$64+ Cheap flights from Chesapeake, VA to Orlando (ORL)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Jul 29 — Aug 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 August, booked 90 days in advance, depart on a Sunday or Monday and return on a Thursday
Cheap flight deals from Chesapeake to Orlando
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Best
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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 29, 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 29, 2026.
This Frontier deal was found by Cheapflights users on 6/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Wed 9/22:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 6/24![Frontier logo]()
$133
This Frontier deal was found by Cheapflights users on 6/28. 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.
Tue 9/15:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Wed 9/22:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 6/28![Frontier logo]()
$136
This Frontier deal was found by Cheapflights users on 6/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Sat 9/123:12 pm
MCO
- ORF
Nonstop2h 03m
Frontier
Deal found 6/27![Frontier logo]()
$143
This Super.com deal was found by Cheapflights users on 6/28. 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 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
Sat 9/123:12 pm
MCO
- ORF
Nonstop2h 03m
Frontier
Deal found 6/28![Frontier logo]()
$144
This Frontier deal was found by Cheapflights users on 6/25. 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 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 6/25![Frontier logo]()
$145
This Expedia deal was found by Cheapflights users on 6/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Wed 9/163:12 pm
MCO
- ORF
Nonstop2h 03m
Frontier
Deal found 6/29![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 9/55:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Sat 9/123:12 pm
MCO
- ORF
Nonstop2h 03m
Frontier
Deal found 6/27![Frontier logo]()
$147
This Frontier deal was found by Cheapflights users on 6/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Tue 8/252:03 pm
MCO
- ORF
Nonstop2h 08m
Frontier
Deal found 6/24![Frontier logo]()
$148
This Frontier deal was found by Cheapflights users on 6/24. 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 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 6/24![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 6/26. 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.
Sat 8/110:31 pm
ORF
- SFB
1 stop12h 50m
Multiple Airlines
Thu 8/612:14 pm
SFB
- ORF
2 stops11h 39m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 8/66:00 am
ORF
- SFB
2 stops34h 41m
Multiple Airlines
Thu 8/139:02 am
SFB
- ORF
1 stop25h 38m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Fri 8/1412:10 pm
ORF
- SFB
2 stops44h 22m
Multiple Airlines
Thu 8/2010:00 am
SFB
- ORF
1 stop24h 40m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$348
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 29, 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 29, 2026.
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:30 pm
ORF
- MCO
1 stop4h 56m
Delta
Tue 11/176:30 pm
MCO
- ORF
1 stop5h 44m
Delta
Deal found 6/28![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 6/27. 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.
Sat 8/2211:35 am
ORF
- MCO
2 stops6h 30m
Southwest
Tue 8/259:00 am
MCO
- ORF
2 stops8h 20m
Southwest
Deal found 6/27![Southwest logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 6/26. 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.
Sat 8/110:31 pm
ORF
- SFB
1 stop12h 50m
Multiple Airlines
Thu 8/612:14 pm
SFB
- ORF
2 stops11h 39m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:15 pm
ORF
- MCO
1 stop6h 03m
Delta
Mon 10/56:40 pm
MCO
- ORF
1 stop5h 53m
Delta
Deal found 6/28![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 6/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:55 am
ORF
- MCO
2 stops7h 00m
Southwest
Sat 9/126:15 am
MCO
- ORF
1 stop5h 30m
Southwest
Deal found 6/26![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 6/28. 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.
Mon 11/166:10 pm
ORF
- MCO
1 stop4h 20m
Southwest
Fri 11/206:55 pm
MCO
- ORF
1 stop4h 35m
Southwest
Deal found 6/28![Southwest logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 8/66:00 am
ORF
- SFB
2 stops34h 41m
Multiple Airlines
Thu 8/139:02 am
SFB
- ORF
1 stop25h 38m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 6/28. 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.
Sat 11/149:00 am
ORF
- MCO
2 stops9h 55m
Southwest
Sat 11/213:15 pm
MCO
- ORF
2 stops8h 10m
Southwest
Deal found 6/28![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Fri 8/1412:10 pm
ORF
- SFB
2 stops44h 22m
Multiple Airlines
Thu 8/2010:00 am
SFB
- ORF
1 stop24h 40m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 6/24. 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.
