stop26h 46m
Breeze Airways
lun 8/311:17 pm
PNS
- ORF
1 stop8h 51m
Breeze Airways
Deal found 6/8![Breeze Airways logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 8/119:34 pm
ORF
- PNS
1 stop15h 35m
Multiple Airlines
gio 8/2012:49 pm
PNS
- ORF
1 stop10h 04m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
sab 7/47:00 am
ORF
- PNS
1 stop6h 09m
Breeze Airways
ven 7/101:17 pm
PNS
- ORF
1 stop8h 51m
Breeze Airways
Deal found 6/4![Breeze Airways logo]()
$262
This CheapOair deal was found by Cheapflights users on 6/4. 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.
sab 7/48:08 pm
ORF
- PNS
1 stop20h 08m
Frontier
sab 7/117:26 pm
PNS
- ORF
1 stop24h 13m
Frontier
Deal found 6/4![Frontier logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 7/157:00 am
ORF
- PNS
1 stop7h 21m
Breeze Airways
ven 7/244:10 pm
PNS
- ORF
1 stop4h 31m
Breeze Airways
Deal found 6/7![Breeze Airways logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 7/159:34 pm
ORF
- PNS
1 stop18h 20m
Multiple Airlines
mar 7/214:41 pm
PNS
- ORF
1 stop26h 58m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$270
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 giugno 9, 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 giugno 9, 2026.
This Breeze Airways deal was found by Cheapflights users on 6/4. 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.
mer 7/17:00 am
ORF
- PNS
1 stop7h 21m
Breeze Airways
ven 7/311:17 pm
PNS
- ORF
1 stop8h 51m
Breeze Airways
Deal found 6/4![Breeze Airways logo]()
$340
This Delta deal was found by Cheapflights users on 6/4. 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.
ven 7/175:15 am
ORF
- PNS
1 stop4h 02m
Delta
ven 7/176:08 pm
PNS
- ORF
1 stop4h 36m
Delta
Deal found 6/4![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 6/6. 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.
sab 7/111:10 pm
ORF
- PNS
2 stops7h 00m
Southwest
ven 7/317:50 am
PNS
- ORF
2 stops9h 45m
Southwest
Deal found 6/6![Southwest logo]()
$423
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven 10/96:05 pm
ORF
- PNS
1 stop6h 22m
Delta
dom 10/116:00 am
PNS
- ORF
1 stop4h 33m
Delta
Deal found 6/8![Delta logo]()
$415
This Southwest deal was found by Cheapflights users on 6/8. 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.
ven 10/911:45 am
ORF
- PNS
1 stop6h 30m
Southwest
dom 10/112:40 pm
PNS
- ORF
2 stops8h 00m
Southwest
Deal found 6/8![Southwest logo]()
$509
This Delta deal was found by Cheapflights users on 6/7. 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.
ven 7/37:52 am
ORF
- PNS
1 stop6h 12m
Delta
dom 7/57:34 pm
PNS
- ORF
1 stop4h 11m
Delta
Deal found 6/7![Delta logo]()
$467
This Delta deal was found by Cheapflights users on 6/7. 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.
mar 6/238:00 am
ORF
- PNS
1 stop6h 04m
Delta
dom 7/57:34 pm
PNS
- ORF
1 stop4h 11m
Delta
Deal found 6/7![Delta logo]()
$533
This Southwest deal was found by Cheapflights users on 6/8. 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.
mer 6/2411:40 am
ORF
- PNS
2 stops9h 15m
Southwest
ven 6/2611:05 am
PNS
- ORF
2 stops9h 55m
Southwest
Deal found 6/8![Southwest logo]()
$587
Last-minute flights from Chesapeake to PensacolaDiscover last-minute flight deals from Chesapeake to Pensacola. Data last updated giugno 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Pensacola. Data last updated giugno 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
sab 7/47:00 am
ORF
- PNS
1 stop6h 09m
Breeze Airways
ven 7/101:17 pm
PNS
- ORF
1 stop8h 51m
Breeze Airways
Deal found 6/4![Breeze Airways logo]()
$262
This CheapOair deal was found by Cheapflights users on 6/4. 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.
sab 7/48:08 pm
ORF
- PNS
1 stop20h 08m
Frontier
sab 7/117:26 pm
PNS
- ORF
1 stop24h 13m
Frontier
Deal found 6/4![Frontier logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
sab 7/47:00 am
ORF
- PNS
1 stop6h 09m
Multiple Airlines
sab 7/1112:49 pm
PNS
- ORF
2 stops21h 26m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$288
This CheapOair deal was found by Cheapflights users on 6/5. 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.
lun 7/139:34 pm
ORF
- PNS
1 stop19h 12m
Frontier
mer 7/154:29 pm
PNS
- ORF
1 stop27h 10m
Frontier
Deal found 6/5![Frontier logo]()
$273
This CheapOair deal was found by Cheapflights users on 6/6. 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.
