$44+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — RIC
Jul 4 — Jul 111
Round-trip
1 adult, Economy
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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
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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.Cheap flight deals from Orlando to Chesapeake
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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 4, 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 4, 2026.
This Priceline deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Mon 8/249:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 6/3![Frontier logo]()
$88
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/244:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Tue 6/307:25 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$96
This Priceline deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sat 7/259:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$98
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/244:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Mon 6/299:35 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 6/3![Frontier logo]()
$103
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Mon 8/109:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:46 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Sat 8/299:56 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 6/2![Frontier logo]()
$114
This Expedia deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sat 7/189:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sat 8/19:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/244:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Wed 7/89:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Wed 7/299:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/2![Frontier logo]()
$123
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Tue 7/219:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$127
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 4, 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 4, 2026.
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:55 am
MCO
- ORF
1 stop5h 05m
Southwest
Tue 6/304:30 pm
ORF
- MCO
1 stop4h 15m
Southwest
Deal found 5/31![Southwest logo]()
$281
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/277:55 pm
MCO
- ORF
1 stop4h 50m
Delta
Mon 8/36:14 pm
ORF
- MCO
1 stop5h 50m
Delta
Deal found 5/30![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:35 am
MCO
- ORF
1 stop5h 15m
Southwest
Mon 7/134:30 pm
ORF
- MCO
2 stops8h 05m
Southwest
Deal found 6/1![Southwest logo]()
$300
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:05 am
MCO
- ORF
1 stop4h 40m
Delta
Sun 8/236:23 am
ORF
- MCO
1 stop4h 34m
Delta
Deal found 5/30![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:30 pm
MCO
- ORF
2 stops8h 05m
Southwest
Mon 8/241:55 pm
ORF
- MCO
1 stop5h 15m
Southwest
Deal found 6/3![Southwest logo]()
$304
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:55 pm
MCO
- ORF
1 stop4h 47m
Delta
Tue 7/712:33 pm
ORF
- MCO
1 stop5h 14m
Delta
Deal found 5/30![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:40 am
MCO
- ORF
1 stop4h 00m
Southwest
Wed 7/1511:40 am
ORF
- MCO
2 stops8h 15m
Southwest
Deal found 6/3![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/277:55 pm
MCO
- ORF
1 stop4h 50m
Delta
Fri 8/76:14 pm
ORF
- MCO
1 stop6h 50m
Delta
Deal found 5/30![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/163:30 pm
MCO
- ORF
2 stops8h 10m
Southwest
Tue 7/2110:05 am
ORF
- MCO
2 stops8h 00m
Southwest
Deal found 6/3![Southwest logo]()
$314
Last-minute flights from Orlando to ChesapeakeDiscover last-minute flight deals from Orlando to Chesapeake. Data last updated June 4, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Chesapeake. Data last updated June 4, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline 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 6/3![Frontier logo]()
$132
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/244:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Tue 6/307:25 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$96
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/244:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Mon 6/299:35 pm
ORF
- MCO
Nonstop2h 16m
Frontier
Deal found 6/3![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/244:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Wed 7/89:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$119
This Expedia deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sat 7/189:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sat 7/189:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/4![Frontier logo]()
$133
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Tue 7/219:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$127
This Flightnetwork deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sat 7/259:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$134
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Fri 7/249:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![Frontier logo]()
$98
This Frontier deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/236:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sun 7/269:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/4![Frontier logo]()
$128
This Frontier deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Wed 7/299:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/2![Frontier logo]()
$123
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Sat 8/19:34 pm
ORF
- MCO
Nonstop2h 13m
Frontier
Deal found 6/3![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 4, 2026.
Search for one-way flight options from Orlando to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 4, 2026.
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 6/3![Frontier logo]()
$44
This Frontier deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/304:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/2![Frontier logo]()
$48
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/3![Frontier logo]()
$57
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/3![Frontier logo]()
$59
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:29 pm
MCO
- ORF
Nonstop2h 10m
Frontier
Deal found 6/4![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:27 pm
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 5/31![Breeze Airways logo]()
$64
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/244:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/4![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:20 pm
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:00 am
MCO
- ORF
Nonstop2h 14m
Breeze Airways
Deal found 6/4![Breeze Airways logo]()
$78
This Orbitz deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/298:20 pm
MCO
- ORF
Nonstop2h 18m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$79
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:25 pm
MCO
- ORF
Nonstop2h 15m
Frontier
Deal found 6/3![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 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $88 (Priceline) |
One-way from | $44 (Super.com) |
Popular in | June |
Cheapest in | April |
Average price | $257 |
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 4, 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
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Wed 6/24
6:55 am-12:00 pm
1 stop5h 05m
Norfolk
Tue 6/30
4:30 pm-8:45 pm
1 stop4h 15m
$281
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Mon 7/27
7:55 pm-12:45 am
1 stop4h 50m
Norfolk
Mon 8/3
6:14 pm-12:04 am
1 stop5h 50m
$295
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Thu 7/9
9:35 am-2:50 pm
1 stop5h 15m
Norfolk
Mon 7/13
4:30 pm-12:35 am
2 stops8h 05m
$300
Quickest round-trip
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Wed 8/19
8:05 am-12:45 pm
1 stop4h 40m
Norfolk
Sun 8/23
6:23 am-10:57 am
1 stop4h 34m
$304
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Thu 8/20
1:30 pm-9:35 pm
2 stops8h 05m
Norfolk
Mon 8/24
1:55 pm-7:10 pm
1 stop5h 15m
$304
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Fri 7/3
7:55 pm-12:42 am
1 stop4h 47m
Norfolk
Tue 7/7
12:33 pm-5:47 pm
1 stop5h 14m
$304
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Fri 7/10
7:40 am-11:40 am
1 stop4h 00m
Norfolk
Wed 7/15
11:40 am-7:55 pm
2 stops8h 15m
$309
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Mon 7/27
7:55 pm-12:45 am
1 stop4h 50m
Norfolk
Fri 8/7
6:14 pm-1:04 am
1 stop6h 50m
$311
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Thu 7/16
3:30 pm-11:40 pm
2 stops8h 10m
Norfolk
Tue 7/21
10:05 am-6:05 pm
2 stops8h 00m
$314
Cheapest one-way
OrlandoNorfolk
MCO - ORF
MCOORF
Orlando
Fri 8/28
6:15 am-12:45 pm
1 stop6h 30m
$108
Showing 1-10 of 21 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 4, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 39% 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 May 30, 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 4, 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.
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.3
Overall
8.2
Crew
8.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.3
Overall
8.2
Crew
8.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.3
Overall
8.2
Crew
8.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.3
Overall
8.2
Crew
8.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.3
Overall
8.2
Crew
8.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.7
Comfort
8.2
Entertainment
6.7
Boarding
8.3
Overall
8.2
Crew
8.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
Find useful and relevant information for your journey from Orlando to Chesapeake. 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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Complete your trip
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Orlando and Chesapeake flights
Browse other Orlando and Chesapeake flight options. Last updated on June 4, 2026.
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Browse through other flights departing from Orlando. Flights are based on user searches made on Cheapflights and were last updated on June 4, 2026.
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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 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$133 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$279 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$83 | Average$204 | 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% |