There are 5 ways to get from Chesapeake to Kissimmee by plane, train (Amtrak), bus (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 49m$132–519Train (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$277–605Bus
- Take the bus from Norfolk to Richmondbus FlixBus N2601
- Take the bus from Richmond to Orlando Bus Stationbus FlixBus N2472 / ...
21h 3m$208–309Drive 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 8m$218–639
Chesapeake to Kissimmee by train (Amtrak)
Questions & Answers
The cheapest way to get from Chesapeake to Kissimmee is to drive which costs $130 - $200 and takes 13h 6m.
The fastest way to get from Chesapeake to Kissimmee is to fly which takes 3h 49m and costs $130 - $550.
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, Richmond, Orlando Bus Station and Florida Mall. The journey, including transfers, takes approximately 21h 3m.
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 $270 - $650.
It takes approximately 3h 49m to get from Chesapeake to Kissimmee, including transfers.
Chesapeake to Kissimmee bus services, operated by Flixbus 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 49m and costs $130 - $550. Alternatively, you can train, which costs $270 - $650 and takes 17h 39m, you could also bus, which costs $200 - $310 and takes 21h 3m.
What companies run services between Chesapeake, City of Chesapeake, VA, USA and Kissimmee, FL, USA?
Frontier Airlines, Breeze Airways, and three other airlines fly from Norfolk International Airport (ORF) to Orlando (MCO) 5 times a day. 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 8m
- When
- Every day
- Estimated price
- $70–380
Flights from Norfolk International Airport to Orlando via Baltimore
- Ave. Duration
- 4h 26m
- When
- Tuesday to Saturday
- Estimated price
- $95–440
Flights from Norfolk International Airport to Tampa via Baltimore
- Ave. Duration
- 4h 41m
- When
- Every day
- Estimated price
- $100–490
- Website
- aa.com
Flights from Norfolk International Airport to Orlando via Charlotte
- Ave. Duration
- 4h 20m
- When
- Sunday
- Estimated price
- $80–400
Flights from Norfolk International Airport to Tampa via Charlotte
- Ave. Duration
- 4h 44m
- When
- Every day
- Estimated price
- $90–450
Flights from Norfolk International Airport to Tampa via Miami
- Ave. Duration
- 4h 31m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $100–490
- Website
- flybreeze.com
Flights from Norfolk International Airport to Orlando
- Ave. Duration
- 2h 14m
- When
- Thursday, Saturday, Sunday, Wednesday, Monday, and Friday
- Estimated price
- $100–550
Flights from Norfolk International Airport to Tampa
- Ave. Duration
- 2h 13m
- When
- Every day
- Estimated price
- $160–550
- Website
- delta.com
Flights from Norfolk International Airport to Tampa via Atlanta
- Ave. Duration
- 4h 33m
- When
- Every day
- Estimated price
- $100–480
- Website
- flyfrontier.com
Flights from Norfolk International Airport to Orlando
- Ave. Duration
- 2h 13m
- When
- Every day
- Estimated price
- $70–300
- Website
- united.com
Flights from Norfolk International Airport to Orlando via Washington Dulles
- Ave. Duration
- 4h 18m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $90–440
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Norfolk to Petersburg Amtrak Station
- Ave. Duration
- 1h 24m
- Frequency
- Twice daily
- Estimated price
- $27–55
- Website
- https://www.amtrak.com/home.html
Train from Petersburg Amtrak Station to Kissimmee Amtrak Station
- Ave. Duration
- 15h 15m
- Frequency
- Twice daily
- Estimated price
- $250–550
- Website
- https://www.amtrak.com/home.html
Train from Tampa to Kissimmee Amtrak Station
- Ave. Duration
- 1h 18m
- Frequency
- Once daily
- Estimated price
- $24–50
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Norfolk to Richmond
- Ave. Duration
- 1h 55m
- Frequency
- Once daily
- Estimated price
- $15–26
- Schedules at
- flixbus.com
Bus from Richmond to Orlando Bus Station
- Ave. Duration
- 14h 25m
- Frequency
- Once daily
- Estimated price
- $120–200
- Schedules at
- flixbus.com
- Phone
- +1-858-800-8898
- Website
- jeffersonlines.com
Bus from Norfolk to Richmond
- Ave. Duration
- 2h
- Frequency
- 6 times a week
- Estimated price
- $30–45
- Book at
- https://www.jeffersonlines.com
- Adult
- $30–45
Bus from Richmond to Orlando Bus Station
- Ave. Duration
- 14h 25m
- Frequency
- Once daily
- Estimated price
- $160–240
- Book at
- https://www.jeffersonlines.com
- Adult
- $160–240
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More Questions & Answers
Chesapeake to Kissimmee bus services, operated by Flixbus USA, arrive at Richmond 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 9444+ hotels available in Kissimmee.