Sat 7/256:00 am
ORF
- MCO
2 stops8h 30m
Southwest
Wed 7/291:30 pm
MCO
- ORF
1 stop8h 25m
Southwest
Deal found 6/24![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1810:31 pm
ORF
- SFB
1 stop13h 05m
Multiple Airlines
Thu 7/239:23 pm
SFB
- ORF
2 stops37h 58m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 6/24. 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 7/2912:25 pm
ORF
- MCO
2 stops7h 05m
Southwest
Sun 8/22:25 pm
MCO
- ORF
2 stops7h 40m
Southwest
Deal found 6/24![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 6/25. 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 8/19:55 am
ORF
- MCO
2 stops5h 50m
Southwest
Sun 8/910:30 am
MCO
- ORF
1 stop5h 30m
Southwest
Deal found 6/25![Southwest logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 7/1311:25 am
ORF
- SFB
1 stop12h 02m
Multiple Airlines
Sat 7/189:19 pm
SFB
- ORF
2 stops37h 56m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$405
This Southwest deal was found by Cheapflights users on 6/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:25 pm
ORF
- MCO
2 stops6h 15m
Southwest
Sat 10/103:35 pm
MCO
- ORF
2 stops5h 50m
Southwest
Deal found 6/26![Southwest logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2910:31 pm
ORF
- SFB
1 stop12h 45m
Multiple Airlines
Sun 8/29:19 pm
SFB
- ORF
2 stops25h 49m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Sat 7/1810:31 pm
ORF
- SFB
1 stop13h 05m
Multiple Airlines
Tue 7/2112:47 pm
SFB
- ORF
2 stops20h 19m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 6/24. 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.
Fri 11/205:55 pm
ORF
- MCO
1 stop6h 25m
Southwest
Wed 11/257:35 am
MCO
- ORF
1 stop5h 15m
Southwest
Deal found 6/24![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 6/28. 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 7/246:30 am
ORF
- MCO
Nonstop2h 00m
Southwest
Wed 7/299:45 am
MCO
- ORF
Nonstop2h 00m
Southwest
Deal found 6/28![Southwest logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 10/159:50 pm
ORF
- SFB
2 stops14h 32m
Multiple Airlines
Sun 10/186:09 pm
SFB
- ORF
1 stop16h 33m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$526
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 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
Wed 11/251:14 pm
SFB
- ORF
2 stops23h 54m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$558
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/223:49 pm
ORF
- SFB
2 stops7h 35m
Multiple Airlines
Sun 11/296:11 pm
SFB
- ORF
1 stop16h 31m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$740
Last-minute flights from Chesapeake to OrlandoDiscover last-minute flight deals from Chesapeake to Orlando. Data last updated June 29, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Orlando. Data last updated June 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 7/1311:25 am
ORF
- SFB
1 stop12h 02m
Multiple Airlines
Sat 7/189:19 pm
SFB
- ORF
2 stops37h 56m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$405
This Frontier deal was found by Cheapflights users on 6/25. 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 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 6/25![Frontier logo]()
$145
This Frontier deal was found by Cheapflights users on 6/24. 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 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 6/24![Frontier logo]()
$150
This Frontier deal was found by Cheapflights users on 6/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Wed 7/226:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/24![Frontier logo]()
$153
This Super.com deal was found by Cheapflights users on 6/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Tue 7/216:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/25![Frontier logo]()
$156
This Frontier deal was found by Cheapflights users on 6/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Sat 7/256:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/24![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1810:31 pm
ORF
- SFB
1 stop13h 05m
Multiple Airlines
Thu 7/239:23 pm
SFB
- ORF
2 stops37h 58m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Sat 7/1810:31 pm
ORF
- SFB
1 stop13h 05m
Multiple Airlines
Tue 7/2112:47 pm
SFB
- ORF
2 stops20h 19m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$413
This Super.com deal was found by Cheapflights users on 6/28. 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 Super.com 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
Tue 7/286:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/28![Frontier logo]()
$146
This Frontier deal was found by Cheapflights users on 6/25. 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 Frontier 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
Wed 7/296:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/25![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Wed 7/296:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/24![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2910:31 pm
ORF
- SFB
1 stop12h 45m
Multiple Airlines
Sun 8/29:19 pm
SFB
- ORF
2 stops25h 49m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$409
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 29, 2026.
