$53+ Cheap flights from Orlando (ORL) to Chesapeake, VA
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — RIC
Oct 22 — Oct 291
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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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 September 22, 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 September 22, 2026.
This Priceline deal was found by Cheapflights users on 9/20. 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 10/611:06 am -
Nonstop2h 07m
Tue 10/67:43 pm -
Nonstop2h 12m
Deal found 9/20![Multiple Airlines logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/74:44 pm -
Nonstop2h 04m
Sun 10/117:41 pm -
Nonstop2h 13m
Deal found 9/17![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 9/20. 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 11/79:25 am -
1 stop5h 29m
Sun 11/87:41 pm -
Nonstop2h 15m
Deal found 9/20![Frontier logo]()
$122
This Priceline deal was found by Cheapflights users on 9/17. 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.
Sat 10/1010:56 am -
Nonstop2h 07m
Sat 10/173:50 pm -
1 stop5h 40m
Deal found 9/17![Multiple Airlines logo]()
$124
This Super.com deal was found by Cheapflights users on 9/19. 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 10/64:44 pm -
Nonstop2h 04m
Sun 10/187:41 pm -
Nonstop2h 13m
Deal found 9/19![Frontier logo]()
$126
This CheapOair deal was found by Cheapflights users on 9/18. 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 10/296:07 am -
1 stop6h 39m
Tue 11/37:41 pm -
Nonstop2h 15m
Deal found 9/18![Frontier logo]()
$127
This Super.com deal was found by Cheapflights users on 9/21. 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 10/144:44 pm -
Nonstop2h 02m
Tue 10/207:41 pm -
Nonstop2h 13m
Deal found 9/21![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/212:57 pm -
Nonstop2h 07m
Tue 10/68:05 am -
Nonstop2h 16m
Deal found 9/17![Breeze Airways logo]()
$132
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/154:44 pm -
Nonstop2h 02m
Tue 10/201:19 pm -
1 stop8h 11m
Deal found 9/20![Frontier logo]()
$134
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:56 am -
1 stop6h 48m
Sun 10/117:41 pm -
Nonstop2h 13m
Deal found 9/17![Frontier logo]()
$135
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:44 pm -
Nonstop2h 02m
Sun 10/117:41 pm -
Nonstop2h 13m
Deal found 9/18![Frontier logo]()
$136
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 September 22, 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 September 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/144:53 pm -
1 stop19h 45m
Tue 10/201:19 pm -
1 stop8h 11m
Deal found 9/21![Frontier logo]()
$157
This Southwest deal was found by Cheapflights users on 9/21. 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 10/213:40 pm -
1 stop4h 15m
Wed 10/2812:30 pm -
2 stops8h 30m
Deal found 9/21![Southwest logo]()
$252
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:20 pm -
1 stop5h 28m
Mon 10/127:59 pm -
1 stop5h 00m
Deal found 9/21![United Airlines logo]()
$471
This Southwest deal was found by Cheapflights users on 9/17. 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 11/197:05 am -
1 stop7h 20m
Mon 11/236:15 am -
2 stops9h 15m
Deal found 9/17![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 9/21. 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 10/153:15 pm -
2 stops8h 25m
Tue 10/2012:30 pm -
2 stops8h 05m
Deal found 9/21![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 9/19. 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 11/213:15 pm -
2 stops8h 15m
Tue 11/246:00 am -
2 stops8h 15m
Deal found 9/19![Southwest logo]()
$389
This Southwest deal was found by Cheapflights users on 9/19. 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 11/267:25 am -
2 stops9h 05m
Mon 11/306:00 am -
2 stops8h 10m
Deal found 9/19![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 9/17. 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 11/286:15 am -
1 stop5h 15m
Tue 12/13:05 pm -
2 stops8h 25m
Deal found 9/17![Southwest logo]()
$444
This Southwest deal was found by Cheapflights users on 9/19. 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 11/2410:10 am -
2 stops8h 30m
Sat 11/289:40 am -
1 stop6h 10m
Deal found 9/19![Southwest logo]()
