$54+ Cheap flights from Orlando (ORL) to Chesapeake, VA
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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — RIC
Jul 11 — Jul 181
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Orlando to Chesapeake 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.Cheap flight deals from Orlando to Chesapeake
Cheapest
Best
Last-minute
One-way
Cheapest flights from Orlando to ChesapeakeExplore the most affordable flight options available from Orlando to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 11, 2026.
Explore the most affordable flight options available from Orlando to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 11, 2026.
This Frontier deal was found by Cheapflights users on 6/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Wed 9/29:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 6/10![Frontier logo]()
$108
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 8/156:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sun 8/239:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 6/7![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 8/136:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Mon 8/179:53 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/236:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Thu 7/309:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/226:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Wed 7/299:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$123
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/166:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Thu 7/239:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$127
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/176:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sun 7/199:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$128
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/156:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sat 7/189:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$133
This Frontier deal was found by Cheapflights users on 6/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Mon 8/109:53 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/10![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 7/306:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Wed 8/59:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/11![Frontier logo]()
$142
This Frontier deal was found by Cheapflights users on 6/8. 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.
Thu 8/66:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Mon 8/109:53 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/8![Frontier logo]()
$146
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 8/296:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Fri 9/49:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 6/7![Frontier logo]()
$147
Best flights from Orlando to ChesapeakeDiscover carefully curated flight deals from Orlando to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 11, 2026.
Discover carefully curated flight deals from Orlando to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 11, 2026.
This Breeze Airways deal was found by Cheapflights users on 6/9. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:27 pm
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Sun 7/267:00 am
ORF
- MCO
Nonstop2h 12m
Breeze Airways
Deal found 6/9![Breeze Airways logo]()
$218
This Southwest deal was found by Cheapflights users on 6/11. 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.
Mon 8/241:30 pm
MCO
- ORF
2 stops8h 05m
Southwest
Sat 8/2912:25 pm
ORF
- MCO
1 stop7h 00m
Southwest
Deal found 6/11![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:55 pm
MCO
- ORF
1 stop4h 50m
Delta
Mon 7/276:17 pm
ORF
- MCO
1 stop5h 41m
Delta
Deal found 6/10![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 6/10. 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 7/173:30 pm
MCO
- ORF
2 stops8h 10m
Southwest
Tue 7/2112:25 pm
ORF
- MCO
2 stops7h 05m
Southwest
Deal found 6/10![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/246:52 pm
MCO
- ORF
1 stop5h 53m
Delta
Mon 7/276:17 pm
ORF
- MCO
1 stop5h 41m
Delta
Deal found 6/8![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 8/268:35 am
MCO
- ORF
2 stops7h 20m
Southwest
Sat 8/296:25 am
ORF
- MCO
2 stops7h 50m
Southwest
Deal found 6/7![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 6/10. 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 7/185:15 pm
MCO
- ORF
1 stop5h 55m
Southwest
Sat 7/259:55 am
ORF
- MCO
2 stops5h 50m
Southwest
Deal found 6/10![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 8/18:30 am
MCO
- ORF
1 stop6h 45m
Southwest
Sat 8/86:25 am
ORF
- MCO
2 stops6h 10m
Southwest
Deal found 6/7![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 6/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/173:30 pm
MCO
- ORF
2 stops8h 10m
Southwest
Fri 7/244:30 pm
ORF
- MCO
1 stop5h 45m
Southwest
Deal found 6/8![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 6/11. 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.
Thu 9/310:00 am
MCO
- ORF
2 stops7h 55m
Southwest
Mon 9/71:55 pm
ORF
- MCO
1 stop6h 15m
Southwest
Deal found 6/11![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 6/10. 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 7/19:55 pm
MCO
- ORF
1 stop11h 25m
Southwest
Thu 7/1612:15 pm
ORF
- MCO
2 stops7h 30m
Southwest
Deal found 6/10![Southwest logo]()
$335
Last-minute flights from Orlando to ChesapeakeDiscover last-minute flight deals from Orlando to Chesapeake. Data last updated June 11, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Chesapeake. Data last updated June 11, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/174:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Wed 6/247:35 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$153
This Frontier deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 6/244:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Tue 6/307:25 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/6![Frontier logo]()
$138
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/86:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Tue 7/149:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$148
This Super.com deal was found by Cheapflights users on 6/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sat 7/119:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/10![Frontier logo]()
$164
This Frontier deal was found by Cheapflights users on 6/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Tue 7/149:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/10![Frontier logo]()
$165
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/116:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Wed 7/159:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$162
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/156:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sat 7/189:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$133
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/166:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Thu 7/239:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$127
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/176:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sun 7/199:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$128
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/226:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Wed 7/299:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$123
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/236:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Thu 7/309:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/306:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sun 8/29:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/7![Frontier logo]()
$118
One-way flights from Orlando to ChesapeakeSearch for one-way flight options from Orlando to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
Search for one-way flight options from Orlando to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
This Frontier deal was found by Cheapflights users on 6/11. 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.
Wed 8/56:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/11![Frontier logo]()
$54
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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.
