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 $40 on Frontier. Other airlines that offer cheap prices include Breeze Airways from $59 and Southwest from $88 one-way.

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.

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).

What are the cheapest flights from Chesapeake to Orlando?

The cheapest flight price from Chesapeake to Orlando is $64. On average you can expect to pay $225. The most popular route, (Norfolk - Orlando), can usually be booked for $122.

What are the most reliable airlines from Chesapeake to Orlando?

The top 3 most reliable airlines when flying from Chesapeake to Orlando are Azul (87%), JetBlue (83%) and Southwest (81%).

What are the most popular airlines that fly from Chesapeake to Orlando?

Consider Frontier, Breeze Airways or Southwest when booking your flight. These represent the most popular airlines when flying from Chesapeake to Orlando.

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.

Find Cheap Flights from Chesapeake to Orlando

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Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in February or May, booked 50 days in advance, depart on a Sunday or Saturday and return on a Thursday

Find flight deals from Chesapeake to Orlando

Most accurate provider	FlightHub 3 stars
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Popular in	April
Cheapest in	February
Average price	$253

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Highest demand for flights based on searches. 3% potential increase in price ($6 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 November 2026

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Cheapflights Insights

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

What is the cheapest time of day to fly from C6E to ORL?

It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 25% 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?

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

Reviews of airlines servicing Orlando

Peruse reviews from past customers who have flown with Breeze Airways,Southwest, andDelta 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

8.2

Very good

324 reviews

Reviews

1 / 18

10.0

Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.

Breeze Airways

8.2

Very good

324 reviews

Breeze Airways

8.2

Very good

324 reviews

Reviews

1 / 18

10.0

Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.

Southwest

8.0

Very good

4,220 reviews

Breeze Airways

8.2

Very good

324 reviews

Reviews

1 / 18

10.0

Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.

Delta

7.8

Good

8,697 reviews

Breeze Airways

8.2

Very good

324 reviews

Reviews

1 / 18

10.0

Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.

American Airlines

7.0

Good

12,218 reviews

Breeze Airways

8.2

Very good

324 reviews

Reviews

1 / 18

10.0

Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.

Frontier

5.5

Fair

2,510 reviews

Breeze Airways

8.2

Very good

324 reviews

Reviews

1 / 18

10.0

Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.

Related info for your journey

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 $40 on Frontier. Other airlines that offer cheap prices include Breeze Airways from $59 and Southwest from $88 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 (87%), JetBlue (83%) and Southwest (81%).
What are the cheapest flights from Chesapeake to Orlando?
The cheapest flight price from Chesapeake to Orlando is $64. On average you can expect to pay $225. The most popular route, (Norfolk - Orlando), can usually be booked for $122.
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.

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Top 8 airlines flying from Chesapeake to Orlando

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$66	Average$176	FlexibilityNo cancel fee	On-time62%
Allegiant Air	Cheapest$81	Average$186	FlexibilityNo cancel fee	On-time88%
Delta	Cheapest$88	Average$292	FlexibilityNo cancel fee	On-timeN/A
Breeze Airways	Cheapest$115	Average$247	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$123	Average$329	FlexibilityNo cancel fee	On-time63%
JetBlue	Cheapest$125	Average$263	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$158	Average$352	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$196	Average$561	FlexibilityNo cancel fee	On-time69%

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Cheap flights from Chesapeake, VA to Orlando (ORL)

Find cheap flights from Chesapeake to Orlando with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Chesapeake to Orlando

Most accurate provider

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Popular in

Cheapest in

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Cheapflights Insights

What is the cheapest time of day to fly from C6E to ORL?

It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 25% 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?

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

Reviews of airlines servicing Orlando

Peruse reviews from past customers who have flown with Breeze Airways,Southwest, andDelta 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.

Related info for your journey

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

What are the most reliable airlines from Chesapeake to Orlando?

What are the cheapest flights from Chesapeake to Orlando?

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

How can I find direct flights from Chesapeake to Orlando?

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

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 Chesapeake to Orlando

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to Orlando by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Chesapeake to Orlando by cabin class

Find flights from Chesapeake to Orlando, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Other flights to Orlando

Explore flights to Orlando departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 3, 2026.

Chesapeake and Orlando flights

Browse other Chesapeake and Orlando flight options. Last updated on November 3, 2026.

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Top 8 airlines flying from Chesapeake to Orlando

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