$444
This Southwest deal was found by Cheapflights users on 9/21. 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 11/213:15 pm -
2 stops8h 15m
Sat 11/286:00 am -
2 stops8h 40m
Deal found 9/21![Southwest logo]()
$449
This Southwest deal was found by Cheapflights users on 9/21. 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 11/2510:10 am -
2 stops8h 30m
Sun 11/299:40 am -
1 stop6h 35m
Deal found 9/21![Southwest logo]()
$499
Last-minute flights from Orlando to ChesapeakeDiscover last-minute flight deals from Orlando to Chesapeake. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Chesapeake. Data last updated September 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/212:57 pm -
Nonstop2h 07m
Tue 10/68:05 am -
Nonstop2h 16m
Deal found 9/17![Breeze Airways logo]()
$132
This Priceline deal was found by Cheapflights users on 9/20. 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 10/611:06 am -
Nonstop2h 07m
Tue 10/67:43 pm -
Nonstop2h 12m
Deal found 9/20![Multiple Airlines logo]()
$120
This Super.com deal was found by Cheapflights users on 9/19. 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 10/64:44 pm -
Nonstop2h 04m
Sun 10/187:41 pm -
Nonstop2h 13m
Deal found 9/19![Frontier logo]()
$126
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/74:44 pm -
Nonstop2h 04m
Sun 10/117:41 pm -
Nonstop2h 13m
Deal found 9/17![Frontier logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:56 am -
1 stop6h 48m
Sun 10/117:41 pm -
Nonstop2h 13m
Deal found 9/17![Frontier logo]()
$135
This Priceline deal was found by Cheapflights users on 9/17. 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.
Sat 10/1010:56 am -
Nonstop2h 07m
Sat 10/173:50 pm -
1 stop5h 40m
Deal found 9/17![Multiple Airlines logo]()
$124
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:44 pm -
Nonstop2h 02m
Sun 10/117:41 pm -
Nonstop2h 13m
Deal found 9/18![Frontier logo]()
$136
This Super.com deal was found by Cheapflights users on 9/21. 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 10/144:44 pm -
Nonstop2h 02m
Tue 10/207:41 pm -
Nonstop2h 13m
Deal found 9/21![Frontier logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/154:44 pm -
Nonstop2h 02m
Tue 10/201:19 pm -
1 stop8h 11m
Deal found 9/20![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/2410:56 am -
Nonstop2h 07m
Sun 10/256:00 am -
Nonstop2h 16m
Deal found 9/19![Breeze Airways logo]()
$137
This CheapOair deal was found by Cheapflights users on 9/18. 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 10/296:07 am -
1 stop6h 39m
Tue 11/37:41 pm -
Nonstop2h 15m
Deal found 9/18![Frontier logo]()
$127
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 September 22, 2026.
Search for one-way flight options from Orlando to Chesapeake. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Super.com deal was found by Cheapflights users on 9/21. 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 10/207:10 am -
1 stop5h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$53
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/2110:56 am -
Nonstop2h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Breeze Airways logo]()
$58
This Orbitz deal was found by Cheapflights users on 9/17. 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.
Wed 12/167:15 am -
1 stop11h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$59
This deal was found by Cheapflights users on 9/18. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:30 am -
1 stop5h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$60
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/1410:56 am -
Nonstop2h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Breeze Airways logo]()
$61
This Super.com deal was found by Cheapflights users on 9/17. 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 11/174:44 pm -
Nonstop2h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/149:25 am -
1 stop27h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/242:52 pm -
1 stop21h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/2410:56 am -
Nonstop2h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Breeze Airways logo]()
$68
This Priceline deal was found by Cheapflights users on 9/18. 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.
