$43+ Cheap flights from Chesapeake, VA to Orlando (ORL)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
May 4 — May 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 Saturday
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 April 4, 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 April 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:15 pm
ORF
- MCO
Nonstop2h 07m
Spirit Airlines
Sun 5/104:50 pm
MCO
- ORF
Nonstop1h 59m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$97
This Priceline deal was found by Cheapflights users on 4/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:49 pm
ORF
- MCO
Nonstop2h 15m
Frontier
Thu 5/286:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 4/2![Frontier logo]()
$98
This Frontier deal was found by Cheapflights users on 4/2. 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.
Sun 4/1912:32 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Sat 4/254:16 pm
MCO
- ORF
Nonstop2h 05m
Frontier
Deal found 4/2![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/133:54 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Thu 4/165:40 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 3/31![Frontier logo]()
$100
This CheapOair deal was found by Cheapflights users on 4/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:45 am
ORF
- MCO
Nonstop2h 06m
Multiple Airlines
Mon 4/203:02 pm
MCO
- ORF
Nonstop2h 05m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$101
This Frontier deal was found by Cheapflights users on 4/4. 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 5/412:31 pm
ORF
- MCO
1 stop8h 21m
Frontier
Thu 5/76:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 4/4![Frontier logo]()
$102
This Frontier deal was found by Cheapflights users on 4/2. 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.
Sun 4/1912:32 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Fri 4/2411:10 am
MCO
- ORF
Nonstop2h 04m
Frontier
Deal found 4/2![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 4/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:16 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Mon 4/276:02 pm
MCO
- ORF
Nonstop2h 04m
Frontier
Deal found 4/4![Frontier logo]()
$104
This Expedia deal was found by Cheapflights users on 4/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:45 am
ORF
- MCO
Nonstop2h 06m
Multiple Airlines
Thu 4/165:40 pm
MCO
- ORF
Nonstop2h 06m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/1811:27 am
ORF
- MCO
1 stop20h 12m
Frontier
Sat 4/254:16 pm
MCO
- ORF
Nonstop2h 05m
Frontier
Deal found 4/3![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:41 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Sun 4/267:00 am
MCO
- ORF
Nonstop2h 05m
Frontier
Deal found 3/31![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:24 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Thu 4/165:40 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 3/31![Frontier logo]()
$109
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 April 4, 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 April 4, 2026.
This Southwest deal was found by Cheapflights users on 4/3. 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.
Sat 6/63:10 pm
ORF
- MCO
1 stop5h 00m
Southwest
Tue 6/93:10 pm
MCO
- ORF
2 stops7h 25m
Southwest
Deal found 4/3![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 4/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/62:30 pm
ORF
- MCO
1 stop7h 22m
Delta
Mon 6/85:45 pm
MCO
- ORF
1 stop6h 57m
Delta
Deal found 4/4![Delta logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 5/210:31 pm
ORF
- SFB
1 stop22h 16m
Multiple Airlines
Thu 5/76:46 pm
SFB
- ORF
1 stop15h 54m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/36:50 am
ORF
- MCO
2 stops8h 10m
Southwest
Sat 6/66:30 am
MCO
- ORF
2 stops8h 45m
Southwest
Deal found 3/31![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 4/1. 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 5/138:40 am
ORF
- MCO
2 stops6h 20m
Southwest
Sun 5/1710:55 pm
MCO
- ORF
1 stop10h 30m
Southwest
Deal found 4/1![Southwest logo]()
$238
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/157:59 pm
ORF
- MCO
1 stop4h 56m
Delta
Sat 5/2312:00 pm
MCO
- ORF
1 stop6h 55m
Delta
Deal found 3/31![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 4/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:35 pm
ORF
- MCO
1 stop4h 25m
Southwest
Thu 5/282:00 pm
MCO
- ORF
2 stops8h 55m
Southwest
Deal found 4/2![Southwest logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/610:31 pm
ORF
- SFB
1 stop19h 34m
Multiple Airlines
Sun 5/106:46 pm
SFB
- ORF
1 stop15h 54m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 4/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/134:54 pm
ORF
- MCO
1 stop5h 57m
Delta
Sat 6/206:45 pm
MCO
- ORF
1 stop5h 53m
Delta
Deal found 4/3![Delta logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Sat 5/210:31 pm
ORF
- SFB
1 stop22h 16m
Multiple Airlines
Sun 5/106:46 pm
SFB
- ORF
1 stop15h 54m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 4/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/124:43 pm
ORF
- MCO
1 stop7h 09m
Delta
Sat 6/206:45 pm
MCO
- ORF
1 stop5h 53m
Delta
Deal found 4/3![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:15 am
ORF
- MCO
2 stops9h 20m
Southwest
Thu 5/146:05 pm
MCO
- ORF
1 stop4h 50m
Southwest
Deal found 3/31![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 4/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:10 am
ORF
- MCO
2 stops6h 45m
Southwest
Sat 4/253:05 pm
MCO
- ORF
2 stops8h 00m
Southwest
Deal found 4/2![Southwest logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
Fri 5/2911:25 am
ORF
- SFB
1 stop12h 13m
Multiple Airlines
Sun 5/319:28 pm
SFB
- ORF
2 stops19h 11m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/38:40 am
ORF
- MCO
2 stops6h 20m
Southwest
Fri 6/53:30 pm
MCO
- ORF
2 stops8h 05m
Southwest
Deal found 3/31![Southwest logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
