$84+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Aug 29 — Sep 51
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 May, booked 86 days in advance, depart on a Sunday or Saturday 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 July 30, 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 30, 2026.
This Frontier deal was found by Cheapflights users on 7/28. 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 8/159:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Sun 8/232:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 7/28![Frontier logo]()
$158
This Priceline deal was found by Cheapflights users on 7/29. 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.
Thu 9/247:43 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Sun 9/274:44 pm
MCO
- ORF
Nonstop2h 04m
Frontier
Deal found 7/29![Frontier logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 8/205:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Sun 8/3010:03 am
MCO
- ORF
1 stop26h 22m
Frontier
Deal found 7/25![Frontier logo]()
$160
This Flightnetwork deal was found by Cheapflights users on 7/26. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:00 am
ORF
- MCO
Nonstop2h 12m
Multiple Airlines
Mon 8/242:03 pm
MCO
- ORF
Nonstop2h 08m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/251:20 pm
ORF
- MCO
1 stop5h 13m
Frontier
Tue 9/15:24 am
MCO
- ORF
1 stop7h 01m
Frontier
Deal found 7/28![Frontier logo]()
$162
This Frontier deal was found by Cheapflights users on 7/28. 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 8/285:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Sun 8/302:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 7/28![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/231:20 pm
ORF
- MCO
1 stop6h 40m
Frontier
Wed 8/265:24 am
MCO
- ORF
1 stop7h 01m
Frontier
Deal found 7/27![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 9/65:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Sun 9/136:50 am
MCO
- ORF
1 stop5h 39m
Frontier
Deal found 7/27![Frontier logo]()
$165
This Frontier deal was found by Cheapflights users on 7/26. 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 10/316:10 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Sat 11/73:12 pm
MCO
- ORF
Nonstop2h 03m
Frontier
Deal found 7/26![Frontier logo]()
$166
This Super.com deal was found by Cheapflights users on 7/26. 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 8/185:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Sun 8/232:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 7/26![Frontier logo]()
$167
This Priceline deal was found by Cheapflights users on 7/26. 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 8/179:53 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Sun 8/232:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 7/26![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 9/51:20 pm
ORF
- MCO
1 stop6h 40m
Frontier
Sat 9/124:44 pm
MCO
- ORF
Nonstop2h 04m
Frontier
Deal found 7/25![Frontier logo]()
$169
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 30, 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 30, 2026.
This Southwest deal was found by Cheapflights users on 7/24. 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 9/210:05 am
ORF
- MCO
Nonstop2h 10m
Southwest
Wed 9/99:00 am
MCO
- ORF
2 stops8h 20m
Southwest
Deal found 7/24![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 7/29. 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.
Tue 8/251:51 pm
ORF
- MCO
1 stop5h 57m
Delta
Tue 9/110:05 am
MCO
- ORF
1 stop7h 03m
Delta
Deal found 7/29![Delta logo]()
$227
This Breeze Airways deal was found by Cheapflights users on 7/29. 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 12/1112:57 pm
MCO
- ORF
Nonstop2h 07m
Breeze Airways
Deal found 7/29![Breeze Airways logo]()
$298
This United Airlines deal was found by Cheapflights users on 7/28. 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 9/296:15 am
ORF
- MCO
2 stops7h 57m
United Airlines
Mon 10/57:15 am
MCO
- ORF
1 stop8h 01m
United Airlines
Deal found 7/28![United Airlines logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 9/510:31 pm
ORF
- SFB
1 stop19h 58m
Multiple Airlines
Sat 9/126:17 pm
SFB
- ORF
2 stops25h 47m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 7/25. 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 8/1912:15 pm
ORF
- MCO
1 stop6h 45m
Southwest
Sat 8/296:25 am
MCO
- ORF
2 stops8h 35m
Southwest
Deal found 7/25![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 7/25. 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 8/229:55 am
ORF
- MCO
2 stops7h 00m
Southwest
Sat 8/297:10 am
MCO
- ORF
1 stop4h 35m
Southwest
Deal found 7/25![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 7/25. 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 10/247:55 am
ORF
- MCO
2 stops8h 10m
Southwest
Sat 10/317:40 am
MCO
- ORF
1 stop4h 15m
Southwest
Deal found 7/25![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 7/24. 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.
