$68+ Cheap flights from Chesapeake, VA to Orlando (ORL)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Jun 29 — Jul 61
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 Friday and return on a Thursday
Cheap flight deals from Chesapeake to Orlando
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Cheapest flights from Chesapeake to OrlandoExplore the most affordable flight options available from Chesapeake to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 30, 2026.
Explore the most affordable flight options available from Chesapeake to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 30, 2026.
This Super.com deal was found by Cheapflights users on 5/25. 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.
Mon 8/319:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Wed 9/26:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/25![Frontier logo]()
$132
This Frontier deal was found by Cheapflights users on 5/25. 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.
Tue 9/19:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Wed 9/26:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/25![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 5/26. 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.
Tue 7/149:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Thu 7/166:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 5/26![Frontier logo]()
$152
This Priceline deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:34 pm
ORF
- MCO
Nonstop2h 13m
Multiple Airlines
Thu 7/169:52 am
MCO
- ORF
Nonstop2h 18m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:24 pm
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Mon 6/88:20 pm
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 5/25![Breeze Airways logo]()
$157
This Super.com deal was found by Cheapflights users on 5/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Fri 6/126:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/29![Frontier logo]()
$162
This Frontier deal was found by Cheapflights users on 5/27. 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.
Tue 6/307:25 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Sat 7/44:58 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/27![Frontier logo]()
$163
This Frontier deal was found by Cheapflights users on 5/25. 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 6/247:35 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Sat 7/44:58 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/25![Frontier logo]()
$165
This Super.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Mon 6/86:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 5/27![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 5/30. 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 7/3111:25 am
ORF
- SFB
1 stop12h 02m
Multiple Airlines
Sun 8/96:10 am
SFB
- ORF
2 stops29h 09m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:31 pm
ORF
- SFB
1 stop13h 00m
Multiple Airlines
Sun 8/166:35 am
SFB
- ORF
2 stops24h 56m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 6/811:25 am
ORF
- SFB
1 stop12h 10m
Multiple Airlines
Mon 6/151:16 pm
SFB
- ORF
2 stops9h 32m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$403
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 30, 2026.
Discover carefully curated flight deals from Chesapeake to Orlando that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 30, 2026.
This Breeze Airways deal was found by Cheapflights users on 5/25. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:00 am
ORF
- MCO
Nonstop2h 12m
Breeze Airways
Sat 7/410:00 am
MCO
- ORF
Nonstop2h 14m
Breeze Airways
Deal found 5/25![Breeze Airways logo]()
$218
This Southwest deal was found by Cheapflights users on 5/25. 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.
Tue 6/303:00 pm
ORF
- MCO
1 stop4h 35m
Southwest
Fri 7/33:30 pm
MCO
- ORF
2 stops8h 05m
Southwest
Deal found 5/25![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 5/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:17 pm
ORF
- MCO
1 stop6h 48m
Delta
Mon 7/207:55 pm
MCO
- ORF
1 stop4h 50m
Delta
Deal found 5/25![Delta logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 5/30. 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 7/3111:25 am
ORF
- SFB
1 stop12h 02m
Multiple Airlines
Sun 8/96:10 am
SFB
- ORF
2 stops29h 09m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$363
This United Airlines deal was found by Cheapflights users on 5/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:15 am
ORF
- MCO
2 stops8h 01m
United Airlines
Fri 8/217:40 am
MCO
- ORF
1 stop7h 37m
United Airlines
Deal found 5/27![United Airlines logo]()
$462
This Breeze Airways deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/57:00 am
ORF
- MCO
Nonstop2h 12m
Breeze Airways
Sat 7/117:27 pm
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 5/29![Breeze Airways logo]()
$253
This Southwest deal was found by Cheapflights users on 5/27. 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.
Thu 7/96:00 am
ORF
- MCO
2 stops7h 15m
Southwest
Tue 7/148:00 am
MCO
- ORF
2 stops6h 25m
Southwest
Deal found 5/27![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 5/28. 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 7/47:10 am
ORF
- MCO
2 stops8h 25m
Southwest
Thu 7/95:05 pm
MCO
- ORF
1 stop6h 35m
Southwest
Deal found 5/28![Southwest logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:31 pm
ORF
- SFB
1 stop13h 00m
Multiple Airlines
Sun 8/166:35 am
SFB
- ORF
2 stops24h 56m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:05 am
ORF
- MCO
2 stops8h 00m
Southwest
Sun 7/125:25 pm
MCO
- ORF
1 stop6h 00m
Southwest
Deal found 5/29![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 5/30. 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.
