$41+ 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 6/14. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Jun 4 — Jun 111
Round-trip
1 adult, Economy
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Find cheap flights from Chesapeake to Orlando with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in May or February, booked 90 days in advance, depart on a Sunday or Thursday and return on a Thursday
Cheap flight deals from Chesapeake to Orlando
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Best
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Cheapest flights from Chesapeake to OrlandoExplore the most affordable flight options available from Chesapeake to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 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 May 5, 2026.
This deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:10 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Mon 9/213:12 pm
MCO
- ORF
Nonstop2h 03m
Frontier
Deal found 4/30![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/47:43 pm
ORF
- MCO
Nonstop2h 01m
Multiple Airlines
Mon 6/86:11 pm
MCO
- ORF
Nonstop2h 06m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/16:00 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Fri 5/86:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 4/30![Frontier logo]()
$93
This eDestinos deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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.
Wed 6/247:35 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Fri 7/36:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/2![Frontier logo]()
$94
This eDestinos deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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.
Thu 6/49:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Mon 6/86:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 5/1![Frontier logo]()
$96
This Frontier deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/2![Frontier logo]()
$98
This Priceline deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/119:12 pm
ORF
- MCO
Nonstop2h 16m
Multiple Airlines
Fri 5/228:20 pm
MCO
- ORF
Nonstop2h 18m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 6/89:12 pm
ORF
- MCO
Nonstop2h 16m
Multiple Airlines
Fri 6/124:51 pm
MCO
- ORF
Nonstop1h 57m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$103
This Mytrip deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:24 pm
ORF
- MCO
Nonstop2h 16m
Multiple Airlines
Sat 5/234:50 pm
MCO
- ORF
Nonstop1h 59m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/2612:06 pm
ORF
- MCO
1 stop9h 41m
Frontier
Thu 5/286:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 4/30![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/299:12 pm
ORF
- MCO
Nonstop2h 16m
Multiple Airlines
Sun 5/314:50 pm
MCO
- ORF
Nonstop1h 59m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/811:25 am
ORF
- SFB
1 stop12h 10m
Multiple Airlines
Fri 6/121:16 pm
SFB
- ORF
2 stops9h 32m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$303
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 May 5, 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 May 5, 2026.
This Breeze Airways deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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.
Wed 6/39:06 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Mon 6/88:20 pm
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 5/4![Breeze Airways logo]()
$203
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/266:25 am
ORF
- MCO
Nonstop2h 05m
Southwest
Wed 5/276:50 pm
MCO
- ORF
Nonstop2h 00m
Southwest
Deal found 4/30![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/34:39 pm
ORF
- MCO
1 stop6h 05m
Delta
Sat 6/610:59 am
MCO
- ORF
1 stop7h 18m
Delta
Deal found 4/30![Delta logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/811:25 am
ORF
- SFB
1 stop12h 10m
Multiple Airlines
Fri 6/121:16 pm
SFB
- ORF
2 stops9h 32m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$303
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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.
Wed 6/36:05 am
ORF
- MCO
2 stops7h 58m
United Airlines
Mon 6/87:05 pm
MCO
- ORF
1 stop4h 39m
United Airlines
Deal found 5/4![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/15:25 pm
ORF
- MCO
1 stop5h 45m
Southwest
Sat 6/66:30 am
MCO
- ORF
2 stops8h 45m
Southwest
Deal found 5/4![Southwest logo]()
$258
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 6/24:25 pm
ORF
- MCO
1 stop4h 30m
Southwest
Fri 6/53:30 pm
MCO
- ORF
2 stops8h 05m
Southwest
Deal found 4/30![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2010:31 pm
ORF
- SFB
1 stop13h 20m
Multiple Airlines
Sun 5/249:18 pm
SFB
- ORF
