$74+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Sep 26 — Oct 31
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 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 27, 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 27, 2026.
This Super.com deal was found by Cheapflights users on 8/27. 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.
Wed 10/217:41 pm -
Nonstop2h 13m
Wed 10/284:44 pm -
Nonstop2h 00m
Deal found 8/27![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 10/243:50 pm -
1 stop5h 40m
Thu 10/296:07 am -
1 stop6h 39m
Deal found 8/26![Frontier logo]()
$132
This Trip.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Sat 9/127:43 pm -
Nonstop2h 12m
Wed 9/164:44 pm -
Nonstop2h 04m
Deal found 8/23![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:43 pm -
Nonstop2h 12m
Thu 9/176:50 am -
1 stop5h 39m
Deal found 8/23![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:45 pm -
1 stop5h 14m
Sat 10/34:44 pm -
Nonstop2h 04m
Deal found 8/27![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:18 pm -
1 stop8h 41m
Sun 10/46:50 am -
1 stop5h 39m
Deal found 8/24![Frontier logo]()
$137
This CheapOair deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Fri 9/117:43 pm -
Nonstop2h 12m
Tue 9/154:44 pm -
Nonstop2h 04m
Deal found 8/23![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Tue 11/177:41 pm -
Nonstop2h 15m
Thu 11/269:55 am -
Nonstop2h 00m
Deal found 8/25![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/137:43 pm -
Nonstop2h 12m
Thu 9/176:50 am -
1 stop5h 39m
Deal found 8/26![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:18 pm -
1 stop8h 41m
Wed 9/304:44 pm -
Nonstop2h 04m
Deal found 8/24![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/136:00 am -
Nonstop2h 16m
Thu 9/1712:57 pm -
Nonstop2h 07m
Deal found 8/26![Breeze Airways logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Thu 10/19:50 pm -
2 stops14h 32m
Sun 10/47:31 pm -
1 stop15h 11m
Deal found 8/25![Multiple Airlines logo]()
$568
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 27, 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 27, 2026.
This Breeze Airways deal was found by Cheapflights users on 8/25. 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.
Wed 11/1812:07 pm -
Nonstop2h 16m
Fri 11/2010:07 am -
1 stop9h 16m
Deal found 8/25![Breeze Airways logo]()
$223
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:05 pm -
1 stop4h 20m
Sat 11/219:00 pm -
Nonstop2h 00m
Deal found 8/24![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 8/25. 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.
Sat 12/55:27 pm -
1 stop7h 13m
Wed 12/97:45 am -
1 stop6h 09m
Deal found 8/25![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/179:55 am -
1 stop6h 00m
Mon 2/229:05 am -
Nonstop2h 00m
Deal found 8/26![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:15 am -
2 stops8h 45m
Wed 9/302:05 pm -
2 stops6h 50m
Deal found 8/24![Southwest logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/286:12 pm -
1 stop14h 34m
Sun 1/36:20 am -
1 stop14h 25m
Deal found 8/26![Multiple Airlines logo]()
$592
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/163:05 pm -
2 stops8h 20m
Thu 11/1911:10 am -
2 stops6h 15m
Deal found 8/26![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/154:10 pm -
1 stop5h 40m
Fri 2/198:15 am -
1 stop4h 30m
Deal found 8/23![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/108:00 am -
2 stops9h 00m
Sat 11/213:15 pm -
2 stops8h 10m
Deal found 8/24![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:00 pm -
2 stops6h 55m
Thu 10/292:50 pm -
2 stops6h 35m
Deal found 8/26![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/25. 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 2/167:40 am -
2 stops7h 00m
Fri 2/198:50 pm -
Nonstop2h 05m
Deal found 8/25![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:00 am -
2 stops7h 05m
Mon 11/236:30 am -
2 stops8h 15m
Deal found 8/24![Southwest logo]()
$287
Last-minute flights from Chesapeake to OrlandoDiscover last-minute flight deals from Chesapeake to Orlando. Data last updated August 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Orlando. Data last updated August 27, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Fri 9/117:43 pm -
Nonstop2h 12m
Tue 9/154:44 pm -
Nonstop2h 04m
Deal found 8/23![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/117:43 pm -
Nonstop2h 12m
Mon 9/149:30 am -
1 stop26h 59m
Deal found 8/23![Frontier logo]()
$144
This Trip.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Sat 9/127:43 pm -
Nonstop2h 12m
Wed 9/164:44 pm -
Nonstop2h 04m
Deal found 8/23![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/137:43 pm -
Nonstop2h 12m
Thu 9/176:50 am -
1 stop5h 39m
Deal found 8/26![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/136:00 am -
Nonstop2h 16m
Thu 9/1712:57 pm -
Nonstop2h 07m
Deal found 8/26![Breeze Airways logo]()
$142
This Priceline deal was found by Cheapflights users on 8/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:43 pm -
Nonstop2h 12m
Tue 9/154:44 pm -
Nonstop2h 04m
Deal found 8/26![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:43 pm -
Nonstop2h 12m
Thu 9/176:50 am -
1 stop5h 39m
Deal found 8/23![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:18 pm -
1 stop8h 41m
Wed 9/234:44 pm -
Nonstop2h 04m
Deal found 8/24![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:18 pm -
1 stop8h 41m
Sun 10/46:50 am -
1 stop5h 39m
Deal found 8/24![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:45 pm -
1 stop5h 14m
Sat 10/34:44 pm -
Nonstop2h 04m
Deal found 8/27![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:18 pm -
1 stop8h 41m
Wed 9/304:44 pm -
Nonstop2h 04m
Deal found 8/24![Frontier logo]()
$141
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 27, 2026.
