$53+ Cheap flights from Chesapeake, VA to Orlando (ORL)
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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Aug 15 — Aug 221
Round-trip
1 adult, Economy
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Find cheap flights from Chesapeake to Orlando 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.Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in February or August, booked 90 days in advance, depart on a Sunday or Monday and return on a Thursday
Cheap flight deals from Chesapeake to Orlando
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Best
Last-minute
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Cheapest flights from Chesapeake to OrlandoExplore the most affordable flight options available from Chesapeake to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2026.
Explore the most affordable flight options available from Chesapeake to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2026.
This Priceline deal was found by Cheapflights users on 7/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:00 am
ORF
- MCO
Nonstop2h 16m
Multiple Airlines
Tue 11/103:12 pm
MCO
- ORF
Nonstop2h 03m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$156
This Frontier deal was found by Cheapflights users on 7/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Thu 8/136:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 7/13![Frontier logo]()
$158
This Frontier deal was found by Cheapflights users on 7/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Mon 8/106:48 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 7/13![Frontier logo]()
$159
This Frontier deal was found by Cheapflights users on 7/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Wed 8/192:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 7/15![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Tue 8/49:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Fri 8/77:45 am
MCO
- ORF
1 stop27h 36m
Frontier
Deal found 7/13![Frontier logo]()
$162
This Priceline deal was found by Cheapflights users on 7/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:10 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Sat 11/143:12 pm
MCO
- ORF
Nonstop2h 03m
Frontier
Deal found 7/12![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 8/1012:10 pm
ORF
- MCO
1 stop7h 47m
Frontier
Mon 8/176:48 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 7/13![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 8/89:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Sat 8/155:24 pm
MCO
- ORF
1 stop17h 51m
Frontier
Deal found 7/12![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 10/312:57 pm
ORF
- MCO
1 stop9h 13m
Frontier
Sat 10/103:27 pm
MCO
- ORF
Nonstop2h 03m
Frontier
Deal found 7/13![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 7/11. 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.
Thu 8/612:10 pm
ORF
- MCO
1 stop7h 47m
Frontier
Sun 8/95:24 pm
MCO
- ORF
1 stop17h 51m
Frontier
Deal found 7/11![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 7/11. 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 8/1011:25 am
ORF
- SFB
1 stop11h 41m
Multiple Airlines
Mon 8/179:04 pm
SFB
- ORF
2 stops39h 21m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 7/15. 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.
Wed 8/1210:31 pm
ORF
- SFB
1 stop13h 00m
Multiple Airlines
Wed 8/191:21 pm
SFB
- ORF
2 stops45h 58m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$388
Best flights from Chesapeake to OrlandoDiscover carefully curated flight deals from Chesapeake to Orlando that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 16, 2026.
Discover carefully curated flight deals from Chesapeake to Orlando that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 16, 2026.
This Southwest deal was found by Cheapflights users on 7/12. 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.
Wed 11/49:55 am
ORF
- MCO
Nonstop2h 10m
Southwest
Tue 11/107:35 am
MCO
- ORF
1 stop5h 50m
Southwest
Deal found 7/12![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 7/15. 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.
Wed 10/288:10 am
ORF
- MCO
1 stop5h 21m
Delta
Thu 11/53:40 pm
MCO
- ORF
1 stop5h 33m
Delta
Deal found 7/15![Delta logo]()
$247
This Breeze Airways deal was found by Cheapflights users on 7/15. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Tue 12/812:57 pm
MCO
- ORF
Nonstop2h 07m
Breeze Airways
Deal found 7/15![Breeze Airways logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 7/15. 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.
Wed 8/1210:31 pm
ORF
- SFB
1 stop13h 00m
Multiple Airlines
Wed 8/191:21 pm
SFB
- ORF
2 stops45h 58m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 7/15. 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.
Thu 10/152:10 pm
ORF
- MCO
1 stop6h 25m
Southwest
Tue 10/203:45 pm
MCO
- ORF
2 stops6h 20m
Southwest
Deal found 7/15![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:05 pm
ORF
- MCO
1 stop4h 50m
Delta
Fri 12/116:15 am
MCO
- ORF
1 stop5h 18m
Delta
Deal found 7/12![Delta logo]()
$287
This Breeze Airways deal was found by Cheapflights users on 7/14. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:00 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Fri 12/1110:07 am
MCO
- ORF
1 stop9h 16m
Breeze Airways
Deal found 7/14![Breeze Airways logo]()
$321
This Southwest deal was found by Cheapflights users on 7/16. 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.
Fri 11/63:25 pm
ORF
- MCO
2 stops9h 30m
Southwest
Tue 11/107:35 am
MCO
- ORF
1 stop5h 50m
Southwest
Deal found 7/16![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 7/13. 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.
Fri 9/181:55 pm
ORF
- MCO
1 stop5h 15m
Southwest
Wed 9/2310:40 am
MCO
- ORF
2 stops6h 40m
Southwest
Deal found 7/13![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 7/13. 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.
