- Must visit
The Charles Hosmer Morse Museum of American Art
Celebrated museum in nearby Winter Park famous for the world’s most comprehensive collection of works by Louis Comfort Tiffany.
Flights from Chesapeake, VA to Orlando, FL depart on average 45 times per day, taking around 2h 6m. Cheap flight tickets for this journey start at $54 (€43) if you book in advance.
There are 1 flights per day. The earliest flight runs at 05:00, the last at 20:22. The fastest flight covers the 644 miles (1037 km) distance in 2h 6m. January is the cheapest month to fly.
Distance 644 miles (1037 km) |
Average flight duration 2h 6m |
Cheapest ticket price $54 (€43) |
Flights per day 45 |
Direct flights 1 |
Fastest flight 2h 6m |
First flight 5:00 AM |
Last flight 8:22 PM |
Cheapest Month Jan |
Cheapest Day Sat |
High Season Jan - Mar |
Low Season Oct - Dec |
Cheapest price
$90
Average price
$634
Fastest journey
2 h 16 m
Average duration
4 h 31 m
Flights per day
27
Distance
1037 km
The best way to find a cheap flight ticket from Chesapeake, VA to Orlando, FL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chesapeake, VA to Orlando, FL will cost around $634 if you buy it on the day, but the cheapest tickets can be found for only $90.
Of the 27 flights that leave Chesapeake, VA for Orlando, FL onFri, Jun 05, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Fri, Jun 05 the direct flights cover the 1037 km distance in an average of 4 h 31 m but if you time it right, some flights will get you there in just 2 h 16 m .
On Fri, Jun 05 the longest flights will take 5 h 48 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
MX418
UA2066 · UA1101
UA3670 · UA1190
UA4760 · UA609
UA4810 · UA689
MX418
UA2066 · UA2206
UA4810 · UA689
UA1524 · UA379
UA3670 · UA1190Omio recommends booking the flight as it is the most popular option from Chesapeake, VA to Orlando, FL among Omio's users. If you are prioritising price take the flight with prices starting from $54. For those with little time consider booking a flight which can get you there in 2h 6m. The ticket price range depends on the travel mode: a flight costs an average of $54, and a train costs an average of $203.
Distance: 644 miles (1037 km)
Most popular Flight | Train | Bus |
|---|---|---|
$126 Average price Cheapest | $247 Average price | $231 Average price |
5h 6m Average total duration Fastest 2h 6m Onboard + 3h 0m Additional time* | 20h 37m Average total duration 20h 7m Onboard + 30m Additional time* | 40h 30m Average total duration 40h 0m Onboard + 30m Additional time* |
Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chesapeake, VA to Orlando, FL:
A flight is $106 (€85) less than a bus for this route with tickets for a bus from Chesapeake, VA to Orlando, FL costing on average $231 (€187).
A flight is $122 (€98) less than a train for this route with tickets for a train from Chesapeake, VA to Orlando, FL costing on average $247 (€200).
Other travel options to Orlando, FL take longer:
Train takes on average 20h 7m.
Bus takes on average 40h 0m.
The table below shows live departures for Chesapeake, VA to Orlando, FL flights for tomorrow, Friday, June 5. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
UA3712 · UA1739 | 5:50 AM Norfolk International Airport | 7h04 | 12:54 PM Orlando International Airport | 1 transfer | |
UA3712 · UA1413 · UA2206 | 5:50 AM Norfolk International Airport | 9h08 | 2:58 PM Orlando International Airport | 2 transfers | |
UA5287 · UA1643 | 6:00 AM Norfolk International Airport | 7h13 | 1:13 PM Orlando International Airport | 1 transfer | |
UA1524 · UA379 | 6:05 AM Norfolk International Airport | 5h18 | 11:23 AM Orlando International Airport | 1 transfer | |
UA1524 · UA1252 · UA1811 | 6:05 AM Norfolk International Airport | 10h50 | 4:55 PM Orlando International Airport | 2 transfers | |
UA2606 · UA2662 | 6:15 AM Norfolk International Airport | 9h49 | 4:04 PM Orlando International Airport | 1 transfer | |
UA2606 · UA2310 | 6:15 AM Norfolk International Airport | 6h45 | 1:00 PM Orlando International Airport | 1 transfer | |
UA2606 · UA1571 | 6:15 AM Norfolk International Airport | 14h14 | 8:29 PM Orlando International Airport | 1 transfer | |
UA2606 · UA496 | 6:15 AM Norfolk International Airport | 11h59 | 6:14 PM Orlando International Airport | 1 transfer | |