lun 7/139:34 pm
ORF
- PNS
1 stop19h 12m
Frontier
gio 7/164:11 pm
PNS
- ORF
1 stop27h 28m
Frontier
Deal found 6/6![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 7/146:12 pm
ORF
- PNS
2 stops14h 34m
Multiple Airlines
mer 7/224:29 pm
PNS
- ORF
1 stop27h 10m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 7/149:34 pm
ORF
- PNS
1 stop15h 35m
Multiple Airlines
lun 7/204:11 pm
PNS
- ORF
1 stop27h 28m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 7/157:00 am
ORF
- PNS
1 stop7h 21m
Breeze Airways
ven 7/244:10 pm
PNS
- ORF
1 stop4h 31m
Breeze Airways
Deal found 6/7![Breeze Airways logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 7/159:34 pm
ORF
- PNS
1 stop18h 20m
Multiple Airlines
mar 7/214:41 pm
PNS
- ORF
1 stop26h 58m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 7/159:34 pm
ORF
- PNS
1 stop18h 20m
Multiple Airlines
gio 7/238:26 pm
PNS
- ORF
1 stop23h 13m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
mar 7/286:12 pm
ORF
- PNS
2 stops14h 34m
Multiple Airlines
ven 7/314:11 pm
PNS
- ORF
1 stop27h 28m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$257
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 giugno 9, 2026.
Search for one-way flight options from Chesapeake to Pensacola. Find affordable one-way fares based on user searches. Data last updated giugno 9, 2026.
This CheapOair deal was found by Cheapflights users on 6/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 7/159:34 pm
ORF
- PNS
1 stop18h 40m
Frontier
Deal found 6/8![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
gio 7/212:21 pm
ORF
- PNS
2 stops48h 48m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$167
This American Airlines deal was found by Cheapflights users on 6/5. 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.
ven 7/37:59 pm
ORF
- PNS
1 stop5h 00m
American Airlines
Deal found 6/5![American Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 6/5. 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.
ven 7/312:15 pm
ORF
- PNS
2 stops10h 20m
Southwest
Deal found 6/5![Southwest logo]()
$183
This CheapOair deal was found by Cheapflights users on 6/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 7/59:34 pm
ORF
- PNS
1 stop18h 40m
Frontier
Deal found 6/8![Frontier logo]()
$195
This American Airlines deal was found by Cheapflights users on 6/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 7/26:00 am
ORF
- PNS
1 stop4h 56m
American Airlines
Deal found 6/8![American Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 6/247:00 am
ORF
- PNS
1 stop7h 21m
Breeze Airways
Deal found 6/8![Breeze Airways logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
sab 7/189:34 pm
ORF
- PNS
2 stops15h 35m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
mer 6/177:00 am
ORF
- PNS
1 stop7h 21m
Breeze Airways
Deal found 6/6![Breeze Airways logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 6/2312:21 pm
ORF
- PNS
2 stops22h 25m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 6/207:00 am
ORF
- PNS
1 stop7h 21m
Breeze Airways
Deal found 6/7![Breeze Airways logo]()
$235
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 giugno 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $229 (Breeze Airways) |
One-way from | $140 (CheapOair) |
Popular in | November |
Cheapest in | September |
Average price | $438 |
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 giugno 9, 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
mer 7/1
7:00 am-1:21 pm
1 stop7h 21m
Pensacola
ven 7/31
1:17 pm-11:08 pm
1 stop8h 51m
$340
Quickest round-trip
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
ven 7/17
5:15 am-8:17 am
1 stop4h 02m
Pensacola
ven 7/17
6:08 pm-11:44 pm
1 stop4h 36m
$407
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
ven 10/9
6:05 pm-11:27 pm
1 stop6h 22m
Pensacola
dom 10/11
6:00 am-11:33 am
1 stop4h 33m
$415
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
sab 7/11
1:10 pm-7:10 pm
2 stops7h 00m
Pensacola
ven 7/31
7:50 am-6:35 pm
2 stops9h 45m
$423
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
ven 7/3
7:52 am-1:04 pm
1 stop6h 12m
Pensacola
dom 7/5
7:34 pm-12:45 am
1 stop4h 11m
$467
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
ven 10/9
11:45 am-5:15 pm
1 stop6h 30m
Pensacola
dom 10/11
2:40 pm-11:40 pm
2 stops8h 00m
$509
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
mar 6/23
8:00 am-1:04 pm
1 stop6h 04m
Pensacola
dom 7/5
7:34 pm-12:45 am
1 stop4h 11m
$533
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
mer 6/24
11:40 am-7:55 pm
2 stops9h 15m
Pensacola
ven 6/26
11:05 am-10:00 pm
2 stops9h 55m
$587
Cheapest one-way
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
mer 7/15
9:34 pm-3:14 pm
1 stop18h 40m
$140
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
sab 7/18
9:34 pm-3:14 pm
1 stop18h 40m
$140
Showing 1-10 of 19 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?
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 giugno 9, 2026.
Get a feel of what it's like to fly with 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.
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - 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
Foley
Navarre Beach
Navarre
Perdido Key
Warrington
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Chesapeake and Pensacola flights
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Top 2 airlines flying from Chesapeake to Pensacola
Discover the top 2 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 giugno 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$236 | Average$419 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$251 | Average$434 | FlexibilityNo cancel fee | On-time71% |