Thu 8/133:45 pm
ORF
- MCO
1 stop5h 15m
Southwest
Mon 8/171:30 pm
MCO
- ORF
2 stops8h 05m
Southwest
Deal found 5/30![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 5/27. 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.
Sun 8/163:15 pm
ORF
- MCO
2 stops8h 20m
Southwest
Fri 8/217:50 am
MCO
- ORF
1 stop4h 40m
Southwest
Deal found 5/27![Southwest logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Fri 6/1211:25 am
ORF
- SFB
1 stop12h 10m
Multiple Airlines
Tue 6/1612:42 pm
SFB
- ORF
2 stops46h 44m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$469
This Southwest deal was found by Cheapflights users on 5/30. 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.
Thu 7/26:00 am
ORF
- MCO
2 stops7h 00m
Southwest
Tue 7/73:10 pm
MCO
- ORF
2 stops7h 30m
Southwest
Deal found 5/30![Southwest logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:25 am
ORF
- SFB
1 stop12h 02m
Multiple Airlines
Sun 7/126:15 am
SFB
- ORF
2 stops10h 58m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$479
This Southwest deal was found by Cheapflights users on 5/25. 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.
Thu 6/259:55 am
ORF
- MCO
2 stops8h 05m
Southwest
Sat 6/274:10 pm
MCO
- ORF
2 stops6h 55m
Southwest
Deal found 5/25![Southwest logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/197:00 am
ORF
- SFB
2 stops9h 38m
Multiple Airlines
Sun 6/218:58 am
SFB
- ORF
1 stop25h 42m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$575
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:31 pm
ORF
- SFB
1 stop13h 00m
Multiple Airlines
Tue 8/181:55 pm
SFB
- ORF
2 stops45h 31m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$628
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Fri 6/2611:25 am
ORF
- SFB
1 stop12h 05m
Multiple Airlines
Sun 6/288:58 am
SFB
- ORF
2 stops7h 49m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$743
Last-minute flights from Chesapeake to OrlandoDiscover last-minute flight deals from Chesapeake to Orlando. Data last updated May 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Orlando. Data last updated May 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
ORF
- SFB
2 stops16h 29m
Multiple Airlines
Sun 6/79:13 pm
SFB
- ORF
1 stop13h 27m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$489
This Super.com deal was found by Cheapflights users on 5/25. 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.
Fri 6/59:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Mon 6/86:11 pm
MCO
- ORF
Nonstop2h 06m
Frontier
Deal found 5/25![Frontier logo]()
$157
This Super.com deal was found by Cheapflights users on 5/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Fri 6/126:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/29![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 6/55:24 pm
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Mon 6/88:20 pm
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 5/27![Breeze Airways logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 5/26. 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.
Fri 6/511:25 am
ORF
- SFB
1 stop12h 10m
Multiple Airlines
Sun 6/79:13 pm
SFB
- ORF
1 stop13h 27m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$512
This Super.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Wed 6/174:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/26![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Tue 6/164:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/26![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/89:12 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Wed 6/174:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/29![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 6/811:25 am
ORF
- SFB
1 stop12h 10m
Multiple Airlines
Mon 6/151:16 pm
SFB
- ORF
2 stops9h 32m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Fri 6/1211:25 am
ORF
- SFB
1 stop12h 10m
Multiple Airlines
Tue 6/1612:42 pm
SFB
- ORF
2 stops46h 44m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$469
This Frontier deal was found by Cheapflights users on 5/25. 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 6/247:35 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Sat 7/44:58 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/25![Frontier logo]()
$165
This Frontier deal was found by Cheapflights users on 5/27. 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.
Tue 6/307:25 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Sat 7/44:58 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 5/27![Frontier logo]()
$163
One-way flights from Chesapeake to OrlandoSearch for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated May 30, 2026.
Search for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated May 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:00 am
ORF
- MCO
Nonstop2h 12m
Breeze Airways
Deal found 5/26![Breeze Airways logo]()
$68
This Frontier deal was found by Cheapflights users on 5/28. 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.
