$68+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PNS
May 17 — May 241
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
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Best
Last-minute
One-way
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 April 17, 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 April 17, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:59 pm
ORF
- PNS
1 stop4h 39m
Spirit Airlines
Fri 5/16:36 am
PNS
- ORF
1 stop9h 28m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 6/19:12 pm
ORF
- PNS
1 stop19h 41m
Multiple Airlines
Sun 6/74:48 pm
PNS
- ORF
1 stop26h 29m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:02 pm
ORF
- PNS
1 stop22h 51m
Multiple Airlines
Fri 5/84:48 pm
PNS
- ORF
1 stop24h 41m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 4/12. 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.
Mon 6/19:12 pm
ORF
- PNS
1 stop19h 41m
Multiple Airlines
Tue 6/94:48 pm
PNS
- ORF
1 stop26h 52m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:24 pm
ORF
- PNS
1 stop19h 35m
Multiple Airlines
Wed 5/274:48 pm
PNS
- ORF
1 stop26h 29m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:49 pm
ORF
- PNS
1 stop20h 04m
Multiple Airlines
Wed 5/274:48 pm
PNS
- ORF
1 stop26h 29m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:24 pm
ORF
- PNS
1 stop19h 35m
Multiple Airlines
Thu 5/217:38 pm
PNS
- ORF
1 stop23h 39m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:24 pm
ORF
- PNS
1 stop19h 35m
Multiple Airlines
Fri 5/224:48 pm
PNS
- ORF
1 stop25h 01m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:34 pm
ORF
- PNS
1 stop20h 19m
Multiple Airlines
Wed 5/274:48 pm
PNS
- ORF
1 stop26h 29m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$185
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 April 17, 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 April 17, 2026.
This Breeze Airways deal was found by Cheapflights users on 4/16. 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.
Thu 10/16:00 am
ORF
- PNS
1 stop7h 05m
Breeze Airways
Sat 10/101:25 pm
PNS
- ORF
1 stop8h 04m
Breeze Airways
Deal found 4/16![Breeze Airways logo]()
$252
This Southwest deal was found by Cheapflights users on 4/15. 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 5/136:50 am
ORF
- PNS
2 stops8h 55m
Southwest
Wed 5/2010:10 am
PNS
- ORF
2 stops9h 40m
Southwest
Deal found 4/15![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 4/15. 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 8/95:15 am
ORF
- PNS
1 stop4h 02m
Delta
Sun 8/94:21 pm
PNS
- ORF
1 stop6h 23m
Delta
Deal found 4/15![Delta logo]()
$407
This United Airlines deal was found by Cheapflights users on 4/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
ORF
- PNS
1 stop8h 07m
United Airlines
Fri 7/3111:35 am
PNS
- ORF
2 stops11h 09m
United Airlines
Deal found 4/12![United Airlines logo]()
$456
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/412:15 pm
ORF
- PNS
2 stops10h 20m
Southwest
Tue 6/912:05 pm
PNS
- ORF
2 stops9h 30m
Southwest
Deal found 4/13![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 4/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:05 am
ORF
- PNS
2 stops10h 35m
Southwest
Tue 6/912:05 pm
PNS
- ORF
2 stops9h 30m
Southwest
Deal found 4/12![Southwest logo]()
$387
This United Airlines deal was found by Cheapflights users on 4/11. 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.
Thu 7/28:00 am
ORF
- PNS
1 stop6h 07m
United Airlines
Wed 7/82:09 pm
PNS
- ORF
1 stop6h 28m
United Airlines
Deal found 4/11![United Airlines logo]()
$487
This Southwest deal was found by Cheapflights users on 4/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:25 am
ORF
- PNS
2 stops7h 40m
Southwest
Thu 8/137:45 am
PNS
- ORF
2 stops9h 10m
Southwest
Deal found 4/11![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:25 am
ORF
- PNS
2 stops11h 20m
Southwest
Mon 8/107:45 am
PNS
- ORF
2 stops9h 10m
Southwest
Deal found 4/13![Southwest logo]()
$433
This Southwest deal was found by Cheapflights users on 4/16. 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 7/27:05 am
ORF
- PNS
2 stops10h 15m
Southwest
Mon 7/611:55 am
PNS
- ORF
2 stops9h 05m
Southwest
Deal found 4/16![Southwest logo]()
$437
Last-minute flights from Chesapeake to PensacolaDiscover last-minute flight deals from Chesapeake to Pensacola. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Pensacola. Data last updated April 17, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 4/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:59 pm
ORF
- PNS
1 stop4h 39m
Spirit Airlines
Fri 5/16:36 am
PNS
- ORF
1 stop9h 28m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:02 pm
ORF
- PNS
1 stop22h 51m
Multiple Airlines
Fri 5/84:48 pm
PNS
- ORF
1 stop24h 41m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:34 pm
ORF
- PNS
1 stop20h 19m
Multiple Airlines
Wed 5/274:48 pm
PNS
- ORF
1 stop26h 29m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:24 pm
ORF
- PNS
1 stop19h 35m
Multiple Airlines
Wed 5/274:48 pm
PNS
- ORF
1 stop26h 29m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:24 pm
ORF
- PNS
1 stop19h 35m
Multiple Airlines
Thu 5/217:38 pm
PNS
- ORF
1 stop23h 39m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:24 pm
ORF
- PNS
1 stop19h 35m
Multiple Airlines
Fri 5/224:48 pm
PNS
- ORF
1 stop25h 01m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:24 pm
ORF
- PNS
1 stop19h 35m
Multiple Airlines
Tue 5/264:48 pm
PNS
- ORF
2 stops17h 23m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:49 pm
ORF
- PNS
1 stop20h 04m
Multiple Airlines
Wed 5/274:48 pm
PNS
- ORF
1 stop26h 29m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:49 pm
ORF
- PNS
1 stop20h 04m
Multiple Airlines
Fri 5/224:48 pm
PNS
- ORF
1 stop25h 01m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$186
This CheapOair deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:44 pm
ORF
- PNS
1 stop21h 09m
Spirit Airlines
Fri 5/224:48 pm
PNS
- ORF
1 stop25h 01m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$190
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 April 17, 2026.
