There are 5 ways to get from Chesapeake to Kissimmee by plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Orlando
best- Fly from Norfolk International Airport (ORF) to Orlando (MCO)plane ORF - MCO
3h 45m$122–409Train (Amtrak)
- Take the train from Norfolk to Petersburg Amtrak Stationtrain Northeast Regional
- Take the train from Petersburg Amtrak Station to Kissimmee Amtrak Stationtrain Silver Meteor / ...
17h 39m$211–509Bus
- Take the bus from Norfolk to Raleigh Bus Stationbus Greyhound US0654s
- Take the bus from Raleigh Bus Station to Orlando Bus Stationbus FlixBus N2472
20h 36m$125–196Drive 756.5 mi
- Drive from Chesapeake to Kissimmeecar 756.5 mi
13h 6m$139–200Fly to Tampa, train
- Fly from Norfolk International Airport (ORF) to Tampa (TPA)plane ORF - TPA
- Take the train from Tampa to Kissimmee Amtrak Stationtrain
6h 14m$192–544
Chesapeake to Kissimmee by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Chesapeake to Kissimmee is to bus which costs $120 - $200 and takes 20h 36m.
The fastest way to get from Chesapeake to Kissimmee is to fly which takes 3h 45m and costs $120 - $410.
No, there is no direct bus from Chesapeake to Kissimmee. However, there are services departing from Dntc and arriving at N Main St & W Cypress St via Military Circle Mall, Norfolk, Raleigh Bus Station, Orlando Bus Station and Florida Mall. The journey, including transfers, takes approximately 20h 36m.
No, there is no direct train from Chesapeake to Kissimmee station. However, there are services departing from Norfolk and arriving at Kissimmee Amtrak Station via Petersburg Amtrak Station. The journey, including transfers, takes approximately 17h 39m.
The distance between Chesapeake and Kissimmee is 686 miles. The road distance is 760.9 miles.
The best way to get from Chesapeake to Kissimmee without a car is to train which takes 17h 39m and costs $210 - $550.
It takes approximately 3h 45m to get from Chesapeake to Kissimmee, including transfers.
Chesapeake to Kissimmee bus services, operated by Greyhound USA, depart from Norfolk station.
Chesapeake to Kissimmee train services, operated by Amtrak, depart from Norfolk station.
The best way to get from Chesapeake to Kissimmee is to fly which takes 3h 45m and costs $120 - $410. Alternatively, you can train, which costs $210 - $550 and takes 17h 39m, you could also bus, which costs $120 - $200 and takes 20h 36m.
What companies run services between Chesapeake, City of Chesapeake, VA, USA and Kissimmee, FL, USA?
Breeze Airways, Frontier Airlines, and three other airlines fly from Norfolk International Airport (ORF) to Orlando (MCO) every 4 hours. Alternatively, you can take a train from Norfolk to Kissimmee Amtrak Station via Petersburg Amtrak Station in around 17h 39m.
- Website
- southwest.com
Flights from Norfolk International Airport to Orlando
- Ave. Duration
- 2h 3m
- When
- Every day
- Estimated price
- $75–430
Flights from Norfolk International Airport to Orlando via Baltimore
- Ave. Duration
- 4h 28m
- When
- Every day
- Estimated price
- $95–490
Flights from Norfolk International Airport to Tampa via Baltimore
- Ave. Duration
- 4h 52m
- When
- Every day
- Estimated price
- $100–550
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Norfolk to Petersburg Amtrak Station
- Ave. Duration
- 1h 24m
- Frequency
- Twice daily
- Estimated price
- $20–50
- Website
- Amtrak
Train from Petersburg Amtrak Station to Kissimmee Amtrak Station
- Ave. Duration
- 15h 15m
- Frequency
- Twice daily
- Estimated price
- $190–460
- Website
- Amtrak
Train from Tampa to Kissimmee Amtrak Station
- Ave. Duration
- 1h 18m
- Frequency
- Once daily
- Estimated price
- $18–45
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Norfolk to Raleigh Bus Station
- Ave. Duration
- 4h 30m
- Frequency
- Twice daily
- Estimated price
- $30–50
- Website
- Greyhound
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide
Need to know: Greyhound
Read the travel guide
Booking & Getting There
Chesapeake to Kissimmee bus services, operated by Greyhound USA, arrive at Raleigh Bus Station.
Chesapeake to Kissimmee train services, operated by Amtrak, arrive at Petersburg Amtrak Station.
Yes, the driving distance between Chesapeake to Kissimmee is 761 miles. It takes approximately 13h 6m to drive from Chesapeake to Kissimmee.
Book your Chesapeake to Kissimmee train tickets online with Omio.
There are 10008+ hotels available in Kissimmee.