2 stops37h 53m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 7/26:10 pm
ORF
- MCO
1 stop6h 35m
Southwest
Tue 7/78:00 am
MCO
- ORF
2 stops6h 25m
Southwest
Deal found 5/4![Southwest logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/310:31 pm
ORF
- SFB
1 stop12h 57m
Multiple Airlines
Sun 6/79:13 pm
SFB
- ORF
1 stop13h 27m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 7/14:30 pm
ORF
- MCO
1 stop7h 05m
Southwest
Thu 7/93:30 pm
MCO
- ORF
2 stops8h 05m
Southwest
Deal found 5/1![Southwest logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:31 pm
ORF
- SFB
1 stop19h 34m
Multiple Airlines
Thu 5/219:02 am
SFB
- ORF
1 stop25h 38m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/2011:55 am
ORF
- MCO
1 stop7h 45m
Southwest
Tue 6/238:00 am
MCO
- ORF
2 stops6h 25m
Southwest
Deal found 5/1![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/186:00 am
ORF
- MCO
2 stops7h 00m
Southwest
Tue 6/232:30 pm
MCO
- ORF
2 stops8h 05m
Southwest
Deal found 5/1![Southwest logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/319:52 pm
ORF
- SFB
2 stops15h 11m
Multiple Airlines
Sun 6/79:13 pm
SFB
- ORF
1 stop13h 27m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$424
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/133:10 pm
ORF
- MCO
2 stops7h 20m
Southwest
Fri 6/193:30 pm
MCO
- ORF
2 stops8h 05m
Southwest
Deal found 5/4![Southwest logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/76:00 am
ORF
- SFB
2 stops16h 29m
Multiple Airlines
Sun 6/148:58 am
SFB
- ORF
1 stop25h 42m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/266:00 am
ORF
- MCO
2 stops7h 00m
Southwest
Thu 7/23:30 pm
MCO
- ORF
2 stops8h 05m
Southwest
Deal found 5/3![Southwest logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/287:40 am
ORF
- SFB
2 stops15h 36m
Multiple Airlines
Sun 5/319:02 am
SFB
- ORF
1 stop25h 38m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2010:31 pm
ORF
- SFB
1 stop12h 52m
Multiple Airlines
Sat 6/279:07 pm
SFB
- ORF
2 stops38h 19m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/5![Multiple Airlines logo]()
$494
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/2211:25 am
ORF
- SFB
1 stop12h 13m
Multiple Airlines
Sun 5/249:06 am
SFB
- ORF
2 stops22h 25m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$536
Last-minute flights from Chesapeake to OrlandoDiscover last-minute flight deals from Chesapeake to Orlando. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Orlando. Data last updated May 5, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/119:12 pm
ORF
- MCO
Nonstop2h 16m
Multiple Airlines
Fri 5/228:20 pm
MCO
- ORF
Nonstop2h 18m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/119:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Fri 5/225:10 pm
MCO
- ORF
1 stop18h 05m
Frontier
Deal found 4/30![Frontier logo]()
$109
This Mytrip deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:24 pm
ORF
- MCO
Nonstop2h 16m
Multiple Airlines
Sat 5/234:50 pm
MCO
- ORF
Nonstop1h 59m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/2612:06 pm
ORF
- MCO
1 stop9h 41m
Frontier
Thu 5/286:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 4/30![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/2612:06 pm
ORF
- MCO
1 stop9h 41m
Multiple Airlines
Thu 5/284:50 pm
MCO
- ORF
Nonstop1h 59m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/299:12 pm
ORF
- MCO
Nonstop2h 16m
Multiple Airlines
Sun 5/314:50 pm
MCO
- ORF
Nonstop1h 59m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/299:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Sat 6/62:40 pm
MCO
- ORF
1 stop20h 31m
Frontier
Deal found 5/1![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/47:43 pm
ORF
- MCO
Nonstop2h 01m
Multiple Airlines
Mon 6/86:11 pm
MCO
- ORF
Nonstop2h 06m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$92
This eDestinos deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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.
Thu 6/49:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Mon 6/86:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 5/1![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 6/89:12 pm
ORF
- MCO
Nonstop2h 16m
Multiple Airlines
Fri 6/124:51 pm
MCO
- ORF
Nonstop1h 57m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/811:25 am
ORF
- SFB
1 stop12h 10m
Multiple Airlines
Fri 6/121:16 pm
SFB
- ORF
2 stops9h 32m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$303
This eDestinos deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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.
Wed 6/247:35 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Fri 7/36:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/2![Frontier logo]()
$94
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 May 5, 2026.