Fri 9/181:55 pm
ORF
- MCO
2 stops6h 10m
Southwest
Mon 9/219:05 am
MCO
- ORF
2 stops8h 50m
Southwest
Deal found 7/13![Southwest logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 10/212:57 pm
ORF
- SFB
2 stops29h 22m
Multiple Airlines
Sun 10/116:09 pm
SFB
- ORF
1 stop16h 33m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 7/16. 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.
Mon 11/301:30 pm
ORF
- MCO
1 stop6h 05m
Southwest
Sat 12/55:15 pm
MCO
- ORF
Nonstop2h 00m
Southwest
Deal found 7/16![Southwest logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:25 am
ORF
- SFB
1 stop12h 02m
Multiple Airlines
Fri 8/712:54 pm
SFB
- ORF
2 stops46h 21m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$438
This Southwest deal was found by Cheapflights users on 7/15. 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.
Thu 10/2212:10 pm
ORF
- MCO
2 stops8h 40m
Southwest
Sun 10/257:40 am
MCO
- ORF
1 stop4h 15m
Southwest
Deal found 7/15![Southwest logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:00 am
ORF
- SFB
2 stops16h 45m
Multiple Airlines
Thu 8/139:02 am
SFB
- ORF
1 stop25h 38m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Wed 7/2210:31 pm
ORF
- SFB
1 stop13h 05m
Multiple Airlines
Mon 7/271:57 pm
SFB
- ORF
2 stops23h 33m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$482
This Kiwi.com deal was found by Cheapflights users on 7/15. 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.
Wed 7/2210:31 pm
ORF
- SFB
1 stop13h 05m
Multiple Airlines
Wed 7/297:40 pm
SFB
- ORF
2 stops39h 35m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$537
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Wed 8/510:31 pm
ORF
- SFB
1 stop13h 00m
Multiple Airlines
Sun 8/99:24 pm
SFB
- ORF
2 stops25h 44m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$550
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Fri 7/3111:25 am
ORF
- SFB
1 stop12h 02m
Multiple Airlines
Sun 8/28:59 am
SFB
- ORF
2 stops23h 54m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$823
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Wed 8/1210:31 pm
ORF
- SFB
1 stop13h 00m
Multiple Airlines
Sun 8/166:10 am
SFB
- ORF
2 stops11h 03m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$824
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2910:31 pm
ORF
- SFB
1 stop12h 45m
Multiple Airlines
Sun 8/26:00 am
SFB
- ORF
2 stops11h 13m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$940
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 7/2411:25 am
ORF
- SFB
1 stop12h 02m
Multiple Airlines
Sun 7/268:59 am
SFB
- ORF
2 stops23h 54m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$985
Last-minute flights from Chesapeake to OrlandoDiscover last-minute flight deals from Chesapeake to Orlando. Data last updated July 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Orlando. Data last updated July 16, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:25 am
ORF
- SFB
1 stop12h 02m
Multiple Airlines
Fri 8/712:54 pm
SFB
- ORF
2 stops46h 21m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$438
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Tue 8/49:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Fri 8/77:45 am
MCO
- ORF
1 stop27h 36m
Frontier
Deal found 7/13![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Tue 8/412:10 pm
ORF
- MCO
1 stop21h 25m
Frontier
Sat 8/86:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 7/13![Frontier logo]()
$163
This Frontier deal was found by Cheapflights users on 7/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/49:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Tue 8/116:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 7/13![Frontier logo]()
$164
This Frontier deal was found by Cheapflights users on 7/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Mon 8/106:48 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 7/13![Frontier logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 7/11. 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.
Thu 8/612:10 pm
ORF
- MCO
1 stop7h 47m
Frontier
Sun 8/95:24 pm
MCO
- ORF
1 stop17h 51m
Frontier
Deal found 7/11![Frontier logo]()
$167
This Frontier deal was found by Cheapflights users on 7/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Thu 8/136:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 7/13![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 8/89:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Sat 8/155:24 pm
MCO
- ORF
1 stop17h 51m
Frontier
Deal found 7/12![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:00 am
ORF
- SFB
2 stops16h 45m
Multiple Airlines
Thu 8/139:02 am
SFB
- ORF
1 stop25h 38m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 7/15. 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.
Wed 8/1212:10 pm
ORF
- MCO
1 stop10h 05m
Frontier
Fri 8/145:24 pm
MCO
- ORF
1 stop17h 57m
Frontier
Deal found 7/15![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 7/15. 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.
Wed 8/1210:31 pm
ORF
- SFB
1 stop13h 00m
Multiple Airlines
Wed 8/191:21 pm
SFB
- ORF
2 stops45h 58m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$388
This Frontier deal was found by Cheapflights users on 7/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Wed 8/192:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 7/15![Frontier logo]()
$161
One-way flights from Chesapeake to OrlandoSearch for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated July 16, 2026.
Search for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated July 16, 2026.
