HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$48+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — RIC
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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.

The best prices from Orlando to Chesapeake are usually found in March or April, booked 43 days in advance, depart on a Thursday or Tuesday and return on a Tuesday

Cheap flight deals from Orlando to Chesapeake

Keep the following information in mind while searching for Orlando to Chesapeake flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$83
(Cheapflightsfares)

One-way from

$48
(Cheapflightsfares)

Popular in

January

Cheapest in

March

Average price

$152
Provider with most accurate pricing for Orlando (ORL)-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Norfolk flights.
Search Deals
From Orlando (ORL) to Chesapeake
Search Deals
One-way flight from Orlando (ORL) to Chesapeake
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

Find flight deals from Orlando to Chesapeake

Cheapest flights from Orlando to Chesapeake
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 February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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.
Tue 3/185:25 amMCO - ORF
1 stop5h 05mSpirit Airlines
Wed 3/197:41 pmORF - MCO
Nonstop2h 15mSpirit Airlines
Deal found 2/20$83
This Justfly.com deal was found by Cheapflights users on 2/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/209:49 amMCO - ORF
Nonstop1h 58mMultiple Airlines
Sun 3/237:11 pmORF - MCO
Nonstop2h 19mMultiple Airlines
Deal found 2/20$86
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 4/248:25 amMCO - ORF
Nonstop2h 07mFrontier
Thu 5/111:21 amORF - MCO
Nonstop2h 07mFrontier
Deal found 2/20$106
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/267:00 amMCO - ORF
1 stop25h 45mBreeze Airways
Fri 2/289:14 pmORF - MCO
1 stop20h 38mBreeze Airways
Deal found 2/19$183
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/1910:05 amMCO - ORF
2 stops7h 05mSouthwest
Sun 3/236:10 pmORF - MCO
1 stop6h 25mSouthwest
Deal found 2/19$366
This United deal was found by Cheapflights users on 2/20. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/267:20 amMCO - ORF
1 stop7h 06mUnited Airlines
Sat 5/36:00 amORF - MCO
2 stops9h 28mUnited Airlines
Deal found 2/20$377
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/196:15 amMCO - ORF
1 stop6h 38mDelta
Mon 6/236:05 pmORF - MCO
1 stop6h 37mDelta
Deal found 2/20$383

Find flights from Orlando to Chesapeake within your budget

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 February 20, 2025.

Fly from

Orlando

Fly to

Chesapeake

Route

Depart

Return

Price

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Tue 3/18

5:25 am-10:30 am

1 stop5h 05m

Norfolk

Wed 3/19

7:41 pm-9:56 pm

Nonstop2h 15m

$83

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 3/20

9:49 am-11:47 am

Nonstop1h 58m

Norfolk

Sun 3/23

7:11 pm-9:30 pm

Nonstop2h 19m

$86

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 3/7

6:30 pm-11:59 pm

1 stop5h 29m

Norfolk

Sun 3/9

6:00 am-2:02 pm

1 stop8h 02m

$277

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Mon 5/12

8:00 am-6:45 pm

2 stops10h 45m

Norfolk

Thu 5/15

4:30 pm-9:30 pm

1 stop5h 00m

$350

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Sat 4/26

7:20 am-2:26 pm

1 stop7h 06m

Norfolk

Sat 5/3

6:00 am-3:28 pm

2 stops9h 28m

$377

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 3/7

5:27 pm-10:51 pm

1 stop5h 24m

Norfolk

Sun 3/9

6:42 pm-11:12 pm

1 stop4h 30m

$405

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Thu 4/24

6:10 pm-8:34 am

2 stops14h 24m

Norfolk

Thu 5/1

8:36 pm-6:07 pm

2 stops21h 31m

$949

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Sun 5/18

8:25 am-10:31 am

Nonstop2h 06m

$48

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Fri 3/21

4:43 pm-6:46 pm

Nonstop2h 03m

$52

OrlandoNorfolk

MCO - ORF

MCOORF

Orlando

Sat 5/17

8:45 am-9:30 am

1 stop24h 45m

$73

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 15 results
1
2

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.
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.