UA2270 · UA259 | 8:00 AM Norfolk International Airport | 15h41 | 11:41 PM Orlando International Airport | 1 transfer | |
UA2270 · UA501 | 8:00 AM Norfolk International Airport | 11h39 | 7:39 PM Orlando International Airport | 1 transfer | |
UA2809 · UA1811 | 8:00 AM Norfolk International Airport | 8h55 | 4:55 PM Orlando International Airport | 1 transfer | |
UA2809 · UA2008 | 8:00 AM Norfolk International Airport | 7h03 | 3:03 PM Orlando International Airport | 1 transfer | |
UA3717 · UA1213 | 10:44 AM Norfolk International Airport | 7h13 | 5:57 PM Orlando International Airport | 1 transfer | |
UA3717 · UA2215 | 10:44 AM Norfolk International Airport | 6h19 | 5:03 PM Orlando International Airport | 1 transfer | |
UA2066 · UA2206 | 10:45 AM Norfolk International Airport | 4h13 | 2:58 PM Orlando International Airport | 1 transfer | |
UA2066 · UA2331 · UA1382 | 10:45 AM Norfolk International Airport | 11h10 | 9:55 PM Orlando International Airport | 2 transfers | |
UA2066 · UA1101 | 10:45 AM Norfolk International Airport | 7h14 | 5:59 PM Orlando International Airport | 1 transfer | |
UA4760 · UA609 | 10:48 AM Norfolk International Airport | 7h09 | 5:57 PM Orlando International Airport | 1 transfer | |
B61814 · B6551 | 10:50 AM Norfolk International Airport | 11h09 | 9:59 PM Orlando International Airport | 1 transfer | |
B61814 · B6451 | 10:50 AM Norfolk International Airport | 8h19 | 7:09 PM Orlando International Airport | 1 transfer | |
B61814 · B6317 · B62583 | 10:50 AM Norfolk International Airport | 11h50 | 10:40 PM Orlando International Airport | 2 transfers | |
B61814 · B6317 · B61083 | 10:50 AM Norfolk International Airport | 12h47 | 11:37 PM Orlando International Airport | 2 transfers | |
B61799 · B61948 | 12:15 PM Norfolk International Airport | 9h25 | 9:40 PM Orlando International Airport | 1 transfer | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Discover the best of Orlando — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Orlando trip today.
Celebrated museum in nearby Winter Park famous for the world’s most comprehensive collection of works by Louis Comfort Tiffany.
Established art museum in Loch Haven Park with American art, African art, and rotating exhibitions; a leading cultural stop in the city.
Well-regarded history museum in a restored courthouse covering Central Florida history, tourism, citrus, aviation, and local communities.
Downtown Orlando’s most famous urban park, popular for skyline views, the lake loop, swan boats, events, and easy walking.
Orlando’s best-known tourist corridor, lined with attractions, entertainment complexes, and highly photographed nightlife spots.
Charming, walkable main street area just north of Orlando, loved for its brick streets, boutique atmosphere, and polished local feel.
A pressed sandwich with roast pork, ham, Swiss cheese, pickles, and mustard on Cuban bread. It is a Central Florida staple shaped by the region’s Cuban influences.
Fried alligator tail pieces, usually served with a dipping sauce. This is a classic Florida novelty dish tied to the state’s wetlands and Southern cooking traditions.
A sandwich made with local grouper, often grilled, blackened, or fried. It is one of the most recognizable seafood dishes in Central Florida.
Orlando’s flagship fine-dining destination at Walt Disney World, known for tasting menus, polished service, and special-occasion dining.
Beloved neighborhood bakery and diner famous for Southern comfort food, biscuits, and outstanding pies and cakes.
A well-known Winter Park gastropub near Orlando, celebrated for refined American cooking, strong charcuterie, and a lively upscale-casual atmosphere.
Moderate overall. Theme parks and resort areas are pricey, but casual dining and chain hotels can be reasonable outside peak seasons.
Tip 18-20% at restaurants if service is not included. Tip bartenders USD 1-2 per drink, taxis and rideshares 10-15%, hotel staff USD 1-5, and round up for cafes if desired.
Find answers to the most common questions about traveling from Chesapeake, VA to Orlando, FL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Orlando, FL, this guide helps you travel smarter and with confidence.

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