Search for one-way flight options from Chesapeake to Orlando. Find affordable one-way fares based on user searches. Data last updated August 27, 2026.
This Breeze Airways deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
Nonstop2h 16m
Deal found 8/24![Breeze Airways logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:43 pm -
Nonstop2h 12m
Deal found 8/23![Frontier logo]()
$75
This iWofly deal was found by Cheapflights users on 8/25. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
Nonstop2h 16m
Deal found 8/25![Breeze Airways logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/124:45 pm -
1 stop5h 14m
Deal found 8/22![Frontier logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/226:00 am -
Nonstop2h 16m
Deal found 8/26![Breeze Airways logo]()
$78
This Breeze Airways deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Tue 11/38:05 am -
Nonstop2h 16m
Deal found 8/23![Breeze Airways logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 10/248:00 am -
Nonstop2h 16m
Deal found 8/26![Breeze Airways logo]()
$83
This Frontier deal was found by Cheapflights users on 8/27. 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.
Wed 9/237:43 pm -
Nonstop2h 12m
Deal found 8/27![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/247:43 pm -
Nonstop2h 12m
Deal found 8/23![Frontier logo]()
$85
This CheapOair deal was found by Cheapflights users on 8/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
Nonstop2h 16m
Deal found 8/27![Breeze Airways logo]()
$86
This Jetabroad deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:43 pm -
Nonstop2h 12m
Deal found 8/24![Frontier logo]()
$87
This Super.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/197:43 pm -
Nonstop2h 12m
Deal found 8/22![Frontier logo]()
$88
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 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $131 (Super.com) |
One-way from | $74 (Breeze Airways) |
Popular in | April |
Cheapest in | February |
Average price | $183 |
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 7,457,451 searches. Data last updated August 27, 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
Wed 11/18
12:07 pm-2:23 pm
Nonstop2h 16m
Orlando
Fri 11/20
10:07 am-7:23 pm
1 stop9h 16m
$223
Quickest round-trip
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Wed 11/11
6:05 pm-10:25 pm
1 stop4h 20m
Orlando
Sat 11/21
9:00 pm-11:00 pm
Nonstop2h 00m
$242
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Wed 2/17
9:55 am-3:55 pm
1 stop6h 00m
Orlando
Mon 2/22
9:05 am-11:05 am
Nonstop2h 00m
$242
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Sat 12/5
5:27 pm-12:40 am
1 stop7h 13m
Orlando
Wed 12/9
7:45 am-1:54 pm
1 stop6h 09m
$247
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Tue 9/29
6:15 am-3:00 pm
2 stops8h 45m
Orlando
Wed 9/30
2:05 pm-8:55 pm
2 stops6h 50m
$257
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Mon 11/16
3:05 pm-11:25 pm
2 stops8h 20m
Orlando
Thu 11/19
11:10 am-5:25 pm
2 stops6h 15m
$268
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Mon 2/15
4:10 pm-9:50 pm
1 stop5h 40m
Orlando
Fri 2/19
8:15 am-12:45 pm
1 stop4h 30m
$287
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Tue 11/10
8:00 am-5:00 pm
2 stops9h 00m
Orlando
Sat 11/21
3:15 pm-11:25 pm
2 stops8h 10m
$287
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Sat 10/24
4:00 pm-10:55 pm
2 stops6h 55m
Orlando
Thu 10/29
2:50 pm-9:25 pm
2 stops6h 35m
$287
NorfolkOrlando
ORF Norfolk - MCO Orlando
ORFMCO
Norfolk
Tue 2/16
7:40 am-2:40 pm
2 stops7h 00m
Orlando
Fri 2/19
8:50 pm-10:55 pm
Nonstop2h 05m
$287
Showing 1-10 of 35 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 27, 2026.
It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 37% on the flight price compared to flying at noon, which is usually more expensive.
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 $147 and $280 in October.The cheapest round-trip price found within the last 5 days was $131 on Frontier (Oct 21-Oct 28).
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 22, 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 27, 2026.
Peruse reviews from past customers who have flown with Breeze Airways,Southwest, andDelta from Chesapeake to Orlando to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.8
Entertainment
6.7
Boarding
8.3
Food
6.7
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Entertainment
6.7
Boarding
8.3
Food
6.7
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Entertainment
6.7
Boarding
8.3
Food
6.7
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Entertainment
6.7
Boarding
8.3
Food
6.7
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Entertainment
6.7
Boarding
8.3
Food
6.7
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Entertainment
6.7
Boarding
8.3
Food
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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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 August 27, 2026.
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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 7,457,451 searches. Data last updated August 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$156 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$72 | Average$261 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$81 | Average$206 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$88 | Average$291 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$101 | Average$319 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$111 | Average$247 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$158 | Average$372 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$211 | Average$558 | FlexibilityNo cancel fee | On-time69% |