$43+ 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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Apr 21 — Apr 281
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 May or February, booked 90 days in advance, depart on a Sunday or Thursday and return on a Thursday
Cheap flight deals from Chesapeake to Orlando
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Best
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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 March 22, 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 March 22, 2026.
This Frontier deal was found by Cheapflights users on 3/19. 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 4/106:24 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Fri 4/173:22 pm
MCO
- ORF
Nonstop2h 05m
Frontier
Deal found 3/19![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 3/236:45 am
ORF
- MCO
Nonstop2h 06m
Multiple Airlines
Thu 3/263:44 pm
MCO
- ORF
Nonstop2h 04m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 6/69:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Wed 6/179:15 am
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 3/17![Frontier logo]()
$87
This Frontier deal was found by Cheapflights users on 3/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:02 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Thu 5/76:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 3/22![Frontier logo]()
$88
This Frontier deal was found by Cheapflights users on 3/18. 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 5/27:16 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Sat 5/94:23 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 3/18![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 3/213:26 pm
ORF
- MCO
Nonstop2h 15m
Frontier
Sat 3/2812:24 pm
MCO
- ORF
Nonstop2h 07m
Frontier
Deal found 3/18![Frontier logo]()
$92
This Frontier deal was found by Cheapflights users on 3/17. 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 5/119:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Thu 5/216:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 3/17![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/233:15 pm
ORF
- MCO
Nonstop2h 07m
Multiple Airlines
Sun 4/267:00 am
MCO
- ORF
Nonstop2h 05m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$94
This Frontier deal was found by Cheapflights users on 3/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Thu 5/216:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 3/20![Frontier logo]()
$95
This CheapOair deal was found by Cheapflights users on 3/17. 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.
Tue 4/146:45 am
ORF
- MCO
Nonstop2h 06m
Multiple Airlines
Fri 4/173:22 pm
MCO
- ORF
Nonstop2h 05m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$96
This Frontier deal was found by Cheapflights users on 3/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Mon 6/16:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 3/20![Frontier logo]()
$98
This CheapOair deal was found by Cheapflights users on 3/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/193:15 pm
ORF
- MCO
Nonstop2h 07m
Multiple Airlines
Fri 4/2411:10 am
MCO
- ORF
Nonstop2h 04m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$100
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 March 22, 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 March 22, 2026.
This Breeze Airways deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:24 pm
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Sat 5/237:27 pm
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 3/17![Breeze Airways logo]()
$148
This Southwest deal was found by Cheapflights users on 3/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:25 am
ORF
- MCO
Nonstop2h 05m
Southwest
Sat 5/237:20 pm
MCO
- ORF
Nonstop2h 00m
Southwest
Deal found 3/21![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 3/17. 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 4/185:30 pm
ORF
- MCO
1 stop4h 32m
Delta
Sat 4/255:30 am
MCO
- ORF
1 stop4h 35m
Delta
Deal found 3/17![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 3/17. 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 5/196:15 am
ORF
- MCO
2 stops9h 43m
United Airlines
Sun 5/243:09 pm
MCO
- ORF
2 stops9h 32m
United Airlines
Deal found 3/17![United Airlines logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:31 pm
ORF
- SFB
1 stop22h 16m
Multiple Airlines
Fri 5/86:39 pm
SFB
- ORF
2 stops40h 32m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 3/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:20 pm
ORF
- MCO
1 stop4h 40m
Southwest
Wed 5/277:20 am
MCO
- ORF
1 stop4h 35m
Southwest
Deal found 3/21![Southwest logo]()
$217
This Breeze Airways deal was found by Cheapflights users on 3/17. 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.
Sun 7/57:00 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Sat 7/1110:06 am
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 3/17![Breeze Airways logo]()
$228
This Southwest deal was found by Cheapflights users on 3/18. 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.