Tue 8/46:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/7![Frontier logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 8/69:52 am
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 6/11![Breeze Airways logo]()
$63
This Frontier deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 9/56:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/7![Frontier logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 8/16:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/8![Frontier logo]()
$68
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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.
Tue 6/304:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/7![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/99:52 am
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 6/10![Breeze Airways logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/410:00 am
MCO
- ORF
Nonstop2h 14m
Breeze Airways
Deal found 6/10![Breeze Airways logo]()
$78
This Expedia deal was found by Cheapflights users on 6/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/44:58 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/9![Frontier logo]()
$79
This Super.com deal was found by Cheapflights users on 6/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/10![Frontier logo]()
$81
This Frontier deal was found by Cheapflights users on 6/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/10![Frontier logo]()
$82
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/174:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/7![Frontier logo]()
$83
Find flight deals from Orlando to Chesapeake
Keep the following information in mind while searching for Orlando to Chesapeake flight deals. Data was last updated June 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $108 (Frontier) |
One-way from | $54 (Frontier) |
Popular in | June |
Cheapest in | April |
Average price | $255 |
Cheapflights Fare Finder
Customize your flight search to find flights from Orlando to Chesapeake 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 June 11, 2026.
Use the filters below to find and compare flights from Orlando to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Wed 7/22
7:27 pm-9:45 pm
Nonstop2h 18m
Norfolk
Sun 7/26
7:00 am-9:12 am
Nonstop2h 12m
$218
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Mon 8/24
1:30 pm-9:35 pm
2 stops8h 05m
Norfolk
Sat 8/29
12:25 pm-7:25 pm
1 stop7h 00m
$256
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Fri 7/17
3:30 pm-11:40 pm
2 stops8h 10m
Norfolk
Tue 7/21
12:25 pm-7:30 pm
2 stops7h 05m
$319
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Thu 7/23
7:55 pm-12:45 am
1 stop4h 50m
Norfolk
Mon 7/27
6:17 pm-11:58 pm
1 stop5h 41m
$327
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Fri 7/24
6:52 pm-12:45 am
1 stop5h 53m
Norfolk
Mon 7/27
6:17 pm-11:58 pm
1 stop5h 41m
$327
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Wed 8/26
8:35 am-3:55 pm
2 stops7h 20m
Norfolk
Sat 8/29
6:25 am-2:15 pm
2 stops7h 50m
$327
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Sat 7/18
5:15 pm-11:10 pm
1 stop5h 55m
Norfolk
Sat 7/25
9:55 am-3:45 pm
2 stops5h 50m
$329
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Sat 8/1
8:30 am-3:15 pm
1 stop6h 45m
Norfolk
Sat 8/8
6:25 am-12:35 pm
2 stops6h 10m
$332
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Fri 7/17
3:30 pm-11:40 pm
2 stops8h 10m
Norfolk
Fri 7/24
4:30 pm-10:15 pm
1 stop5h 45m
$332
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Thu 9/3
10:00 am-5:55 pm
2 stops7h 55m
Norfolk
Mon 9/7
1:55 pm-8:10 pm
1 stop6h 15m
$332
Showing 1-10 of 22 resultsSorted by cheapest first
Best time to book a flight from Orlando to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Orlando with our price prediction graph.
MCO-ORF
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 Orlando to Chesapeake
ORL-C6E
MCO-ORF
What is the cheapest time of day to fly from ORL to C6E?
Find hourly flight availability from Orlando to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 11, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 38% on flights from Orlando to Chesapeake by exploring options for tickets in the afternoon.
How much does it cost to fly round-trip from Orlando to Chesapeake?
What is the cheapest day to fly from Orlando to Chesapeake?
Use this chart to determine the cheapest time to fly round-trip from Orlando to Chesapeake. Price data was last updated on June 8, 2026.
Travelers seeking maximum savings on their Orlando to Chesapeake flight should consider departing on Monday mornings when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chesapeake
Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated June 11, 2026.
Get a feel of what it's like to fly with Breeze Airways,Southwest, andDelta from Orlando to Chesapeake by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.7
Crew
8.7
Food
6.7
Boarding
8.3
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.7
Crew
8.7
Food
6.7
Boarding
8.3
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.7
Crew
8.7
Food
6.7
Boarding
8.3
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.7
Crew
8.7
Food
6.7
Boarding
8.3
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.7
Crew
8.7
Food
6.7
Boarding
8.3
Comfort
8.2
Overall
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.7
Crew
8.7
Food
6.7
Boarding
8.3
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 Orlando to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Orlando
Popular flights
Alternative routes for Orlando to Chesapeake
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Orlando to Chesapeake by cabin class
Find flights from Orlando to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Orlando and Chesapeake flights
Browse other Orlando and Chesapeake flight options. Last updated on June 11, 2026.
Other flights from Orlando
Browse through other flights departing from Orlando. Flights are based on user searches made on Cheapflights and were last updated on June 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Orlando to Chesapeake
Discover the top 7 airlines that operate flights from Orlando to Chesapeake. 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 June 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$134 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$281 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$83 | Average$207 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$84 | Average$108 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$88 | Average$317 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$108 | Average$173 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$158 | Average$323 | FlexibilityNo cancel fee | On-time71% |