The cheapest and fastest trains from Chesapeake, VA to Orlando, FL
Cheapest price
$291
Average price
$291
Fastest journey
22 h 39 m
Average duration
22 h 39 m
Trains per day
1
Distance
1037 km
The best way to find a cheap train 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 $291 if you buy it on the day, but the cheapest tickets can be found for only $291.
Of the 1 trains that leave Chesapeake, VA for Orlando, FL on Thu, Mar 05, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Thu, Mar 05 the direct trains cover the 1037 km distance in an average of 22 h 39 m but if you time it right, some trains will get you there in just 22 h 39 m .
On Thu, Mar 05 the slowest trains will take 22 h 39 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.


Travel Information
Compare train, bus, and flight for Chesapeake, VA to Orlando, FL
Omio 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 $34. 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 $34, and a bus costs an average of $131.
Distance: 644 miles (1037 km)
Compare train with
| Train | Most popular Flight | Bus |
|---|---|---|
$205 Average price | $115 Average price Cheapest | $224 Average price |
20h 37m Average total duration 20h 7m Onboard + 30m Additional time* | 5h 6m Average total duration Fastest 2h 6m Onboard + 3h 0m Additional time* | 41h 8m Average total duration 40h 38m Onboard + 30m Additional time* |
Direct Options | Direct Options | Direct Options |
Live departures
Chesapeake, VA to Orlando, FL train times
The table below shows live departures for Chesapeake, VA to Orlando, FL trains for today, Wednesday, March 4. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 12:59 PM Chesapeake, VA | 21h08 | 10:07 AM Orlando, FL | 1 transfer | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Chesapeake, VA to Orlando, FL by train, bus, or flight
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.
Mar 05
Mar 06
Mar 07
Mar 08
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Mar 11
Journey information
Overview: Train from Chesapeake, VA to Orlando, FL
Trains from Chesapeake, VA to Orlando, FL run on average 5 times per day, taking around 20h 7m. Cheap train tickets for this journey start at $118 (€96) but you can travel from only $34 (€27) by flight.
The earliest train runs at 11:14, the last at 19:25. The fastest train covers the 644 miles (1037 km) distance in 22h 39m.
Distance 644 miles (1037 km) |
Average train duration 20h 7m |
Cheapest ticket price $118 (€96) |
Trains per day 5 |
Fastest train 22h 39m |
First train 11:14 |
Last train 19:25 |
Train companies: Amtrak from Chesapeake, VA to Orlando, FL trainsAmtrak trains will get you between Chesapeake, VA and Orlando, FL from $34 (€27). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from Chesapeake, VA to Orlando, FL
Find answers to the most common questions about traveling from Chesapeake, VA to Orlando, FL by train. 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 train, the cheapest option, or tips for making the most of your visit at Orlando, FL, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from Chesapeake, VA to Orlando, FL
- 6:00 AM - 10:00 PM Monday - Sunday
- Parking is available subject to city ordinances and availability.
- Mary Mary Bar
- The Boheme
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- Orlando World Center Marriott
- Grand Bohemian Hotel Orlando
- Aloft Orlando Downtown
- Located in the main hall
- Located in the main hall
- Free
- Hall 1: main entrance, ticket office, and waiting area
- Hall 2: access to platforms
- Bus: LYNX services available
- SunRail: Available
Most popular train connections from Chesapeake, VA
More options for your journey from Chesapeake, VA to Orlando, FL
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