Sat 10/174:44 pm -
Nonstop2h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 11/189:25 am -
1 stop27h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$70
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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $120 (Priceline) |
One-way from | $53 (Super.com) |
Popular in | July |
Cheapest in | April |
Average price | $198 |
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 7,457,451 searches. Data last updated September 22, 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 Orlando - ORF Norfolk
MCOORF
Orlando
Tue 11/10
4:44 pm-6:44 pm
Nonstop2h 00m
Norfolk
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$73
OrlandoNorfolk
MCO Orlando - ORF Norfolk
MCOORF
Orlando
Wed 12/16
8:50 am-5:25 pm
2 stops8h 35m
Norfolk
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
OrlandoNorfolk
MCO Orlando - ORF Norfolk
MCOORF
Orlando
Thu 12/17
9:45 am-4:18 pm
1 stop6h 33m
Norfolk
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$124
OrlandoNorfolk
MCO Orlando - ORF Norfolk
MCOORF
Orlando
Tue 12/15
7:45 pm-12:06 am
1 stop4h 21m
Norfolk
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$124
OrlandoNorfolk
MCO Orlando - ORF Norfolk
MCOORF
Orlando
Mon 10/12
10:35 pm-9:20 am
1 stop10h 45m
Norfolk
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
OrlandoNorfolk
MCO Orlando - ORF Norfolk
MCOORF
Orlando
Tue 11/10
1:45 pm-9:15 pm
2 stops7h 30m
Norfolk
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
OrlandoNorfolk
MCO Orlando - ORF Norfolk
MCOORF
Orlando
Mon 11/16
7:45 pm-12:48 am
1 stop5h 03m
Norfolk
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
OrlandoNorfolk
MCO Orlando - ORF Norfolk
MCOORF
Orlando
Tue 10/20
11:06 am-1:13 pm
Nonstop2h 07m
Norfolk
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$147
OrlandoNorfolk
MCO Orlando - ORF Norfolk
MCOORF
Orlando
Wed 10/14
4:53 pm-12:38 pm
1 stop19h 45m
Norfolk
Tue 10/20
1:19 pm-9:30 pm
1 stop8h 11m
$157
OrlandoNorfolk
MCO Orlando - ORF Norfolk
MCOORF
Orlando
Thu 11/19
1:45 pm-9:15 pm
2 stops7h 30m
Norfolk
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
Showing 1-10 of 23 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 September 22, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 31% on flights from Orlando to Chesapeake by exploring options for tickets in the morning.
Weekly flight availability from Orlando to Chesapeake
Explore weekly flight availability from Orlando to Chesapeake. 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 September 22, 2026.
The most flights from ORL to C6E are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Orlando to Chesapeake?
Airfare is below average for this route at the moment.
Orlando to Chesapeake flights typically cost between $129 and $242 in October.The cheapest round-trip price found within the last 5 days was $120 on Multiple Airlines (Oct 6-Oct 6).
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 September 19, 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 September 22, 2026.
Get a feel of what it's like to fly with Breeze Airways,Southwest, andAmerican Airlines 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.
Crew
8.8
Boarding
8.4
Overall
8.2
Comfort
8.2
Entertainment
6.7
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Boarding
8.4
Overall
8.2
Comfort
8.2
Entertainment
6.7
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Boarding
8.4
Overall
8.2
Comfort
8.2
Entertainment
6.7
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Boarding
8.4
Overall
8.2
Comfort
8.2
Entertainment
6.7
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Crew
8.8
Boarding
8.4
Overall
8.2
Comfort
8.2
Entertainment
6.7
Food
6.8
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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Orlando and Chesapeake flights
Browse other Orlando and Chesapeake flight options. Last updated on September 22, 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 7,457,451 searches. Data last updated September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$147 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$304 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$86 | Average$136 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$97 | Average$227 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$113 | Average$196 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$135 | Average$246 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$191 | Average$359 | FlexibilityNo cancel fee | On-time71% |