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$42+ Cheap flights from Chesapeake, VA to Orlando (ORL)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
1 adult, Economy
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The best prices from Chesapeake to Orlando are usually found in February or March, booked 64 days in advance, depart on a Tuesday or Monday and return on a Thursday

Cheap flight deals from Chesapeake to Orlando

Keep the following information in mind while searching for Chesapeake to Orlando flight deals. Data was last updated February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(FlightHub)

One-way from

$42
(FlightHub)

Popular in

October

Cheapest in

February

Average price

$194
Provider with most accurate pricing for Norfolk-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Orlando (ORL) flights.
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From Chesapeake to Orlando (ORL)
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One-way flight from Chesapeake to Orlando (ORL)
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Highest demand for flights based on searches. 8% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Chesapeake to Orlando

Cheapest flights from Chesapeake to Orlando
Explore the most affordable flight options available from Chesapeake to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/267:44 pmORF - MCO
Nonstop2h 06mMultiple Airlines
Sun 6/17:00 amMCO - ORF
Nonstop2h 13mMultiple Airlines
Deal found 2/23$93
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/277:44 pmORF - MCO
Nonstop2h 06mSpirit Airlines
Sun 6/112:39 pmMCO - ORF
Nonstop2h 00mSpirit Airlines
Deal found 2/23$94
This Cheapflightsfares deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/63:19 pmORF - SFB
Nonstop1h 52mAllegiant Air
Mon 6/97:45 amSFB - ORF
Nonstop1h 53mAllegiant Air
Deal found 2/22$97
This Cheapflightsfares deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/26:12 pmORF - MCO
Nonstop2h 18mFrontier
Tue 3/43:28 pmMCO - ORF
Nonstop2h 06mFrontier
Deal found 2/22$121
This Mytrip deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/24:05 pmORF - MCO
1 stop23h 30mBreeze Airways
Wed 3/57:45 pmMCO - ORF
1 stop13h 45mBreeze Airways
Deal found 2/23$144
This Mytrip deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/277:23 pmORF - SFB
2 stops28h 16mMultiple Airlines
Mon 3/3112:34 pmSFB - ORF
Nonstop1h 49mMultiple Airlines
Deal found 2/22$250

Find flights from Chesapeake to Orlando within your budget

Customize your flight search to find flights from Chesapeake to Orlando that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 23, 2025.

Fly from

Chesapeake

Fly to

Orlando

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 5/26

7:44 pm-9:50 pm

Nonstop2h 06m

Orlando

Sun 6/1

7:00 am-9:13 am

Nonstop2h 13m

$93

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 5/27

7:44 pm-9:50 pm

Nonstop2h 06m

Orlando

Sun 6/1

12:39 pm-2:39 pm

Nonstop2h 00m

$94

NorfolkOrlando

ORF - SFB

ORFSFB

Norfolk

Fri 6/6

3:19 pm-5:11 pm

Nonstop1h 52m

Orlando Sanford Intl

Mon 6/9

7:45 am-9:38 am

Nonstop1h 53m

$97

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 3/23

7:11 pm-9:30 pm

Nonstop2h 19m

Orlando

Sun 3/30

3:37 pm-5:43 pm

Nonstop2h 06m

$126

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 3/7

9:14 pm-5:52 pm

1 stop20h 38m

Orlando

Sat 3/29

7:45 pm-9:30 am

1 stop13h 45m

$188

NorfolkOrlando

ORF - SFB

ORFSFB

Norfolk

Fri 3/14

8:44 am-10:45 am

Nonstop2h 01m

Orlando Sanford Intl

Sat 3/22

9:49 pm-6:28 pm

2 stops20h 39m

$244

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 3/11

4:35 pm-6:50 pm

Nonstop2h 15m

Orlando

Thu 3/13

9:35 am-11:30 am

Nonstop1h 55m

$313

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 4/8

11:22 am-5:14 pm

1 stop5h 52m

Orlando

Sun 4/13

5:25 pm-10:38 pm

1 stop5h 13m

$322

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 3/8

4:40 pm-11:36 pm

1 stop6h 56m

Orlando

Mon 3/17

7:45 pm-12:03 am

1 stop4h 18m

$333

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 4/14

12:17 pm-2:27 pm

Nonstop2h 10m

$42

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 19 results
1
2

Best time to book a flight from Chesapeake to Orlando

Have a flexible travel schedule? Discover the best time to fly to Orlando from Chesapeake with our price prediction graph.
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 Chesapeake to Orlando

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

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

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

To ensure you get the cheapest price possible for a flight from Chesapeake to Orlando, you should look to book at least 64 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 Chesapeake to Orlando?

Currently, May is the cheapest month in which you can book a flight from Chesapeake to Orlando (average of $206). Flying from Chesapeake to Orlando in November is currently the most expensive (average of $289). 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 C6E to ORL?

Find hourly flight availability from Chesapeake to Orlando. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 23, 2025.

When flying from Chesapeake to Orlando, 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 Chesapeake to Orlando?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Orlando. Price data was last updated on February 16, 2025.

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

Rainfall in Orlando by month

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

In terms of precipitation, rainfall in Orlando ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Orlando when rainfall is around 2.4 in.

Temperature in Orlando by month

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

If weather is an important factor for your trip to Orlando, 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 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

Reviews of airlines servicing Orlando

Get insights into the airlines that provide service to Orlando. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Orlando. Reviews last updated February 23, 2025.
Read reviews from past customers who have flown Southwest, Breeze Airways and Delta from Chesapeake to Orlando. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Southwest
8.1
Very good
4,387 reviews
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Breeze Airways
8.1
Very good
150 reviews
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Delta
8.0
Very good
8,191 reviews
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

United Airlines
7.4
Good
8,746 reviews
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Allegiant Air
7.3
Good
762 reviews
Southwest
8.1
Very good
4,387 reviews

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Orlando. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    One-way options have recently been found by users for as low as $42 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $47 and Allegiant Air from $49 one-way.

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

    The top 3 most reliable airlines when flying from Chesapeake to Orlando are Spirit Airlines (82%), Azul (74%) and JetBlue (74%).

  • What are the cheapest flights from Chesapeake to Orlando?

    The cheapest flight price from Chesapeake to Orlando is $57. On average you can expect to pay $195. The most popular route, (Norfolk - Orlando), can usually be booked for $62.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chesapeake to Orlando 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 Chesapeake to Orlando?

    Currently, May is the cheapest month in which you can book a flight from Chesapeake to Orlando (average of $206). Flying from Chesapeake to Orlando in November is currently the most expensive (average of $289). 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

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Chesapeake to Orlando

Discover the top 9 airlines that operate flights from Chesapeake to Orlando. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$142FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$45Average$135FlexibilityNo cancel feeOn-time88%
FrontierCheapest$78Average$170FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$118Average$258FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$133Average$355FlexibilityNo cancel feeOn-time69%
Breeze AirwaysCheapest$149Average$179FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$326FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$367FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$217Average$373FlexibilityNo cancel feeOn-time63%
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