Fri 11/133:05 pm
ORF
- MCO
1 stop5h 31m
Delta
Tue 11/177:50 pm
MCO
- ORF
1 stop4h 24m
Delta
Deal found 7/24![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 7/29. 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 9/113:45 pm
ORF
- MCO
2 stops7h 10m
Southwest
Tue 9/159:00 am
MCO
- ORF
2 stops8h 20m
Southwest
Deal found 7/29![Southwest logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/166:00 am
ORF
- SFB
2 stops16h 56m
Multiple Airlines
Sun 8/2310:00 am
SFB
- ORF
1 stop24h 40m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$374
This Southwest deal was found by Cheapflights users on 7/28. 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 10/26:25 am
ORF
- MCO
1 stop5h 10m
Southwest
Mon 10/53:40 pm
MCO
- ORF
2 stops7h 55m
Southwest
Deal found 7/28![Southwest logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/177:20 am
ORF
- SFB
2 stops9h 21m
Multiple Airlines
Sun 8/2310:00 am
SFB
- ORF
1 stop24h 40m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 7/27. 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 9/76:00 am
ORF
- MCO
1 stop6h 20m
Southwest
Fri 9/119:30 am
MCO
- ORF
2 stops8h 25m
Southwest
Deal found 7/27![Southwest logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/209:43 am
ORF
- SFB
1 stop25h 23m
Multiple Airlines
Sun 8/2310:00 am
SFB
- ORF
1 stop24h 40m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 7/29. 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 12/23:05 pm
ORF
- MCO
2 stops8h 15m
Southwest
Fri 12/119:05 am
MCO
- ORF
2 stops8h 10m
Southwest
Deal found 7/29![Southwest logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/169:43 am
ORF
- SFB
1 stop27h 08m
Multiple Airlines
Sat 8/228:30 am
SFB
- ORF
2 stops27h 55m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/169:43 am
ORF
- SFB
1 stop27h 08m
Multiple Airlines
Mon 8/2410:09 am
SFB
- ORF
2 stops26h 16m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$471
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 10/157:30 am
ORF
- SFB
2 stops24h 29m
Multiple Airlines
Sun 10/186:09 pm
SFB
- ORF
1 stop16h 33m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$528
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 10/19:50 pm
ORF
- SFB
2 stops14h 32m
Multiple Airlines
Sun 10/47:31 pm
SFB
- ORF
1 stop15h 11m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$529
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/169:43 am
ORF
- SFB
1 stop27h 08m
Multiple Airlines
Thu 8/2010:00 am
SFB
- ORF
1 stop24h 40m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$536
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 7/28![Multiple Airlines logo]()
$767
Last-minute flights from Chesapeake to OrlandoDiscover last-minute flight deals from Chesapeake to Orlando. Data last updated July 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Orlando. Data last updated July 30, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/28. 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 8/159:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Sun 8/232:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 7/28![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 8/1512:16 pm
ORF
- MCO
1 stop7h 41m
Frontier
Mon 8/176:48 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 7/25![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/179:53 pm
ORF
- MCO
Nonstop2h 13m
Multiple Airlines
Sun 8/239:52 am
MCO
- ORF
Nonstop2h 18m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$166
This Priceline deal was found by Cheapflights users on 7/26. 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 8/179:53 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Sun 8/232:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 7/26![Frontier logo]()
$168
This Super.com deal was found by Cheapflights users on 7/26. 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 8/185:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Sun 8/232:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 7/26![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/199:06 am
ORF
- MCO
Nonstop2h 16m
Multiple Airlines
Sat 8/225:23 pm
MCO
- ORF
1 stop19h 02m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/207:00 am
ORF
- MCO
Nonstop2h 12m
Multiple Airlines
Fri 8/215:23 pm
MCO
- ORF
1 stop19h 02m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 8/205:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Sun 8/3010:03 am
MCO
- ORF
1 stop26h 22m
Frontier
Deal found 7/25![Frontier logo]()
$160
This Flightnetwork deal was found by Cheapflights users on 7/26. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:00 am
ORF
- MCO
Nonstop2h 12m
Multiple Airlines
Mon 8/242:03 pm
MCO
- ORF
Nonstop2h 08m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/231:20 pm
ORF
- MCO
1 stop6h 40m
Frontier
Wed 8/265:24 am
MCO
- ORF
1 stop7h 01m
Frontier
Deal found 7/27![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/251:20 pm
ORF
- MCO
1 stop5h 13m
Frontier
Tue 9/15:24 am
MCO
- ORF
1 stop7h 01m
Frontier
Deal found 7/28![Frontier logo]()
$162
This Frontier deal was found by Cheapflights users on 7/28. 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 8/285:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Sun 8/302:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 7/28![Frontier logo]()
$163
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 30, 2026.
Search for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated July 30, 2026.