Sun 4/198:35 pm
ORF
- MCO
1 stop4h 25m
Southwest
Thu 4/232:20 pm
MCO
- ORF
2 stops7h 40m
Southwest
Deal found 3/18![Southwest logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/1510:31 pm
ORF
- SFB
1 stop22h 16m
Multiple Airlines
Wed 4/224:29 pm
SFB
- ORF
2 stops51h 33m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 3/19. 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 4/175:25 pm
ORF
- MCO
1 stop6h 40m
Southwest
Fri 4/242:20 pm
MCO
- ORF
2 stops7h 40m
Southwest
Deal found 3/19![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 3/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:05 am
ORF
- MCO
2 stops7h 50m
Southwest
Fri 5/12:20 pm
MCO
- ORF
2 stops7h 40m
Southwest
Deal found 3/21![Southwest logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:31 pm
ORF
- SFB
1 stop19h 34m
Multiple Airlines
Sat 5/239:06 pm
SFB
- ORF
2 stops34h 25m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 7/110:31 pm
ORF
- SFB
1 stop13h 05m
Multiple Airlines
Sun 7/58:59 am
SFB
- ORF
1 stop25h 41m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 6/1010:31 pm
ORF
- SFB
1 stop12h 52m
Multiple Airlines
Sun 6/146:05 am
SFB
- ORF
2 stops26h 48m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1911:25 am
ORF
- SFB
1 stop12h 10m
Multiple Airlines
Mon 6/223:58 pm
SFB
- ORF
2 stops17h 22m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$438
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/1510:31 pm
ORF
- SFB
1 stop22h 16m
Multiple Airlines
Sun 4/191:41 pm
SFB
- ORF
2 stops8h 45m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/410:31 pm
ORF
- SFB
1 stop24h 42m
Multiple Airlines
Sun 4/127:17 pm
SFB
- ORF
2 stops42h 14m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$503
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 6/1310:31 pm
ORF
- SFB
1 stop12h 52m
Multiple Airlines
Sat 6/207:14 pm
SFB
- ORF
2 stops21h 33m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$600
Last-minute flights from Chesapeake to OrlandoDiscover last-minute flight deals from Chesapeake to Orlando. Data last updated March 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Orlando. Data last updated March 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 3/213:26 pm
ORF
- MCO
Nonstop2h 15m
Frontier
Sat 3/2812:24 pm
MCO
- ORF
Nonstop2h 07m
Frontier
Deal found 3/18![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 3/236:45 am
ORF
- MCO
Nonstop2h 06m
Multiple Airlines
Thu 3/263:44 pm
MCO
- ORF
Nonstop2h 04m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$85
This Frontier deal was found by Cheapflights users on 3/19. 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 4/106:24 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Fri 4/173:22 pm
MCO
- ORF
Nonstop2h 05m
Frontier
Deal found 3/19![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/106:24 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Sat 4/184:16 pm
MCO
- ORF
Nonstop2h 05m
Frontier
Deal found 3/17![Frontier logo]()
$87
This Priceline deal was found by Cheapflights users on 3/17. 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.
Fri 4/106:24 pm
ORF
- MCO
Nonstop2h 12m
Multiple Airlines
Sat 4/1810:15 am
MCO
- ORF
Nonstop2h 00m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/129:04 am
ORF
- MCO
Nonstop2h 09m
Frontier
Thu 4/165:15 am
MCO
- ORF
1 stop5h 17m
Frontier
Deal found 3/17![Frontier logo]()
$106
This CheapOair deal was found by Cheapflights users on 3/17. 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.
Tue 4/146:45 am
ORF
- MCO
Nonstop2h 06m
Multiple Airlines
Fri 4/173:22 pm
MCO
- ORF
Nonstop2h 05m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/1510:31 pm
ORF
- SFB
1 stop22h 16m
Multiple Airlines
Wed 4/224:29 pm
SFB
- ORF
2 stops51h 33m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$347
This Frontier deal was found by Cheapflights users on 3/17. 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 4/187:16 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Sat 4/254:16 pm
MCO
- ORF
Nonstop2h 05m
Frontier
Deal found 3/17![Frontier logo]()
$88
This Cheapflightsfares deal was found by Cheapflights users on 3/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/183:15 pm
ORF
- MCO
Nonstop2h 07m
Spirit Airlines
Sat 4/2512:22 pm
MCO
- ORF
Nonstop1h 58m
Spirit Airlines
Deal found 3/21![Spirit Airlines logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/233:15 pm
ORF
- MCO
Nonstop2h 07m
Multiple Airlines
Sun 4/267:00 am
MCO
- ORF
Nonstop2h 05m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$94
This CheapOair deal was found by Cheapflights users on 3/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/263:15 pm
ORF
- MCO
Nonstop2h 07m
Multiple Airlines
Sat 5/24:16 pm
MCO
- ORF
Nonstop2h 05m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$100
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 March 22, 2026.
Search for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated March 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/106:24 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Deal found 3/17![Frontier logo]()
$43
This Frontier deal was found by Cheapflights users on 3/17. 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 4/187:16 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 3/17![Frontier logo]()
$44
This Frontier deal was found by Cheapflights users on 3/18. 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 5/27:16 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 3/18![Frontier logo]()
$45
This Trip.com deal was found by Cheapflights users on 3/19. 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.
