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$43+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in May or March, booked 71 days in advance, depart on a Monday or Thursday 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 September 16, 2025.

Round-trip from

$85
(Kiwi.com)

One-way from

$43
(Cheapflightsfares)

Popular in

October

Cheapest in

May

Average price

$200
From Chesapeake to Orlando (ORL)
Search Deals
One-way flight from Chesapeake to Orlando (ORL)
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/175:38 pmORF - MCO
Nonstop2h 09mMultiple Airlines
Sun 10/197:00 amMCO - ORF
Nonstop2h 02mMultiple Airlines
Deal found 9/14$85
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 10/129:47 amORF - MCO
Nonstop2h 08mFrontier
Sun 10/197:00 amMCO - ORF
Nonstop2h 02mFrontier
Deal found 9/16$88
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 9/145:47 pmORF - MCO
Nonstop2h 11mFrontier
Sun 9/212:50 pmMCO - ORF
Nonstop2h 07mFrontier
Deal found 9/14$91
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/199:47 amORF - MCO
Nonstop2h 08mFrontier
Thu 10/237:00 amMCO - ORF
Nonstop2h 02mFrontier
Deal found 9/15$92
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/255:12 pmORF - MCO
Nonstop2h 11mFrontier
Sun 9/282:50 pmMCO - ORF
Nonstop2h 07mFrontier
Deal found 9/14$97
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 11/88:01 amORF - MCO
Nonstop2h 08mSpirit Airlines
Sat 11/1510:00 pmMCO - ORF
Nonstop2h 07mSpirit Airlines
Deal found 9/14$99
This Priceline deal was found by Cheapflights users on 9/16. 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 10/305:38 pmORF - MCO
Nonstop2h 09mSpirit Airlines
Mon 11/32:39 pmMCO - ORF
Nonstop2h 00mSpirit Airlines
Deal found 9/16$100
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 9/215:47 pmORF - MCO
Nonstop2h 11mFrontier
Thu 9/256:00 amMCO - ORF
1 stop5h 24mFrontier
Deal found 9/15$109
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:27 pmORF - SFB
1 stop17h 39mMultiple Airlines
Thu 11/206:11 pmSFB - ORF
2 stops23h 25mMultiple Airlines
Deal found 9/14$315
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/19:39 pmORF - SFB
1 stop13h 51mMultiple Airlines
Sun 10/51:31 pmSFB - ORF
2 stops32h 47mMultiple Airlines
Deal found 9/16$317
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/229:39 pmORF - SFB
1 stop13h 51mMultiple Airlines
Tue 10/285:13 pmSFB - ORF
2 stops29h 33mMultiple Airlines
Deal found 9/15$380
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/159:39 pmORF - SFB
1 stop13h 51mMultiple Airlines
Wed 10/221:18 pmSFB - ORF
2 stops9h 28mMultiple Airlines
Deal found 9/15$445

Cheapflights Fare Finder

 
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 September 16, 2025.
Use the filters below to find and compare flights from Chesapeake to Orlando that are best for you.

Fly from

Chesapeake

Fly to

Orlando

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 10/3

4:57 pm-7:12 pm

Nonstop2h 15m

Orlando

Fri 10/10

7:52 pm-10:02 pm

Nonstop2h 10m

$113

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 12/10

6:10 am-10:55 am

1 stop4h 45m

Orlando

Wed 12/17

11:22 am-4:47 pm

1 stop5h 25m

$135

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 11/15

5:17 pm-11:30 pm

1 stop6h 13m

Orlando

Sat 11/22

1:58 pm-9:38 pm

1 stop7h 40m

$170

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 11/15

4:10 pm-9:30 pm

1 stop5h 20m

Orlando

Mon 11/24

6:35 pm-11:35 pm

1 stop5h 00m

$175

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 11/1

3:05 pm-9:39 pm

1 stop6h 34m

Orlando

Sat 11/8

6:00 am-11:29 am

1 stop5h 29m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 3/3

12:30 pm-7:40 pm

1 stop7h 10m

Orlando

Wed 3/4

5:15 pm-10:55 pm

1 stop5h 40m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 10/18

4:23 pm-9:51 pm

1 stop5h 28m

Orlando

Wed 10/22

6:00 am-11:29 am

1 stop5h 29m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 10/20

7:45 pm-11:59 pm

1 stop4h 14m

Orlando

Wed 10/22

5:30 pm-9:33 pm

1 stop4h 03m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 1/11

3:05 pm-7:40 pm

1 stop4h 35m

Orlando

Fri 1/16

5:15 pm-10:55 pm

1 stop5h 40m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 10/31

2:45 pm-8:20 pm

1 stop5h 35m

Orlando

Tue 11/4

3:30 pm-10:00 pm

2 stops6h 30m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 33 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Orlando

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 September 12, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake to Orlando, you should look to book at least 71 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 September 16, 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 September 14, 2025.

Travelers seeking maximum savings on their Chesapeake to Orlando flight should consider departing on Monday afternoons 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.

Weekly flight availability from Chesapeake to Orlando

Explore weekly flight availability from Chesapeake to Orlando. 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 16, 2025.

The most flights from C6E to ORL are scheduled on a Monday (4 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Chesapeake to Orlando?

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 September 16, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and American Airlines from Chesapeake to Orlando to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chesapeake to Orlando?

    There are many flights that can get you from Chesapeake to Orlando in 2h 15m. Fly via Breeze Airways, United Airlines, or Southwest to get the fastest option. There are 655 mi between Chesapeake and Orlando. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The top 3 most reliable airlines when flying from Chesapeake to Orlando are Southwest (74%), Azul (67%) and JetBlue (66%).

  • What are the cheapest flights from Chesapeake to Orlando?

    The cheapest flight price from Chesapeake to Orlando is $37. On average you can expect to pay $149. The most popular route, (Norfolk - Orlando), can usually be booked for $85.

  • 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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Alternative routes for Chesapeake to Orlando

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Chesapeake to Orlando

Discover the top 8 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$167FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$159FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$81Average$129FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$111Average$316FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$117Average$269FlexibilityNo cancel feeOn-time62%
DeltaCheapest$134Average$346FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$167Average$325FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$205Average$374FlexibilityNo cancel feeOn-time69%

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