This Frontier deal was found by Cheapflights users on 7/29. 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 7/29![Frontier logo]()
$84
This Frontier deal was found by Cheapflights users on 7/26. 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 8/285:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Deal found 7/26![Frontier logo]()
$85
This Frontier deal was found by Cheapflights users on 7/26. 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 9/267:43 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Deal found 7/26![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 10/116:00 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Deal found 7/27![Breeze Airways logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 8/1412:10 pm
ORF
- MCO
1 stop26h 13m
Frontier
Deal found 7/25![Frontier logo]()
$92
This Frontier deal was found by Cheapflights users on 7/26. 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.
Sun 8/169:34 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Deal found 7/26![Frontier logo]()
$94
This CheapOair deal was found by Cheapflights users on 7/25. 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 8/167:00 am
ORF
- MCO
Nonstop2h 12m
Breeze Airways
Deal found 7/25![Breeze Airways logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 8/299:06 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Deal found 7/29![Breeze Airways logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 8/231:20 pm
ORF
- MCO
1 stop8h 54m
Frontier
Deal found 7/25![Frontier logo]()
$100
This Southwest deal was found by Cheapflights users on 7/28. 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 8/1810:05 am
ORF
- MCO
Nonstop2h 10m
Southwest
Deal found 7/28![Southwest logo]()
$104
This Super.com deal was found by Cheapflights users on 7/27. 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.
Fri 9/257:43 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Deal found 7/27![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/301:20 pm
ORF
- SFB
2 stops26h 30m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$116
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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $158 (Frontier) |
One-way from | $84 (Frontier) |
Popular in | April |
Cheapest in | February |
Average price | $228 |
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 30, 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 9/2
10:05 am-12:15 pm
Nonstop2h 10m
Orlando
Wed 9/9
9:00 am-5:20 pm
2 stops8h 20m
$222
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Tue 8/25
1:51 pm-7:48 pm
1 stop5h 57m
Orlando
Tue 9/1
10:05 am-5:08 pm
1 stop7h 03m
$227
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 8/19
12:15 pm-7:00 pm
1 stop6h 45m
Orlando
Sat 8/29
6:25 am-3:00 pm
2 stops8h 35m
$232
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 8/22
9:55 am-4:55 pm
2 stops7h 00m
Orlando
Sat 8/29
7:10 am-11:45 am
1 stop4h 35m
$232
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 10/24
7:55 am-4:05 pm
2 stops8h 10m
Orlando
Sat 10/31
7:40 am-11:55 am
1 stop4h 15m
$232
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Fri 9/11
3:45 pm-10:55 pm
2 stops7h 10m
Orlando
Tue 9/15
9:00 am-5:20 pm
2 stops8h 20m
$258
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Fri 10/2
6:25 am-11:35 am
1 stop5h 10m
Orlando
Mon 10/5
3:40 pm-11:35 pm
2 stops7h 55m
$258
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Mon 9/7
6:00 am-12:20 pm
1 stop6h 20m
Orlando
Fri 9/11
9:30 am-5:55 pm
2 stops8h 25m
$288
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 12/2
3:05 pm-11:20 pm
2 stops8h 15m
Orlando
Fri 12/11
9:05 am-5:15 pm
2 stops8h 10m
$290
Quickest round-trip
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Mon 12/7
6:00 am-8:16 am
Nonstop2h 16m
Orlando
Fri 12/11
12:57 pm-3:04 pm
Nonstop2h 07m
$298
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
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 30, 2026.
It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 40% 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?
Airfare is typical for this route at the moment.
Chesapeake to Orlando flights typically cost between $140 and $250 in August.The cheapest round-trip price found within the last 5 days was $158 on Frontier (Aug 15-Aug 23).
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 25, 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 30, 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.
Crew
8.7
Boarding
8.3
Entertainment
6.7
Overall
8.2
Food
6.7
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.7
Boarding
8.3
Entertainment
6.7
Overall
8.2
Food
6.7
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.7
Boarding
8.3
Entertainment
6.7
Overall
8.2
Food
6.7
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.7
Boarding
8.3
Entertainment
6.7
Overall
8.2
Food
6.7
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.7
Boarding
8.3
Entertainment
6.7
Overall
8.2
Food
6.7
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.7
Boarding
8.3
Entertainment
6.7
Overall
8.2
Food
6.7
Comfort
8.2
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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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 30, 2026.
Chesapeake and Orlando flights
Browse other Chesapeake and Orlando flight options. Last updated on July 30, 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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$154 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$288 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$98 | Average$210 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$100 | Average$315 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$250 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$109 | Average$248 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$362 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$530 | FlexibilityNo cancel fee | On-time69% |