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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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORL
Apr 6 — Apr 131
Mon 4/6
Mon 4/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in May or July, booked 90 days in advance, depart on a Sunday or Monday and return on a Thursday

Cheap 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 March 7, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/163:26 pm
ORF
-
MCO
Nonstop2h 15m
Frontier
Fri 3/205:45 am
MCO
-
ORF
Nonstop2h 00m
Frontier
Deal found 3/3$79
This Trip.com deal was found by Cheapflights users on 3/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/233:26 pm
ORF
-
MCO
Nonstop2h 15m
Frontier
Thu 3/263:44 pm
MCO
-
ORF
Nonstop2h 04m
Frontier
Deal found 3/6$81
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:43 pm
ORF
-
MCO
Nonstop2h 12m
Frontier
Thu 5/2112:09 pm
MCO
-
ORF
Nonstop2h 11m
Frontier
Deal found 3/3$83
This Mytrip deal was found by Cheapflights users on 3/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/166:45 am
ORF
-
MCO
Nonstop2h 06m
Multiple Airlines
Fri 3/205:45 am
MCO
-
ORF
Nonstop2h 00m
Multiple Airlines
Deal found 3/3$84
This Super.com deal was found by Cheapflights users on 3/4. 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.
Sun 3/156:45 am
ORF
-
MCO
Nonstop2h 06m
Spirit Airlines
Sat 3/217:50 pm
MCO
-
ORF
Nonstop1h 57m
Spirit Airlines
Deal found 3/4$87
This Mytrip deal was found by Cheapflights users on 3/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/217:25 am
ORF
-
MCO
Nonstop2h 10m
Breeze Airways
Wed 3/251:51 pm
MCO
-
ORF
Nonstop2h 00m
Breeze Airways
Deal found 3/3$88
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/163:26 pm
ORF
-
MCO
Nonstop2h 15m
Frontier
Sat 3/2112:24 pm
MCO
-
ORF
Nonstop2h 07m
Frontier
Deal found 3/2$89
This Super.com deal was found by Cheapflights users on 3/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:16 pm
ORF
-
MCO
Nonstop2h 11m
Frontier
Sun 5/3112:09 pm
MCO
-
ORF
Nonstop2h 11m
Frontier
Deal found 3/3$90
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/213:26 pm
ORF
-
MCO
Nonstop2h 15m
Multiple Airlines
Wed 3/257:50 pm
MCO
-
ORF
Nonstop1h 57m
Multiple Airlines
Deal found 3/2$91
This Super.com deal was found by Cheapflights users on 3/4. 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 3/213:26 pm
ORF
-
MCO
Nonstop2h 15m
Frontier
Sat 3/2812:24 pm
MCO
-
ORF
Nonstop2h 07m
Frontier
Deal found 3/4$92
This Mytrip deal was found by Cheapflights users on 3/5. 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.
Sat 3/217:25 am
ORF
-
MCO
Nonstop2h 10m
Breeze Airways
Sat 3/2810:15 am
MCO
-
ORF
Nonstop2h 00m
Breeze Airways
Deal found 3/5$94
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 3/1810:31 pm
ORF
-
SFB
1 stop25h 08m
Multiple Airlines
Mon 3/307:00 pm
SFB
-
ORF
2 stops24h 46m
Multiple Airlines
Deal found 3/4$351

Find flight deals from Chesapeake to Orlando

Keep the following information in mind while searching for Chesapeake to Orlando flight deals. Data was last updated March 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$79
(Kiwi.com)

One-way from

$43
(Super.com)

Popular in

November

Cheapest in

May

Average price

$152
Provider with most accurate pricing for Norfolk-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Orlando (ORL) flights.
Search Deals
From Chesapeake to Orlando (ORL)
Search Deals
One-way flight from Chesapeake to Orlando (ORL)
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 7, 2026.
Use the filters below to find and compare flights from Chesapeake to Orlando that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 3/18