Search for one-way flight options from Chesapeake to Pensacola. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/11. 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.
Mon 5/46:02 pm
ORF
- PNS
1 stop22h 51m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$68
This Cheapflightsfares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:59 pm
ORF
- PNS
1 stop4h 39m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$72
This Cheapflightsfares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/263:15 pm
ORF
- PNS
1 stop7h 23m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/309:12 pm
ORF
- PNS
1 stop19h 41m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$90
This Cheapflightsfares deal was found by Cheapflights users on 4/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:59 pm
ORF
- PNS
1 stop4h 39m
Spirit Airlines
Deal found 4/11![Spirit Airlines logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1810:09 am
ORF
- PNS
1 stop7h 00m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$98
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:00 am
ORF
- PNS
1 stop7h 59m
Breeze Airways
Deal found 4/14![Breeze Airways logo]()
$103
This Trip.com deal was found by Cheapflights users on 4/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:13 am
ORF
- PNS
1 stop6h 23m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:59 pm
ORF
- PNS
1 stop4h 39m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$114
This CheapOair deal was found by Cheapflights users on 4/11. 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.
Sun 5/38:57 pm
ORF
- PNS
1 stop21h 06m
Spirit Airlines
Deal found 4/11![Spirit Airlines logo]()
$115
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 April 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $144 (Cheapflightsfares) |
One-way from | $68 (Kiwi.com) |
Popular in | November |
Cheapest in | September |
Average price | $392 |
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 April 17, 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
Thu 10/1
6:00 am-12:05 pm
1 stop7h 05m
Pensacola
Sat 10/10
1:25 pm-10:29 pm
1 stop8h 04m
$252
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Wed 5/13
6:50 am-2:45 pm
2 stops8h 55m
Pensacola
Wed 5/20
10:10 am-8:50 pm
2 stops9h 40m
$367
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Thu 6/4
12:15 pm-9:35 pm
2 stops10h 20m
Pensacola
Tue 6/9
12:05 pm-10:35 pm
2 stops9h 30m
$381
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Mon 6/1
6:05 am-3:40 pm
2 stops10h 35m
Pensacola
Tue 6/9
12:05 pm-10:35 pm
2 stops9h 30m
$387
Quickest round-trip
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Sun 8/9
5:15 am-8:17 am
1 stop4h 02m
Pensacola
Sun 8/9
4:21 pm-11:44 pm
1 stop6h 23m
$407
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Fri 8/7
6:25 am-1:05 pm
2 stops7h 40m
Pensacola
Thu 8/13
7:45 am-5:55 pm
2 stops9h 10m
$417
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Sat 8/8
6:25 am-4:45 pm
2 stops11h 20m
Pensacola
Mon 8/10
7:45 am-5:55 pm
2 stops9h 10m
$433
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Thu 7/2
7:05 am-4:20 pm
2 stops10h 15m
Pensacola
Mon 7/6
11:55 am-10:00 pm
2 stops9h 05m
$437
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Wed 7/1
6:00 am-1:07 pm
1 stop8h 07m
Pensacola
Fri 7/31
11:35 am-11:44 pm
2 stops11h 09m
$456
NorfolkPensacola
ORF - PNS
ORFPNS
Norfolk
Thu 7/2
8:00 am-1:07 pm
1 stop6h 07m
Pensacola
Wed 7/8
2:09 pm-9:37 pm
1 stop6h 28m
$487
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 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 April 10, 2026.
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 78 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 April 17, 2026.
Get a feel of what it's like to fly with Delta,American Airlines, andSpirit 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
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Food
7.2
Overall
7.9
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Food
7.2
Overall
7.9
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Food
7.2
Overall
7.9
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Food
7.2
Overall
7.9
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
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.
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Book flights to Pensacola if you plan to visit one of these locationsGulf Breeze
Navarre
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Perdido Key
Warrington
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$75 | Average$242 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$216 | Average$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$236 | Average$406 | FlexibilityNo cancel fee | On-timeN/A |