Search for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated June 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:10 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/24![Frontier logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 8/315:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Deal found 6/26![Frontier logo]()
$68
This Frontier deal was found by Cheapflights users on 6/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Deal found 6/24![Frontier logo]()
$69
This Super.com deal was found by Cheapflights users on 6/27. 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.
Tue 8/255:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Deal found 6/27![Frontier logo]()
$71
This Frontier deal was found by Cheapflights users on 6/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:06 pm
ORF
- MCO
Nonstop2h 11m
Frontier
Deal found 6/27![Frontier logo]()
$72
This Super.com deal was found by Cheapflights users on 6/24. 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 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
Deal found 6/24![Frontier logo]()
$73
This Frontier deal was found by Cheapflights users on 6/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:10 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/24![Frontier logo]()
$74
This Frontier deal was found by Cheapflights users on 6/25. 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 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 6/25![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:57 pm
ORF
- MCO
1 stop9h 13m
Frontier
Deal found 6/24![Frontier logo]()
$79
This eDestinos deal was found by Cheapflights users on 6/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/28![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:31 pm
ORF
- SFB
1 stop20h 16m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 8/212:10 pm
ORF
- SFB
2 stops29h 02m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$140
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 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $133 (Frontier) |
One-way from | $64 (Kiwi.com) |
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 29, 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
Mon 11/16
12:30 pm-5:26 pm
1 stop4h 56m
Orlando
Tue 11/17
6:30 pm-12:14 am
1 stop5h 44m
$233
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Thu 10/1
7:15 pm-1:18 am
1 stop6h 03m
Orlando
Mon 10/5
6:40 pm-12:33 am
1 stop5h 53m
$233
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 8/22
11:35 am-6:05 pm
2 stops6h 30m
Orlando
Tue 8/25
9:00 am-5:20 pm
2 stops8h 20m
$265
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 9/5
9:55 am-4:55 pm
2 stops7h 00m
Orlando
Sat 9/12
6:15 am-11:45 am
1 stop5h 30m
$266
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Mon 11/16
6:10 pm-10:30 pm
1 stop4h 20m
Orlando
Fri 11/20
6:55 pm-11:30 pm
1 stop4h 35m
$303
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 11/14
9:00 am-6:55 pm
2 stops9h 55m
Orlando
Sat 11/21
3:15 pm-11:25 pm
2 stops8h 10m
$307
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 7/25
6:00 am-2:30 pm
2 stops8h 30m
Orlando
Wed 7/29
1:30 pm-9:55 pm
1 stop8h 25m
$307
NorfolkOrlando
ORF - SFB
ORFSFB
Norfolk
Sat 8/1
10:31 pm-11:21 am
1 stop12h 50m
Orlando Sanford Intl
Thu 8/6
12:14 pm-11:53 pm
2 stops11h 39m
$313
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 7/29
12:25 pm-7:30 pm
2 stops7h 05m
Orlando
Sun 8/2
2:25 pm-10:05 pm
2 stops7h 40m
$327
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 8/1
9:55 am-3:45 pm
2 stops5h 50m
Orlando
Sun 8/9
10:30 am-4:00 pm
1 stop5h 30m
$332
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 29, 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 29, 2026.
The most flights from C6E to ORL are scheduled on a Monday (5 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 27, 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 29, 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
8.8
Overall
8.2
Boarding
8.4
Comfort
8.2
Entertainment
6.7
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Overall
8.2
Boarding
8.4
Comfort
8.2
Entertainment
6.7
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Overall
8.2
Boarding
8.4
Comfort
8.2
Entertainment
6.7
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Overall
8.2
Boarding
8.4
Comfort
8.2
Entertainment
6.7
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Overall
8.2
Boarding
8.4
Comfort
8.2
Entertainment
6.7
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Overall
8.2
Boarding
8.4
Comfort
8.2
Entertainment
6.7
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
Find useful and relevant information for your journey from Chesapeake to Orlando. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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 29, 2026.
Chesapeake and Orlando flights
Browse other Chesapeake and Orlando flight options. Last updated on June 29, 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 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$57 | Average$150 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$297 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$98 | Average$210 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$99 | Average$304 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$105 | Average$244 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$109 | Average$247 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$446 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$158 | Average$345 | FlexibilityNo cancel fee | On-time71% |