This Frontier deal was found by Cheapflights users on 7/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:10 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 7/11![Frontier logo]()
$53
This Frontier deal was found by Cheapflights users on 7/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:10 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 7/11![Frontier logo]()
$54
This Frontier deal was found by Cheapflights users on 7/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Deal found 7/11![Frontier logo]()
$55
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 1/116:00 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Deal found 7/13![Breeze Airways logo]()
$58
This Super.com deal was found by Cheapflights users on 7/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:10 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 7/11![Frontier logo]()
$59
This Frontier deal was found by Cheapflights users on 7/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Deal found 7/11![Frontier logo]()
$60
This Frontier deal was found by Cheapflights users on 7/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Deal found 7/11![Frontier logo]()
$61
This Kiwi.com deal was found by Cheapflights users on 7/12. 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.
Tue 10/136:25 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 7/12![Frontier logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 1/106:00 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Deal found 7/13![Breeze Airways logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 7/11. 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.
Sat 10/316:10 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 7/11![Frontier logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:10 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 7/14![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:10 pm
ORF
- SFB
2 stops48h 27m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$139
Find flight deals from Chesapeake to Orlando
Keep the following information in mind while searching for Chesapeake to Orlando flight deals. Data was last updated July 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $156 (Priceline) |
One-way from | $53 (Frontier) |
Popular in | April |
Cheapest in | February |
Average price | $199 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chesapeake to Orlando 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 16, 2026.
Use the filters below to find and compare flights from Chesapeake to Orlando that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 11/4
9:55 am-12:05 pm
Nonstop2h 10m
Orlando
Tue 11/10
7:35 am-1:25 pm
1 stop5h 50m
$242
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 10/28
8:10 am-1:31 pm
1 stop5h 21m
Orlando
Thu 11/5
3:40 pm-9:13 pm
1 stop5h 33m
$247
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Thu 10/15
2:10 pm-8:35 pm
1 stop6h 25m
Orlando
Tue 10/20
3:45 pm-10:05 pm
2 stops6h 20m
$252
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Mon 12/7
6:05 pm-10:55 pm
1 stop4h 50m
Orlando
Fri 12/11
6:15 am-11:33 am
1 stop5h 18m
$287
Quickest round-trip
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Thu 12/3
6:00 am-8:16 am
Nonstop2h 16m
Orlando
Tue 12/8
12:57 pm-3:04 pm
Nonstop2h 07m
$288
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Fri 11/6
3:25 pm-12:55 am
2 stops9h 30m
Orlando
Tue 11/10
7:35 am-1:25 pm
1 stop5h 50m
$292
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Fri 9/18
1:55 pm-7:10 pm
1 stop5h 15m
Orlando
Wed 9/23
10:40 am-5:20 pm
2 stops6h 40m
$292
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Fri 9/18
1:55 pm-8:05 pm
2 stops6h 10m
Orlando
Mon 9/21
9:05 am-5:55 pm
2 stops8h 50m
$297
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Mon 11/30
1:30 pm-7:35 pm
1 stop6h 05m
Orlando
Sat 12/5
5:15 pm-7:15 pm
Nonstop2h 00m
$302
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Thu 10/22
12:10 pm-8:50 pm
2 stops8h 40m
Orlando
Sun 10/25
7:40 am-11:55 am
1 stop4h 15m
$313
Showing 1-10 of 42 resultsSorted by cheapest first
Best time to book a flight from Chesapeake to Orlando
Have a flexible travel schedule? Discover the best time to fly to Orlando from Chesapeake with our price prediction graph.
ORF-MCO
ORF-SFB
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 Orlando
C6E-ORL
ORF-MCO
ORF-SFB
What is the cheapest time of day to fly from C6E to ORL?
Find hourly flight availability from Chesapeake to Orlando. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 16, 2026.
It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 41% on the flight price compared to flying at noon, which is usually more expensive.
How much does it cost to fly round-trip from Chesapeake to Orlando?
What is the cheapest day to fly from Chesapeake to Orlando?
Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Orlando. Price data was last updated on July 11, 2026.
Travelers seeking maximum savings on their Chesapeake to Orlando flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Orlando
Get insights into the airlines that provide service to Orlando. 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 Orlando. Reviews last updated July 16, 2026.
Peruse reviews from past customers who have flown with Breeze Airways,Southwest, andDelta from Chesapeake to Orlando to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.3
Comfort
8.2
Overall
8.2
Food
6.7
Crew
8.8
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Overall
8.2
Food
6.7
Crew
8.8
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Overall
8.2
Food
6.7
Crew
8.8
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Overall
8.2
Food
6.7
Crew
8.8
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Overall
8.2
Food
6.7
Crew
8.8
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Overall
8.2
Food
6.7
Crew
8.8
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 Orlando. 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chesapeake to Orlando
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Complete your trip
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Search flights from Chesapeake to Orlando by cabin class
Find flights from Chesapeake to Orlando, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Orlando
Explore flights to Orlando departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 16, 2026.
Chesapeake and Orlando flights
Browse other Chesapeake and Orlando flight options. Last updated on July 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 8 airlines flying from Chesapeake to Orlando
Discover the top 8 airlines that operate flights from Chesapeake to Orlando. 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 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$152 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$289 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$98 | Average$210 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$101 | Average$306 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$103 | Average$249 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$108 | Average$246 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$344 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$337 | FlexibilityNo cancel fee | On-time69% |