Travel insights for flights from Orlando to Chesapeake

Get recent, data-driven insights about flights from Orlando to Chesapeake including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Orlando to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Orlando to Chesapeake. Price data was last updated on February 14, 2025.

To ensure you get the cheapest price possible for a flight from Orlando to Chesapeake, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Orlando to Chesapeake?

Currently, January is the cheapest month in which you can book a flight from Orlando to Chesapeake (average of $281). Flying from Orlando to Chesapeake in June is currently the most expensive (average of $372). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 February 20, 2025.

When flying from Orlando to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 February 16, 2025.

Travelers seeking maximum savings on their Orlando to Chesapeake flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chesapeake ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Chesapeake when rainfall is around 2.9 in.

Temperature in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chesapeake, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

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 February 20, 2025.
Read through reviews of airlines operating flights from Orlando to Chesapeake, such as Southwest, Breeze Airways and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Breeze Airways
8.1
Very good
150 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

  • What are the cheapest airlines to fly from Orlando to Chesapeake one-way?

    $48 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and Breeze Airways, with prices starting from $49 and $73, respectively.

  • What are the most reliable airlines from Orlando to Chesapeake?

    The top 3 most reliable airlines when flying from Orlando to Chesapeake are Spirit Airlines (91%), Azul (81%) and JetBlue (81%).

  • What are the cheapest flights from Orlando to Chesapeake?

    While on average a flight from Orlando to Chesapeake is generally $169, our data shows the cheapest flight currently is $50. When looking at the most popular route, (Orlando - Norfolk), you can expect to pay $62 for that flight.

  • Can I find deals for flights from Orlando to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Orlando to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Orlando to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Orlando to Chesapeake.

  • Can I find deals for business class flights from Orlando to Chesapeake?

    Yes. Cheapflights offers flight deals from Orlando to Chesapeake by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Orlando to Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from Orlando to Chesapeake (average of $281). Flying from Orlando to Chesapeake in June is currently the most expensive (average of $372). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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 for Orlando to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to Dulles Intl flights
Tampa to Dulles Intl flights
Orlando to Reagan-National flights
Miami to Reagan-National flights
Tampa to Reagan-National flights
Fort Lauderdale to Dulles Intl flights
Miami to Dulles Intl flights
Fort Lauderdale to Reagan-National flights
Jacksonville to Dulles Intl flights
Jacksonville to Reagan-National flights
West Palm Beach to Dulles Intl flights
Orlando to Raleigh flights
Fort Myers to Dulles Intl flights
Tampa to Raleigh flights
Fort Lauderdale to Raleigh flights
West Palm Beach to Reagan-National flights
Miami to Raleigh flights
Orlando to Richmond flights
Fort Myers to Reagan-National flights
Sarasota to Reagan-National flights
Fort Lauderdale to Richmond flights
Fort Lauderdale to Norfolk flights
Miami to Richmond flights
Tampa to Richmond flights
Pensacola to Reagan-National flights
Pensacola to Dulles Intl flights
Orlando to Norfolk flights
Miami to Norfolk flights
Panama City to Reagan-National flights
Pensacola to Raleigh flights
Tampa to Norfolk flights
Tallahassee to Reagan-National flights
Panama City to Dulles Intl flights
Gainesville to Dulles Intl flights
Jacksonville to Richmond flights
Fort Myers to Raleigh flights
Tallahassee to Dulles Intl flights
Sarasota to Dulles Intl flights
Sarasota to Raleigh flights
Jacksonville to Raleigh flights
Orlando to Greensboro flights
Gainesville to Reagan-National flights
Jacksonville to Norfolk flights
Valparaiso to Dulles Intl flights
Tampa to Greensboro flights
Orlando to Roanoke flights
Fort Lauderdale to Greensboro flights
West Palm Beach to Raleigh flights
Tampa to Roanoke flights
Pensacola to Richmond flights

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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$115FlexibilityNo cancel feeOn-time65%
FrontierCheapest$59Average$119FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$74Average$121FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$90Average$222FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$305FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$266FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$202Average$311FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.