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$50+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in May or March, booked 40 days in advance, depart on a Monday or Tuesday 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 July 3, 2025.

Round-trip from

$99
(Priceline)

One-way from

$50
(FlightHub)

Popular in

October

Cheapest in

May

Average price

$182
From Chesapeake to Orlando (ORL)
Search Deals
One-way flight from Chesapeake to Orlando (ORL)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This FlightHub deal was found by Cheapflights users on 7/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/75:38 pmORF - MCO
Nonstop2h 10mSpirit Airlines
Sat 9/132:39 pmMCO - ORF
Nonstop2h 04mSpirit Airlines
Deal found 7/3$99
This Frontier deal was found by Cheapflights users on 7/2. 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 9/74:57 pmORF - MCO
Nonstop2h 09mFrontier
Sun 9/142:05 pmMCO - ORF
Nonstop2h 07mFrontier
Deal found 7/2$100
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Tue 7/295:50 amORF - MCO
Nonstop2h 05mMultiple Airlines
Thu 8/74:43 pmMCO - ORF
Nonstop2h 11mMultiple Airlines
Deal found 7/1$101
This Booking.com deal was found by Cheapflights users on 7/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/13:15 pmORF - SFB
Nonstop1h 55mAllegiant Air
Mon 8/47:40 amSFB - ORF
Nonstop1h 50mAllegiant Air
Deal found 7/1$109
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/83:15 pmORF - SFB
Nonstop1h 55mMultiple Airlines
Mon 8/117:41 pmSFB - ORF
2 stops20h 44mMultiple Airlines
Deal found 7/2$199

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 July 3, 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

Sun 9/7

4:57 pm-7:06 pm

Nonstop2h 09m

Orlando

Sat 9/13

2:39 pm-4:43 pm

Nonstop2h 04m

$99

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 9/7

4:57 pm-7:06 pm

Nonstop2h 09m

Orlando

Sun 9/14

2:05 pm-4:12 pm

Nonstop2h 07m

$100

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 9/19

5:38 pm-7:48 pm

Nonstop2h 10m

Orlando

Sun 9/21

2:39 pm-4:43 pm

Nonstop2h 04m

$102

NorfolkOrlando

ORF - SFB

ORFSFB

Norfolk

Fri 8/1

3:15 pm-5:10 pm

Nonstop1h 55m

Orlando Sanford Intl

Mon 8/4

7:40 am-9:30 am

Nonstop1h 50m

$109

NorfolkOrlando

ORF - SFB

ORFSFB

Norfolk

Fri 8/8

3:15 pm-5:10 pm

Nonstop1h 55m

Orlando Sanford Intl

Mon 8/11

7:41 pm-4:25 pm

2 stops20h 44m

$199

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 8/24

5:34 pm-7:42 pm

Nonstop2h 08m

$50

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 8/3

2:03 pm-4:15 pm

Nonstop2h 12m

$65

NorfolkOrlando

ORF - SFB

ORFSFB

Norfolk

Mon 7/14

3:20 pm-5:15 pm

Nonstop1h 55m

$68

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 9/9

6:15 am-11:57 am

1 stop5h 42m

$79

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 10/14

7:24 pm-11:29 pm

1 stop4h 05m

$83

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 15 results
1
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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 June 27, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake to Orlando, you should look to book at least 40 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 July 3, 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 June 29, 2025.

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

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 July 3, 2025.

The most flights from C6E to ORL are scheduled on a Thursday (6 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (3 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 July 3, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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
4,266 reviews

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,916 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $50 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $65 and Allegiant Air from $68 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 Azul (74%), JetBlue (73%) and Spirit Airlines (70%).

  • What are the cheapest flights from Chesapeake to Orlando?

    The cheapest flight price from Chesapeake to Orlando is $48. On average you can expect to pay $171. The most popular route, (Norfolk - Orlando), can usually be booked for $91.

  • 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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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$43Average$167FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$81Average$133FlexibilityNo cancel feeOn-time88%
FrontierCheapest$82Average$179FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$127Average$256FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$147Average$332FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$167Average$320FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$348FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$195Average$375FlexibilityNo cancel feeOn-time69%

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