Search for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Booking.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/149:35 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 4/30![Frontier logo]()
$41
This Frontier deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/307:25 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 5/4![Frontier logo]()
$44
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:35 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 5/1![Frontier logo]()
$48
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:05 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Deal found 5/2![Breeze Airways logo]()
$53
This Frontier deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 10/276:10 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 5/4![Frontier logo]()
$54
This Frontier deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 5/1![Frontier logo]()
$57
This eDestinos deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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.
Mon 7/139:35 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 5/1![Frontier logo]()
$58
This Frontier deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 10/266:25 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 5/4![Frontier logo]()
$59
This Booking.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:06 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Deal found 5/1![Breeze Airways logo]()
$63
This Frontier deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 7/259:35 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 5/1![Frontier logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/112:06 pm
ORF
- MCO
1 stop26h 09m
Frontier
Deal found 5/5![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 10/266:00 am
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Deal found 5/2![Breeze Airways logo]()
$68
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 May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $90 |
One-way from | $41 (Booking.com) |
Popular in | April |
Cheapest in | May |
Average price | $131 |
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 May 5, 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 6/3
9:06 am-11:22 am
Nonstop2h 16m
Orlando
Mon 6/8
8:20 pm-10:38 pm
Nonstop2h 18m
$203
Quickest round-trip
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Tue 5/26
6:25 am-8:30 am
Nonstop2h 05m
Orlando
Wed 5/27
6:50 pm-8:50 pm
Nonstop2h 00m
$217
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 6/3
4:39 pm-10:44 pm
1 stop6h 05m
Orlando
Sat 6/6
10:59 am-6:17 pm
1 stop7h 18m
$240
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Mon 6/1
5:25 pm-11:10 pm
1 stop5h 45m
Orlando
Sat 6/6
6:30 am-3:15 pm
2 stops8h 45m
$258
NorfolkOrlando
ORF - SFB
ORFSFB
Norfolk
Mon 6/8
11:25 am-11:35 pm
1 stop12h 10m
Orlando Sanford Intl
Fri 6/12
1:16 pm-10:48 pm
2 stops9h 32m
$303
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Tue 6/2
4:25 pm-8:55 pm
1 stop4h 30m
Orlando
Fri 6/5
3:30 pm-11:35 pm
2 stops8h 05m
$307
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Thu 7/2
6:10 pm-12:45 am
1 stop6h 35m
Orlando
Tue 7/7
8:00 am-2:25 pm
2 stops6h 25m
$322
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 6/3
6:05 am-2:03 pm
2 stops7h 58m
Orlando
Mon 6/8
7:05 pm-11:44 pm
1 stop4h 39m
$325
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 7/1
4:30 pm-11:35 pm
1 stop7h 05m
Orlando
Thu 7/9
3:30 pm-11:35 pm
2 stops8h 05m
$332
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 6/20
11:55 am-7:40 pm
1 stop7h 45m
Orlando
Tue 6/23
8:00 am-2:25 pm
2 stops6h 25m
$337
Showing 1-10 of 44 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 May 5, 2026.
It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 37% on the flight price compared to flying at noon, which is usually more expensive.
What is the cheapest day to fly from Chesapeake to Orlando?
Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Orlando. Price data was last updated on May 2, 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.
How much does it cost to fly round-trip from Chesapeake to Orlando?
Reviews of airlines servicing Orlando
Get insights into the airlines that provide service to Orlando. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Orlando. Reviews last updated May 5, 2026.
Peruse reviews from past customers who have flown with Breeze Airways,Southwest, andAmerican Airlines from Chesapeake to Orlando to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.6
Entertainment
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Entertainment
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Entertainment
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Entertainment
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Entertainment
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Entertainment
6.6
Crew
8.7
Boarding
8.3
Comfort
8.2
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
Find useful and relevant information for your journey from Chesapeake to Orlando. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chesapeake to Orlando
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Complete your trip
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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 May 5, 2026.
Chesapeake and Orlando flights
Browse other Chesapeake and Orlando flight options. Last updated on May 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 9 airlines flying from Chesapeake to Orlando
Discover the top 9 airlines that operate flights from Chesapeake to Orlando. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$44 | Average$128 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$48 | Average$140 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$254 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$98 | Average$220 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$99 | Average$303 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$101 | Average$230 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$102 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$437 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$161 | Average$325 | FlexibilityNo cancel fee | On-time71% |