7:05 am-9:15 am

Nonstop2h 10m

Orlando

Mon 3/23

3:06 pm-5:06 pm

Nonstop2h 00m

$183

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 5/6

3:02 pm-10:40 pm

1 stop7h 38m

Orlando

Tue 5/12

6:15 am-12:58 pm

1 stop6h 43m

$233

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 4/8

12:45 pm-5:20 pm

1 stop4h 35m

Orlando

Tue 4/14

6:50 pm-8:50 pm

Nonstop2h 00m

$233

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 4/14

6:50 am-3:00 pm

2 stops8h 10m

Orlando

Mon 4/20

6:05 pm-10:55 pm

1 stop4h 50m

$238

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 9/3

7:00 am-9:16 am

Nonstop2h 16m

Orlando

Sat 9/12

11:40 am-6:46 pm

1 stop7h 06m

$239

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 6/26

5:24 pm-7:40 pm

Nonstop2h 16m

Orlando

Sun 7/5

9:56 am-12:14 pm

Nonstop2h 18m

$258

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 4/30

7:25 pm-1:18 am

1 stop5h 53m

Orlando

Tue 5/5

6:45 pm-12:37 am

1 stop5h 52m

$269

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 5/4

6:15 am-12:19 pm

1 stop6h 04m

Orlando

Wed 5/6

7:15 am-2:24 pm

1 stop7h 09m

$300

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 4/17

6:05 am-1:55 pm

2 stops7h 50m

Orlando

Sat 4/25

8:15 am-3:25 pm

2 stops7h 10m

$302

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 7/21

6:05 am-2:40 pm

2 stops8h 35m

Orlando

Wed 7/29

3:10 pm-10:35 pm

2 stops7h 25m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/6

Showing 1-10 of 38 resultsSorted by cheapest first
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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 February 27, 2026.

To ensure you get the cheapest price possible for a flight from Chesapeake to Orlando, you should look to book at least 90 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, September is the cheapest month in which you can book a flight from Chesapeake to Orlando (average of $42). Flying from Chesapeake to Orlando in December is currently the most expensive (average of $84). 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 March 7, 2026.

It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 37% on the flight price compared to flying at noon, which is usually more expensive.

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 21, 2026.

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

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 March 7, 2026.
Peruse reviews from past customers who have flown with Breeze Airways, Southwest, 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.
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Boarding

8.3

Comfort

8.2

Overall

8.1

Food

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.1
Very good
271 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Boarding

8.3

Comfort

8.2

Overall

8.1

Food

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Southwest
8.0
Very good
4,311 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Boarding

8.3

Comfort

8.2

Overall

8.1

Food

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.1
Good
11,398 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Boarding

8.3

Comfort

8.2

Overall

8.1

Food

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Spirit Airlines
6.3
Okay
8,498 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Boarding

8.3

Comfort

8.2

Overall

8.1

Food

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Frontier
5.7
Fair
3,041 reviews
Breeze Airways
8.1
Very good
271 reviews

Entertainment

6.6

Crew

8.7

Boarding

8.3

Comfort

8.2

Overall

8.1

Food

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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 10m. Fly via Breeze Airways, Delta, or United Airlines 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 cheapest airlines to fly from Chesapeake to Orlando one-way?

    One-way options have recently been found by users for as low as $36 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $40 and Allegiant Air from $52 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 (76%), Southwest (67%) and JetBlue (66%).

  • What are the cheapest flights from Chesapeake to Orlando?

    The cheapest flight price from Chesapeake to Orlando is $43. On average you can expect to pay $273. The most popular route, (Norfolk - Orlando), can usually be booked for $78.

  • 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, September is the cheapest month in which you can book a flight from Chesapeake to Orlando (average of $42). Flying from Chesapeake to Orlando in December is currently the most expensive (average of $84). 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 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 March 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$41Average$127FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$142FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$81Average$165FlexibilityNo cancel feeOn-time88%
DeltaCheapest$88Average$312FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$90Average$217FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$99Average$293FlexibilityNo cancel feeOn-time63%
Breeze AirwaysCheapest$100Average$245FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$138Average$476FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$162Average$333FlexibilityNo cancel feeOn-time71%

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