$54+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Jul 16 — Jul 231
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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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 June 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 June 16, 2026.
This Super.com deal was found by Cheapflights users on 6/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Wed 8/266:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/12![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier 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
Sat 10/173:27 pm
MCO
- ORF
Nonstop2h 03m
Frontier
Deal found 6/12![Frontier logo]()
$123
This Frontier deal was found by Cheapflights users on 6/13. 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.
Mon 8/319:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Wed 9/26:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/13![Frontier logo]()
$128
This Super.com deal was found by Cheapflights users on 6/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Mon 8/316:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/15![Frontier logo]()
$132
This Priceline deal was found by Cheapflights users on 6/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:34 pm
ORF
- MCO
Nonstop2h 13m
Multiple Airlines
Thu 7/239:52 am
MCO
- ORF
Nonstop2h 18m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$135
This Frontier deal was found by Cheapflights users on 6/11. 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 8/209:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Tue 8/256:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/11![Frontier logo]()
$136
This Super.com deal was found by Cheapflights users on 6/11. 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.
Wed 7/229:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Tue 8/46:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/11![Frontier logo]()
$137
This Priceline deal was found by Cheapflights users on 6/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Wed 7/226:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/15![Frontier logo]()
$138
This Frontier deal was found by Cheapflights users on 6/15. 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.
Wed 7/159:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Tue 7/216:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/15![Frontier logo]()
$139
This Super.com deal was found by Cheapflights users on 6/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Tue 7/216:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/15![Frontier logo]()
$142
This Frontier deal was found by Cheapflights users on 6/15. 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.
Wed 7/159:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Wed 7/226:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/15![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Thu 7/96:00 am
ORF
- SFB
2 stops16h 02m
Multiple Airlines
Sun 7/128:59 am
SFB
- ORF
1 stop25h 41m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$425
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 June 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 June 16, 2026.
This Breeze Airways deal was found by Cheapflights users on 6/15. 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.
Sat 7/187:00 am
ORF
- MCO
Nonstop2h 20m
Breeze Airways
Wed 7/227:27 pm
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 6/15![Breeze Airways logo]()
$183
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 8/2212:25 pm
ORF
- MCO
1 stop7h 00m
Southwest
Wed 8/262:05 pm
MCO
- ORF
2 stops6h 45m
Southwest
Deal found 6/11![Southwest logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Thu 7/96:00 am
ORF
- SFB
2 stops16h 02m
Multiple Airlines
Sun 7/128:59 am
SFB
- ORF
1 stop25h 41m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$425
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 7/74:30 pm
ORF
- MCO
1 stop4h 15m
Southwest
Tue 7/143:10 pm
MCO
- ORF
2 stops7h 30m
Southwest
Deal found 6/12![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 6/13. 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.
Wed 9/96:15 am
ORF
- MCO
2 stops8h 00m
Southwest
Wed 9/94:10 pm
MCO
- ORF
1 stop4h 40m
Southwest
Deal found 6/13![Southwest logo]()
$262
This Breeze Airways deal was found by Cheapflights users on 6/14. 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.
Sat 9/59:06 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Mon 9/77:23 pm
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 6/14![Breeze Airways logo]()
$328
This Southwest deal was found by Cheapflights users on 6/13. 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 8/16:00 am
ORF
- MCO
1 stop5h 05m
Southwest
Tue 8/48:35 am
MCO
- ORF
2 stops7h 20m
Southwest
Deal found 6/13![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 6/15. 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 7/304:30 pm
ORF
- MCO
1 stop5h 45m
Southwest
Sun 8/97:10 am
MCO
- ORF
1 stop7h 20m
Southwest
Deal found 6/15![Southwest logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Wed 8/510:31 pm
ORF
- SFB
1 stop13h 00m
Multiple Airlines
Wed 8/121:26 pm
SFB
- ORF
2 stops45h 53m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$444
This Southwest deal was found by Cheapflights users on 6/11. 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 7/316:00 am
ORF
- MCO
1 stop5h 50m
Southwest
Sun 8/25:25 pm
MCO
- ORF
1 stop6h 00m
Southwest
Deal found 6/11![Southwest logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 7/107:20 am
ORF
- SFB
2 stops10h 57m
Multiple Airlines
Sun 7/128:59 am
SFB
- ORF
1 stop25h 41m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$449
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sun 7/266:20 am
ORF
- MCO
2 stops6h 15m
Southwest
Wed 7/2910:15 am
MCO
- ORF
1 stop4h 10m
Southwest
Deal found 6/11![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 6/11. 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.