Sun 5/107:05 am
ORF
- SFB
2 stops10h 51m
Multiple Airlines
Thu 5/146:46 pm
SFB
- ORF
1 stop15h 54m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 7/3111:25 am
ORF
- SFB
1 stop12h 02m
Multiple Airlines
Mon 8/31:57 pm
SFB
- ORF
2 stops8h 51m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Thu 4/3010:04 pm
ORF
- SFB
2 stops24h 22m
Multiple Airlines
Thu 5/76:46 pm
SFB
- ORF
1 stop15h 54m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1510:31 pm
ORF
- SFB
1 stop22h 16m
Multiple Airlines
Sun 4/191:41 pm
SFB
- ORF
2 stops8h 45m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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
Sun 6/288:58 pm
SFB
- ORF
2 stops19h 55m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$623
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/2712:17 pm
SFB
- ORF
1 stop25h 12m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$632
Last-minute flights from Chesapeake to OrlandoDiscover last-minute flight deals from Chesapeake to Orlando. Data last updated April 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Orlando. Data last updated April 4, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:24 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Thu 4/165:40 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 3/31![Frontier logo]()
$109
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/133:54 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Thu 4/165:40 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 3/31![Frontier logo]()
$100
This Frontier deal was found by Cheapflights users on 4/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/133:54 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Mon 4/203:02 pm
MCO
- ORF
Nonstop2h 05m
Frontier
Deal found 4/3![Frontier logo]()
$101
This Expedia deal was found by Cheapflights users on 4/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:45 am
ORF
- MCO
Nonstop2h 06m
Multiple Airlines
Thu 4/165:40 pm
MCO
- ORF
Nonstop2h 06m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/1811:27 am
ORF
- MCO
1 stop20h 12m
Frontier
Sat 4/254:16 pm
MCO
- ORF
Nonstop2h 05m
Frontier
Deal found 4/3![Frontier logo]()
$106
This Frontier deal was found by Cheapflights users on 4/2. 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.
Sun 4/1912:32 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Sat 4/254:16 pm
MCO
- ORF
Nonstop2h 05m
Frontier
Deal found 4/2![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 4/2. 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.
Sun 4/1912:32 pm
ORF
- MCO
Nonstop2h 10m
Frontier
Fri 4/2411:10 am
MCO
- ORF
Nonstop2h 04m
Frontier
Deal found 4/2![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:41 pm
ORF
- MCO
Nonstop2h 12m
Frontier
Sun 4/267:00 am
MCO
- ORF
Nonstop2h 05m
Frontier
Deal found 3/31![Frontier logo]()
$107
This Super.com deal was found by Cheapflights users on 4/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:16 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Mon 4/276:02 pm
MCO
- ORF
Nonstop2h 04m
Frontier
Deal found 4/4![Frontier logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:15 pm
ORF
- MCO
Nonstop2h 07m
Spirit Airlines
Sun 5/104:50 pm
MCO
- ORF
Nonstop1h 59m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$97
This Frontier deal was found by Cheapflights users on 4/4. 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 5/412:31 pm
ORF
- MCO
1 stop8h 21m
Frontier
Thu 5/76:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 4/4![Frontier logo]()
$102
This Priceline deal was found by Cheapflights users on 4/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:49 pm
ORF
- MCO
Nonstop2h 15m
Frontier
Thu 5/286:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 4/2![Frontier logo]()
$98
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 April 4, 2026.
Search for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated April 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:45 am
ORF
- MCO
Nonstop2h 06m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$43
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/19:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 3/31![Frontier logo]()
$44
This Super.com deal was found by Cheapflights users on 3/30. 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 Super.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
Deal found 3/30![Frontier logo]()
$49
This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
Sat 5/167:44 pm
ORF
- MCO
Nonstop2h 05m
Spirit Airlines
Deal found 4/2![Spirit Airlines logo]()
$50
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:59 pm
ORF
- MCO
Nonstop2h 04m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$51
This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
Sun 5/310:13 am
ORF
- MCO
Nonstop2h 09m
Frontier
Deal found 4/2![Frontier logo]()
$52
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 5/289:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 4/1![Frontier logo]()
$53
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 3/31![Frontier logo]()
$54
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:45 am
ORF
- MCO
Nonstop2h 06m
Spirit Airlines
Deal found 4/2![Spirit Airlines logo]()
$55
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 6/239:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 4/1![Frontier logo]()
$58
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/299:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 3/31![Frontier logo]()
$59
This Trip.com deal was found by Cheapflights users on 4/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:06 pm
ORF
- MCO
1 stop9h 41m
Frontier
Deal found 4/3![Frontier logo]()
$60
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 April 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $97 (Cheapflightsfares) |
One-way from | $43 (Cheapflightsfares) |
Popular in | April |
Cheapest in | May |
Average price | $252 |
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 April 4, 2026.