Fri 4/242:09 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Deal found 3/19![Frontier logo]()
$46
This Frontier deal was found by Cheapflights users on 3/19. 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 5/219:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 3/19![Frontier logo]()
$49
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
Tue 4/146:45 am
ORF
- MCO
Nonstop2h 06m
Spirit Airlines
Deal found 3/20![Spirit Airlines logo]()
$50
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:59 pm
ORF
- MCO
Nonstop2h 04m
Spirit Airlines
Deal found 3/20![Spirit Airlines logo]()
$51
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1912:32 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Deal found 3/21![Frontier logo]()
$52
This CheapOair deal was found by Cheapflights users on 3/19. 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 4/193:15 pm
ORF
- MCO
Nonstop2h 07m
Spirit Airlines
Deal found 3/19![Spirit Airlines logo]()
$57
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 8/39:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 3/19![Frontier logo]()
$58
This Trip.com deal was found by Cheapflights users on 3/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:06 pm
ORF
- MCO
1 stop7h 26m
Frontier
Deal found 3/21![Frontier logo]()
$60
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/810:31 pm
ORF
- SFB
1 stop22h 16m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$110
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 March 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $84 (Frontier) |
One-way from | $43 (Kiwi.com) |
Popular in | November |
Cheapest in | May |
Average price | $191 |
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 March 22, 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
Fri 5/15
5:24 pm-7:40 pm
Nonstop2h 16m
Orlando
Sat 5/23
7:27 pm-9:45 pm
Nonstop2h 18m
$148
Quickest round-trip
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 5/13
6:25 am-8:30 am
Nonstop2h 05m
Orlando
Sat 5/23
7:20 pm-9:20 pm
Nonstop2h 00m
$197
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 4/18
5:30 pm-10:02 pm
1 stop4h 32m
Orlando
Sat 4/25
5:30 am-10:05 am
1 stop4h 35m
$217
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 5/23
5:20 pm-10:00 pm
1 stop4h 40m
Orlando
Wed 5/27
7:20 am-11:55 am
1 stop4h 35m
$217
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sun 7/5
7:00 am-9:16 am
Nonstop2h 16m
Orlando
Sat 7/11
10:06 am-12:24 pm
Nonstop2h 18m
$228
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sun 4/19
8:35 pm-1:00 am
1 stop4h 25m
Orlando
Thu 4/23
2:20 pm-10:00 pm
2 stops7h 40m
$253
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Fri 4/17
5:25 pm-12:05 am
1 stop6h 40m
Orlando
Fri 4/24
2:20 pm-10:00 pm
2 stops7h 40m
$288
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Mon 4/27
6:05 am-1:55 pm
2 stops7h 50m
Orlando
Fri 5/1
2:20 pm-10:00 pm
2 stops7h 40m
$293
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Tue 5/19
6:15 am-3:58 pm
2 stops9h 43m
Orlando
Sun 5/24
3:09 pm-12:41 am
2 stops9h 32m
$298
NorfolkOrlando
ORF - SFB
ORFSFB
Norfolk
Sat 5/2
10:31 pm-8:47 pm
1 stop22h 16m
Orlando Sanford Intl
Fri 5/8
6:39 pm-11:11 am
2 stops40h 32m
$299
Showing 1-10 of 40 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
How far ahead should I book a flight from Chesapeake to Orlando?
Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Orlando. Price data was last updated on March 13, 2026.
To ensure you get the cheapest price possible for a flight from Chesapeake to Orlando, you should look to book at least 90 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chesapeake to Orlando?
Currently, September is the cheapest month in which you can book a flight from Chesapeake to Orlando (average of $42). Flying from Chesapeake to Orlando in December is currently the most expensive (average of $84). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 March 22, 2026.
It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 38% on the flight price compared to flying at noon, which is usually more expensive.
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 March 14, 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.
Weekly flight availability from Chesapeake to Orlando
Explore weekly flight availability from Chesapeake to Orlando. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 22, 2026.
The most flights from C6E to ORL are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Chesapeake to Orlando?
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 March 22, 2026.
Peruse reviews from past customers who have flown with Breeze Airways,Southwest, andAmerican Airlines 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.
Food
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Entertainment
6.6
Overall
8.1
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
Complete your trip to Orlando by adding a car rental and/or hotel reservation to your travel itinerary.
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 March 22, 2026.
Chesapeake and Orlando flights
Browse other Chesapeake and Orlando flight options. Last updated on March 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 9 airlines flying from Chesapeake to Orlando
Discover the top 9 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 March 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$41 | Average$130 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$58 | Average$145 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$78 | Average$160 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$88 | Average$302 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$91 | Average$222 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$293 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$100 | Average$247 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$437 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$162 | Average$333 | FlexibilityNo cancel fee | On-time71% |