Mon 7/207:05 am
ORF
- MCO
2 stops8h 25m
Southwest
Fri 7/249:55 pm
MCO
- ORF
1 stop11h 30m
Southwest
Deal found 6/11![Southwest logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Fri 7/311:25 am
ORF
- SFB
1 stop12h 02m
Multiple Airlines
Mon 7/69:06 am
SFB
- ORF
2 stops24h 14m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$507
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 7/110:31 pm
ORF
- SFB
1 stop13h 05m
Multiple Airlines
Mon 7/66:02 pm
SFB
- ORF
2 stops41h 13m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$509
This Southwest deal was found by Cheapflights users on 6/15. 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.
Sat 8/159:55 am
ORF
- MCO
2 stops7h 00m
Southwest
Mon 8/171:30 pm
MCO
- ORF
2 stops8h 05m
Southwest
Deal found 6/15![Southwest logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Tue 7/78:20 am
ORF
- SFB
2 stops25h 12m
Multiple Airlines
Sat 7/1112:19 pm
SFB
- ORF
1 stop25h 10m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$525
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 7/26:00 am
ORF
- SFB
2 stops16h 02m
Multiple Airlines
Sun 7/58:59 am
SFB
- ORF
1 stop25h 41m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Thu 9/37:00 am
ORF
- SFB
2 stops13h 01m
Multiple Airlines
Sun 9/610:29 am
SFB
- ORF
1 stop24h 11m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$561
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 7/29:43 am
ORF
- SFB
1 stop25h 56m
Multiple Airlines
Tue 7/712:47 pm
SFB
- ORF
2 stops20h 19m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$606
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Fri 6/2611:25 am
ORF
- SFB
1 stop12h 05m
Multiple Airlines
Sun 6/288:58 am
SFB
- ORF
2 stops7h 49m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$718
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 11/2011:22 am
ORF
- SFB
1 stop5h 40m
Multiple Airlines
Sat 11/2810:25 am
SFB
- ORF
2 stops11h 45m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$828
Last-minute flights from Chesapeake to OrlandoDiscover last-minute flight deals from Chesapeake to Orlando. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Orlando. Data last updated June 16, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 6/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Wed 7/156:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/15![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Thu 7/96:00 am
ORF
- SFB
2 stops16h 02m
Multiple Airlines
Sun 7/128:59 am
SFB
- ORF
1 stop25h 41m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 7/107:20 am
ORF
- SFB
2 stops10h 57m
Multiple Airlines
Sun 7/128:59 am
SFB
- ORF
1 stop25h 41m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$449
This Super.com deal was found by Cheapflights users on 6/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/119:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Wed 7/156:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/12![Frontier logo]()
$154
This Super.com deal was found by Cheapflights users on 6/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Tue 7/216:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/15![Frontier logo]()
$142
This Frontier deal was found by Cheapflights users on 6/15. 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.
Wed 7/159:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Tue 7/216:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/15![Frontier logo]()
$139
This Frontier deal was found by Cheapflights users on 6/15. 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.
Wed 7/159:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Wed 7/226:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/15![Frontier logo]()
$143
This Priceline deal was found by Cheapflights users on 6/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:34 pm
ORF
- MCO
Nonstop2h 13m
Multiple Airlines
Thu 7/239:52 am
MCO
- ORF
Nonstop2h 18m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$135
This Frontier deal was found by Cheapflights users on 6/15. 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.
Mon 7/209:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Thu 7/236:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/15![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 7/209:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Wed 7/225:20 am
MCO
- ORF
1 stop5h 55m
Frontier
Deal found 6/15![Frontier logo]()
$162
This Priceline deal was found by Cheapflights users on 6/14. 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.
Tue 7/219:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Wed 7/296:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/14![Frontier logo]()
$153
This Super.com deal was found by Cheapflights users on 6/11. 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.
Wed 7/229:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Tue 8/46:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/11![Frontier logo]()
$137
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 June 16, 2026.
Search for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
This Frontier deal was found by Cheapflights users on 6/11. 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 8/59:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/11![Frontier logo]()
$54
This Super.com deal was found by Cheapflights users on 6/15. 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 Super.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
Deal found 6/15![Frontier logo]()
$59
This Super.com deal was found by Cheapflights users on 6/12. 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 Super.com 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 6/12![Frontier logo]()
$64
This Frontier deal was found by Cheapflights users on 6/15. 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.