Use the filters below to find and compare flights from Chesapeake to Orlando that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 6/6
3:10 pm-8:10 pm
1 stop5h 00m
Orlando
Tue 6/9
3:10 pm-10:35 pm
2 stops7h 25m
$232
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 6/6
2:30 pm-9:52 pm
1 stop7h 22m
Orlando
Mon 6/8
5:45 pm-12:42 am
1 stop6h 57m
$237
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 6/3
6:50 am-3:00 pm
2 stops8h 10m
Orlando
Sat 6/6
6:30 am-3:15 pm
2 stops8h 45m
$237
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 5/13
8:40 am-3:00 pm
2 stops6h 20m
Orlando
Sun 5/17
10:55 pm-9:25 am
1 stop10h 30m
$238
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sun 5/17
8:35 pm-1:00 am
1 stop4h 25m
Orlando
Thu 5/28
2:00 pm-10:55 pm
2 stops8h 55m
$263
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Fri 5/15
7:59 pm-12:55 am
1 stop4h 56m
Orlando
Sat 5/23
12:00 pm-6:55 pm
1 stop6h 55m
$276
NorfolkOrlando
ORF - SFB
ORFSFB
Norfolk
Sat 5/2
10:31 pm-8:47 pm
1 stop22h 16m
Orlando Sanford Intl
Thu 5/7
6:46 pm-10:40 am
1 stop15h 54m
$293
Quickest round-trip
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 6/13
4:54 pm-10:51 pm
1 stop5h 57m
Orlando
Sat 6/20
6:45 pm-12:38 am
1 stop5h 53m
$294
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Fri 6/12
4:43 pm-11:52 pm
1 stop7h 09m
Orlando
Sat 6/20
6:45 pm-12:38 am
1 stop5h 53m
$294
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sun 5/10
6:15 am-3:35 pm
2 stops9h 20m
Orlando
Thu 5/14
6:05 pm-10:55 pm
1 stop4h 50m
$294
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
How far ahead should I book a flight from Chesapeake to Orlando?
Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Orlando. Price data was last updated on April 3, 2026.
To ensure you get the cheapest price possible for a flight from Chesapeake to Orlando, you should look to book at least 90 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chesapeake to Orlando?
Currently, September is the cheapest month in which you can book a flight from Chesapeake to Orlando (average of $42). Flying from Chesapeake to Orlando in December is currently the most expensive (average of $84). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from C6E to ORL?
Find hourly flight availability from Chesapeake to Orlando. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 4, 2026.
It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 36% 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 April 4, 2026.
Travelers seeking maximum savings on their Chesapeake to Orlando flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chesapeake to Orlando
Explore weekly flight availability from Chesapeake to Orlando. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 4, 2026.
The most flights from C6E to ORL are scheduled on a Friday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Chesapeake to Orlando?
Reviews of airlines servicing Orlando
Get insights into the airlines that provide service to Orlando. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Orlando. Reviews last updated April 4, 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.
Overall
8.1
Food
6.6
Boarding
8.3
Entertainment
6.6
Crew
8.7
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.1
Food
6.6
Boarding
8.3
Entertainment
6.6
Crew
8.7
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.1
Food
6.6
Boarding
8.3
Entertainment
6.6
Crew
8.7
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.1
Food
6.6
Boarding
8.3
Entertainment
6.6
Crew
8.7
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.1
Food
6.6
Boarding
8.3
Entertainment
6.6
Crew
8.7
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.1
Food
6.6
Boarding
8.3
Entertainment
6.6
Crew
8.7
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.
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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Orlando by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chesapeake to Orlando by cabin class
Find flights from Chesapeake to Orlando, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Orlando
Explore flights to Orlando departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 4, 2026.
Chesapeake and Orlando flights
Browse other Chesapeake and Orlando flight options. Last updated on April 4, 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 April 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$42 | Average$130 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$58 | Average$144 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$78 | Average$162 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$88 | Average$294 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$91 | Average$248 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$97 | Average$226 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$294 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$138 | Average$437 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$159 | Average$330 | FlexibilityNo cancel fee | On-time71% |