Sun 8/239:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 5/28![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 5/26. 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 7/257:00 am
ORF
- MCO
Nonstop2h 20m
Breeze Airways
Deal found 5/26![Breeze Airways logo]()
$78
This Frontier deal was found by Cheapflights users on 5/27. 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 7/259:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 5/27![Frontier logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 6/55:24 pm
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Deal found 5/27![Breeze Airways logo]()
$83
This Frontier deal was found by Cheapflights users on 5/28. 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 8/259:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 5/28![Frontier logo]()
$84
This Super.com deal was found by Cheapflights users on 5/25. 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.
Wed 6/247:35 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 5/25![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 5/30. 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 8/2412:04 pm
ORF
- MCO
Nonstop2h 16m
Breeze Airways
Deal found 5/30![Breeze Airways logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 5/30. 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.
Wed 7/2210:31 pm
ORF
- SFB
1 stop13h 05m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 5/26. 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.
Wed 8/1210:31 pm
ORF
- SFB
1 stop13h 00m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 5/28. 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
Deal found 5/28![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 5/30. 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.
Wed 7/1510:31 pm
ORF
- SFB
1 stop13h 05m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$167
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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $152 (Kiwi.com) |
One-way from | $68 (Kiwi.com) |
Popular in | April |
Cheapest in | February |
Average price | $163 |
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 30, 2026.
Use the filters below to find and compare flights from Chesapeake to Orlando that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Thu 7/2
7:00 am-9:12 am
Nonstop2h 12m
Orlando
Sat 7/4
10:00 am-12:14 pm
Nonstop2h 14m
$218
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sun 7/5
7:00 am-9:12 am
Nonstop2h 12m
Orlando
Sat 7/11
7:27 pm-9:45 pm
Nonstop2h 18m
$253
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Tue 6/30
3:00 pm-7:35 pm
1 stop4h 35m
Orlando
Fri 7/3
3:30 pm-11:35 pm
2 stops8h 05m
$292
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Thu 7/9
6:00 am-1:15 pm
2 stops7h 15m
Orlando
Tue 7/14
8:00 am-2:25 pm
2 stops6h 25m
$297
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sat 7/4
7:10 am-3:35 pm
2 stops8h 25m
Orlando
Thu 7/9
5:05 pm-11:40 pm
1 stop6h 35m
$300
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Wed 7/8
6:05 am-2:05 pm
2 stops8h 00m
Orlando
Sun 7/12
5:25 pm-11:25 pm
1 stop6h 00m
$314
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Thu 7/16
6:17 pm-1:05 am
1 stop6h 48m
Orlando
Mon 7/20
7:55 pm-12:45 am
1 stop4h 50m
$327
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Thu 8/13
3:45 pm-9:00 pm
1 stop5h 15m
Orlando
Mon 8/17
1:30 pm-9:35 pm
2 stops8h 05m
$331
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Sun 8/16
3:15 pm-11:35 pm
2 stops8h 20m
Orlando
Fri 8/21
7:50 am-12:30 pm
1 stop4h 40m
$332
NorfolkOrlando
ORF - MCO
ORFMCO
Norfolk
Thu 7/2
6:00 am-1:00 pm
2 stops7h 00m
Orlando
Tue 7/7
3:10 pm-10:40 pm
2 stops7h 30m
$342
Showing 1-10 of 36 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 30, 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.
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 May 23, 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. Thursday 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 May 30, 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
6.7
Crew
8.7
Boarding
8.3
Entertainment
6.7
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Crew
8.7
Boarding
8.3
Entertainment
6.7
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Crew
8.7
Boarding
8.3
Entertainment
6.7
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Crew
8.7
Boarding
8.3
Entertainment
6.7
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Spirit Airlines
Food
6.7
Crew
8.7
Boarding
8.3
Entertainment
6.7
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Crew
8.7
Boarding
8.3
Entertainment
6.7
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
Find useful and relevant information for your journey from Chesapeake to Orlando. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chesapeake to Orlando
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Complete your trip
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Search flights from Chesapeake to Orlando by cabin class
Find flights from Chesapeake to Orlando, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Orlando
Explore flights to Orlando departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 30, 2026.
Chesapeake and Orlando flights
Browse other Chesapeake and Orlando flight options. Last updated on May 30, 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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$43 | Average$129 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$55 | Average$123 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$328 | 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$103 | Average$236 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$103 | Average$239 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$437 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$161 | Average$333 | FlexibilityNo cancel fee | On-time71% |