Cheap flights from Chesapeake, VA to Orlando (ORL)
RIC — ORL
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chesapeake to Orlando are usually found in February or January, booked 86 days in advance, depart on a Sunday or Saturday and return on a Thursday
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 September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Popular in | April |
Cheapest in | February |
Average price | $234 |
Cheapflights Insights
Everything you need to know about your flight from Chesapeake to Orlando
Prices
Airlines
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 23, 2026.
It’s typically best to fly out from Chesapeake to Orlando in the afternoon. Doing so could potentially save you 33% 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 September 19, 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 September 23, 2026.
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.
Overall
8.2
Boarding
8.4
Comfort
8.2
Crew
8.8
Entertainment
6.7
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Boarding
8.4
Comfort
8.2
Crew
8.8
Entertainment
6.7
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Boarding
8.4
Comfort
8.2
Crew
8.8
Entertainment
6.7
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Boarding
8.4
Comfort
8.2
Crew
8.8
Entertainment
6.7
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Boarding
8.4
Comfort
8.2
Crew
8.8
Entertainment
6.7
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Boarding
8.4
Comfort
8.2
Crew
8.8
Entertainment
6.7
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
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.
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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 September 23, 2026.
Chesapeake and Orlando flights
Browse other Chesapeake and Orlando flight options. Last updated on September 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$60 | Average$165 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$72 | Average$259 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$81 | Average$206 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$93 | Average$291 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$112 | Average$249 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$112 | Average$326 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$158 | Average$344 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$558 | FlexibilityNo cancel fee | On-time69% |