$76+ Cheap flights from Chesapeake, VA to Orlando (ORL)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Sep 12 — Sep 191
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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in February or May, booked 86 days in advance, depart on a Sunday or Saturday and return on a Thursday
Cheap flight deals from Chesapeake to Orlando
Cheapest
Best
Last-minute
One-way
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 August 13, 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 August 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/101:18 pm -
1 stop8h 41m
Thu 9/176:50 am -
1 stop5h 39m
Deal found 8/11![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:20 pm -
1 stop8h 54m
Tue 9/85:24 am -
1 stop7h 01m
Deal found 8/11![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:18 pm -
1 stop8h 41m
Mon 10/54:44 pm -
Nonstop2h 04m
Deal found 8/11![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 8/307:00 am -
Nonstop2h 12m
Thu 9/244:44 pm -
Nonstop2h 04m
Deal found 8/12![Multiple Airlines logo]()
$137
This Priceline deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 8/235:06 pm -
Nonstop2h 11m
Wed 8/262:03 pm -
Nonstop2h 08m
Deal found 8/9![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 8/245:06 pm -
Nonstop2h 11m
Sat 8/295:23 pm -
1 stop19h 02m
Deal found 8/9![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:06 pm -
Nonstop2h 11m
Wed 9/25:23 pm -
1 stop19h 02m
Deal found 8/9![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:00 am -
Nonstop2h 12m
Mon 8/315:23 pm -
1 stop19h 02m
Deal found 8/11![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/2412:57 pm -
1 stop9h 13m
Sat 10/313:12 pm -
Nonstop2h 03m
Deal found 8/10![Frontier logo]()
$142
This Priceline deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:06 pm -
Nonstop2h 11m
Fri 9/42:03 pm -
Nonstop2h 08m
Deal found 8/11![Frontier logo]()
$143
This Frontier deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:06 pm -
Nonstop2h 11m
Tue 9/12:03 pm -
Nonstop2h 08m
Deal found 8/8![Frontier logo]()
$144
This Frontier deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:18 pm -
1 stop8h 41m
Sun 9/204:44 pm -
Nonstop2h 04m
Deal found 8/11![Frontier logo]()
$145
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 August 13, 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 August 13, 2026.
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:55 am -
1 stop7h 30m
Wed 9/302:05 pm -
2 stops6h 50m
Deal found 8/11![Southwest logo]()
$214
This Breeze Airways deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 12/36:00 am -
Nonstop2h 16m
Tue 12/812:57 pm -
Nonstop2h 07m
Deal found 8/12![Breeze Airways logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 8/236:00 am -
2 stops11h 05m
Thu 8/2710:00 am -
1 stop24h 40m
Deal found 8/8![Multiple Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/1412:30 pm -
2 stops9h 35m
Sat 10/178:50 am -
Nonstop1h 55m
Deal found 8/10![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:00 pm -
1 stop4h 25m
Sat 10/318:20 am -
2 stops8h 15m
Deal found 8/10![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:05 pm -
1 stop4h 10m
Mon 10/1210:35 pm -
1 stop10h 45m
Deal found 8/10![Southwest logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 11/57:30 am -
2 stops30h 24m
Thu 11/128:12 pm -
1 stop21h 20m
Deal found 8/9![Multiple Airlines logo]()
$370
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 11/15:55 pm -
1 stop7h 25m
Wed 11/48:50 am -
2 stops8h 35m
Deal found 8/10![Southwest logo]()
$279
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:20 am -
1 stop7h 00m
Sun 11/156:55 pm -
1 stop4h 35m
Deal found 8/12![Southwest logo]()
$280
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 11/183:05 pm -
2 stops8h 20m
Sun 11/229:05 am -
2 stops8h 10m
Deal found 8/11![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:45 pm -
2 stops7h 10m
Mon 9/144:10 pm -
1 stop5h 50m
Deal found 8/12![Southwest logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/174:57 pm -
1 stop24h 00m
Thu 9/2410:29 am -
1 stop24h 13m
Deal found 8/10![Multiple Airlines logo]()
$464
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:55 am -
2 stops7h 00m
Sun 9/137:55 am -
1 stop4h 40m
Deal found 8/12![Southwest logo]()
$303
Last-minute flights from Chesapeake to OrlandoDiscover last-minute flight deals from Chesapeake to Orlando. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Orlando. Data last updated August 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:06 am -
Nonstop2h 16m
Mon 8/247:23 pm -
Nonstop2h 18m
Deal found 8/10![Breeze Airways logo]()
$197
This CheapOair deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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.
Thu 8/205:06 pm -
Nonstop2h 11m
Sat 8/292:03 pm -
Nonstop2h 08m
Deal found 8/9![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:06 pm -
Nonstop2h 11m
Tue 8/255:24 am -
1 stop7h 01m
Deal found 8/9![Frontier logo]()
$192
This CheapOair deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Thu 8/207:00 am -
Nonstop2h 12m
Sat 8/297:27 pm -
Nonstop2h 18m
Deal found 8/11![Breeze Airways logo]()
$198
This Frontier deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:06 pm -
Nonstop2h 11m
Sun 8/232:03 pm -
Nonstop2h 08m
Deal found 8/9![Frontier logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:06 pm -
Nonstop2h 11m
Tue 8/255:24 am -
1 stop7h 01m
Deal found 8/8![Frontier logo]()
$179
This Priceline deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 8/235:06 pm -
Nonstop2h 11m
Wed 8/262:03 pm -
Nonstop2h 08m
Deal found 8/9![Frontier logo]()
$138
This CheapOair deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:06 pm -
Nonstop2h 11m
Fri 8/282:03 pm -
Nonstop2h 08m
Deal found 8/11![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 8/236:00 am -
2 stops11h 05m
Thu 8/2710:00 am -
1 stop24h 40m
Deal found 8/8![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/174:57 pm -
1 stop24h 00m
Thu 9/248:23 pm -
2 stops43h 27m
Deal found 8/10![Multiple Airlines logo]()
$403
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 August 13, 2026.