Wed 7/159:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/15![Frontier logo]()
$69
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 6/12![Frontier logo]()
$74
This Frontier deal was found by Cheapflights users on 6/13. 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 8/119:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/13![Frontier logo]()
$76
This Frontier deal was found by Cheapflights users on 6/15. 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 9/39:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 6/15![Frontier logo]()
$79
This Super.com deal was found by Cheapflights users on 6/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/229:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 6/12![Frontier logo]()
$81
This Frontier deal was found by Cheapflights users on 6/11. 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 8/69:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/11![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Wed 7/229:06 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Deal found 6/12![Breeze Airways logo]()
$83
This Frontier deal was found by Cheapflights users on 6/11. 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 13m
Frontier
Deal found 6/11![Frontier logo]()
$84
This Super.com deal was found by Cheapflights users on 6/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/15![Frontier logo]()
$88
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 June 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $107 (Super.com) |
One-way from | $54 (Frontier) |
Popular in | April |
Cheapest in | February |
Average price | $202 |
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 June 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
Sat 7/18
7:00 am-9:20 am
Nonstop2h 20m
Orlando
Wed 7/22
7:27 pm-9:45 pm
Nonstop2h 18m
$183
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 8/22
12:25 pm-7:25 pm
1 stop7h 00m
Orlando
Wed 8/26
2:05 pm-8:50 pm
2 stops6h 45m
$229
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Tue 7/7
4:30 pm-8:45 pm
1 stop4h 15m
Orlando
Tue 7/14
3:10 pm-10:40 pm
2 stops7h 30m
$262
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 9/9
6:15 am-2:15 pm
2 stops8h 00m
Orlando
Wed 9/9
4:10 pm-8:50 pm
1 stop4h 40m
$262
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 8/1
6:00 am-11:05 am
1 stop5h 05m
Orlando
Tue 8/4
8:35 am-3:55 pm
2 stops7h 20m
$297
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Thu 7/30
4:30 pm-10:15 pm
1 stop5h 45m
Orlando
Sun 8/9
7:10 am-2:30 pm
1 stop7h 20m
$327
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Fri 7/31
6:00 am-11:50 am
1 stop5h 50m
Orlando
Sun 8/2
5:25 pm-11:25 pm
1 stop6h 00m
$327
Quickest round-trip
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 9/5
9:06 am-11:22 am
Nonstop2h 16m
Orlando
Mon 9/7
7:23 pm-9:41 pm
Nonstop2h 18m
$328
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sun 7/26
6:20 am-12:35 pm
2 stops6h 15m
Orlando
Wed 7/29
10:15 am-2:25 pm
1 stop4h 10m
$329
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Mon 7/20
7:05 am-3:30 pm
2 stops8h 25m
Orlando
Fri 7/24
9:55 pm-9:25 am
1 stop11h 30m
$338
Showing 1-10 of 41 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 June 16, 2026.
It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 39% on the flight price compared to flying at noon, which is usually more expensive.
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 June 16, 2026.
The most flights from C6E to ORL are scheduled on a Tuesday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).
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 June 13, 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 June 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.
Overall
8.2
Comfort
8.2
Crew
8.8
Food
6.7
Boarding
8.3
Entertainment
6.6
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Comfort
8.2
Crew
8.8
Food
6.7
Boarding
8.3
Entertainment
6.6
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Comfort
8.2
Crew
8.8
Food
6.7
Boarding
8.3
Entertainment
6.6
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Comfort
8.2
Crew
8.8
Food
6.7
Boarding
8.3
Entertainment
6.6
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Comfort
8.2
Crew
8.8
Food
6.7
Boarding
8.3
Entertainment
6.6
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Comfort
8.2
Crew
8.8
Food
6.7
Boarding
8.3
Entertainment
6.6
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.
Browse thousands of different options on Cheapflights for your next trip
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 June 16, 2026.
Chesapeake and Orlando flights
Browse other Chesapeake and Orlando flight options. Last updated on June 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 June 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$57 | Average$140 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$292 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$98 | Average$220 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$99 | Average$302 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$103 | Average$247 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$106 | Average$242 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$446 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$158 | Average$339 | FlexibilityNo cancel fee | On-time71% |