Search for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This Super.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/55:06 pm -
Nonstop2h 11m
Deal found 8/8![Frontier logo]()
$76
This Super.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Thu 8/275:06 pm -
Nonstop2h 11m
Deal found 8/11![Frontier logo]()
$77
This Frontier deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 11/76:10 pm -
Nonstop2h 13m
Deal found 8/11![Frontier logo]()
$79
This CheapOair deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Thu 8/277:00 am -
Nonstop2h 12m
Deal found 8/11![Breeze Airways logo]()
$81
This Super.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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.
Thu 10/81:19 pm -
1 stop6h 33m
Deal found 8/13![Frontier logo]()
$82
This Super.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/1012:57 pm -
1 stop9h 13m
Deal found 8/11![Frontier logo]()
$87
This Super.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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.
Thu 11/1212:57 pm -
1 stop9h 13m
Deal found 8/13![Frontier logo]()
$88
This Breeze Airways deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 8/307:00 am -
Nonstop2h 12m
Deal found 8/11![Breeze Airways logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 11/212:57 pm -
2 stops45h 08m
Deal found 8/8![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 8/1910:31 pm -
1 stop20h 12m
Deal found 8/11![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 8/306:00 am -
2 stops13h 35m
Deal found 8/12![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/101:18 pm -
3 stops27h 05m
Deal found 8/12![Multiple Airlines logo]()
$169
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 August 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $134 (Kiwi.com) |
One-way from | $76 (Super.com) |
Popular in | April |
Cheapest in | February |
Average price | $185 |
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 August 13, 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 Norfolk - MCO Orlando
ORFMCO
Norfolk
Sat 9/26
9:55 am-5:25 pm
1 stop7h 30m
Orlando
Wed 9/30
2:05 pm-8:55 pm
2 stops6h 50m
$214
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Wed 10/14
12:30 pm-10:05 pm
2 stops9h 35m
Orlando
Sat 10/17
8:50 am-10:45 am
Nonstop1h 55m
$218
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Sat 10/24
4:00 pm-8:25 pm
1 stop4h 25m
Orlando
Sat 10/31
8:20 am-4:35 pm
2 stops8h 15m
$228
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Fri 10/9
6:05 pm-10:15 pm
1 stop4h 10m
Orlando
Mon 10/12
10:35 pm-9:20 am
1 stop10h 45m
$257
Quickest round-trip
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Thu 12/3
6:00 am-8:16 am
Nonstop2h 16m
Orlando
Tue 12/8
12:57 pm-3:04 pm
Nonstop2h 07m
$278
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Sun 11/1
5:55 pm-1:20 am
1 stop7h 25m
Orlando
Wed 11/4
8:50 am-5:25 pm
2 stops8h 35m
$279
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Sat 11/7
10:20 am-5:20 pm
1 stop7h 00m
Orlando
Sun 11/15
6:55 pm-11:30 pm
1 stop4h 35m
$280
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Wed 11/18
3:05 pm-11:25 pm
2 stops8h 20m
Orlando
Sun 11/22
9:05 am-5:15 pm
2 stops8h 10m
$283
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Fri 9/11
3:45 pm-10:55 pm
2 stops7h 10m
Orlando
Mon 9/14
4:10 pm-10:00 pm
1 stop5h 50m
$285
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Sat 9/12
9:55 am-4:55 pm
2 stops7h 00m
Orlando
Sun 9/13
7:55 am-12:35 pm
1 stop4h 40m
$303
Showing 1-10 of 31 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 August 13, 2026.
It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 40% on the flight price compared to flying at noon, which is usually more expensive.
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 August 13, 2026.
The most flights from C6E to ORL are scheduled on a Wednesday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Chesapeake to Orlando?
Airfare is below average for this route at the moment.
Chesapeake to Orlando flights typically cost between $144 and $292 in September.The cheapest round-trip price found within the last 5 days was $134 on Frontier (Sep 10-Sep 17).
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 August 8, 2026.
Travelers seeking maximum savings on their Chesapeake to Orlando flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Orlando
Get insights into the airlines that provide service to Orlando. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Orlando. Reviews last updated August 13, 2026.
Peruse reviews from past customers who have flown with Breeze Airways,Southwest, andDelta from Chesapeake to Orlando to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.3
Comfort
8.2
Food
6.7
Overall
8.2
Crew
8.7
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Food
6.7
Overall
8.2
Crew
8.7
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Food
6.7
Overall
8.2
Crew
8.7
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Food
6.7
Overall
8.2
Crew
8.7
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Food
6.7
Overall
8.2
Crew
8.7
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Food
6.7
Overall
8.2
Crew
8.7
Entertainment
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
Find useful and relevant information for your journey from Chesapeake to Orlando. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Top 8 airlines flying from Chesapeake to Orlando
Discover the top 8 airlines that operate flights from Chesapeake to Orlando. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$159 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$291 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$98 | Average$210 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$99 | Average$318 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$249 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$109 | Average$249 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$158 | Average$361 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$558 | FlexibilityNo cancel fee | On-time69% |