There are 9 ways to get from Chipley to Kissimmee by car, plane, taxi, bus, 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.
Drive to Pensacola International Airport, fly to Orlando
best- Drive from Chipley to Pensacola-Airport-PNScar
- Fly from Pensacola International Airport (PNS) to Orlando (MCO)plane PNS - MCO
4h 55m$104–265Drive 349 mi
cheapest- Drive from Chipley to Kissimmeecar 349 mi
5h 40m$64–92Taxi, bus via Office Ct & Sand Lake Sunrail
- Take the taxi from Chipley to Dothantaxi
- Take the bus from Dothan to Tallahasseebus
- Take the bus from Tallahassee - FSU - Old St Augustine at Intramural Field to Orlando - RedCoach Station, FLbus
10h 4m$97–134Taxi to Northwest Florida Beaches International Airport, fly to Orlando
- Take the taxi from Chipley to Northwest Florida Beaches International Airport (ECP)taxi
- Fly from Northwest Florida Beaches International Airport (ECP) to Orlando (MCO)plane ECP - MCO
6h 14m$207–588Taxi to Dothan Regional Airport, fly to Orlando
- Take the taxi from Chipley to Dothan Regional Airport (DHN)taxi
- Fly from Dothan Regional Airport (DHN) to Orlando (MCO)plane DHN - MCO
6h 20m$83–426Drive to Destin–Fort Walton Beach Airport, fly to Orlando
- Drive from Chipley to Destin–Fort Walton Beach Airport (VPS)car
- Fly from Destin–Fort Walton Beach Airport (VPS) to Orlando (MCO)plane VPS - MCO
6h 42m$93–456Drive to Pensacola International Airport, fly to Tampa, train
- Drive from Chipley to Pensacola-Airport-PNScar
- Fly from Pensacola International Airport (PNS) to Tampa (TPA)plane PNS - TPA
- Take the train from Tampa to Kissimmee Amtrak Stationtrain
6h 56m$146–550Taxi, bus
- Take the taxi from Chipley to Dothantaxi
- Take the bus from Dothan to Tallahasseebus
- Take the bus from Tallahassee - FSU - Old St Augustine at Intramural Field to Kissimmee -1471 East Osceola Parkwaybus
10h 57m$95–135Taxi, bus via John Young Pkwy & Amelia St
- Take the taxi from Chipley to Dothantaxi
- Take the bus from Dothan to Tallahasseebus
- Take the bus from Tallahassee to Orlando Bus Stationbus
- Take the bus from N Garland Ave & W Amelia St to N Central Ave & W Cherry Stbus 18
12h 2m$73–108
Pensacola International Airport (PNS) to Orlando (MCO) flights
Comparing Your Travel Options
The cheapest way to get from Chipley to Kissimmee is to drive which costs $60 - $95 and takes 5h 40m.
The fastest way to get from Chipley to Kissimmee is to drive and fly which takes 4h 55m and costs $100 - $270.
The distance between Chipley and Kissimmee is 512 miles. The road distance is 351.1 miles.
The best way to get from Chipley to Kissimmee without a car is to taxi and bus via Office Ct & Sand Lake Sunrail which takes 10h 4m and costs $95 - $140.
It takes approximately 4h 55m to get from Chipley to Kissimmee, including transfers.
Kissimmee is 1h ahead of Chipley. It is currently 12:05 AM in Chipley and 1:05 AM in Kissimmee.
Yes, the driving distance between Chipley to Kissimmee is 351 miles. It takes approximately 5h 40m to drive from Chipley to Kissimmee.
There are 10128+ hotels available in Kissimmee.
What companies run services between Chipley, FL, USA and Kissimmee, FL, USA?
There is no direct connection from Chipley to Kissimmee. However, you can drive to Pensacola-Airport-PNS airport, fly to Orlando (MCO), walk to Orlando International Airport, take the line 42 bus to Office Ct & Sand Lake Sunrail, walk to Sand Lake Road, then take the train to Kissimmee. Alternatively, you can take the taxi to Dothan, take the bus to Tallahassee, walk to C.K. Steele Plaza Gate 1, take the bus to Florida State University 1st Circle, walk to Tallahassee - FSU - Old St Augustine at Intramural Field, take the bus to Orlando - RedCoach Station, FL, take the line 42 bus to Office Ct & Sand Lake Sunrail, walk to Sand Lake Road, then take the train to Kissimmee.
- Website
- delta.com
Flights from Pensacola International Airport to Orlando via Atlanta
- Ave. Duration
- 3h 51m
- When
- Every day
- Estimated price
- $75–420
Flights from Northwest Florida Beaches International Airport to Orlando via Atlanta
- Ave. Duration
- 4h 10m
- When
- Every day
- Estimated price
- $75–430
Flights from Dothan Regional Airport to Orlando via Atlanta
- Ave. Duration
- 4h 22m
- When
- Every day
- Estimated price
- $70–410
Flights from Destin–Fort Walton Beach Airport to Orlando via Atlanta
- Ave. Duration
- 4h 8m
- When
- Every day
- Estimated price
- $75–430
Flights from Pensacola International Airport to Tampa via Atlanta
- Ave. Duration
- 3h 37m
- When
- Every day
- Estimated price
- $80–450
- Website
- southwest.com
Flights from Pensacola International Airport to Orlando
- Ave. Duration
- 1h 30m
- When
- Monday to Friday
- Estimated price
- $55–360
Flights from Northwest Florida Beaches International Airport to Orlando via Nashville
- Ave. Duration
- 5h 36m
- When
- Every day
- Estimated price
- $100–500
Flights from Northwest Florida Beaches International Airport to Orlando via Houston Hobby Apt
- Ave. Duration
- 5h 20m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $120–600
Flights from Northwest Florida Beaches International Airport to Orlando via St. Louis
- Ave. Duration
- 6h 35m
- When
- Saturday
- Estimated price
- $130–650
Flights from Destin–Fort Walton Beach Airport to Orlando via Nashville
- Ave. Duration
- 5h 25m
- When
- Every day
- Estimated price
- $100–500
- Website
- aa.com
Flights from Northwest Florida Beaches International Airport to Orlando via Charlotte
- Ave. Duration
- 4h 41m
- When
- Every day
- Estimated price
- $90–480
Flights from Destin–Fort Walton Beach Airport to Orlando via Charlotte
- Ave. Duration
- 5h
- When
- Saturday, Thursday, Friday, Sunday, Monday, and Wednesday
- Estimated price
- $95–490
Flights from Destin–Fort Walton Beach Airport to Orlando via Miami
- Ave. Duration
- 7h 54m
- When
- Saturday
- Estimated price
- $80–440
- Website
- flybreeze.com
Flights from Pensacola International Airport to Orlando
- Ave. Duration
- 1h 30m
- When
- Every day
- Estimated price
- $80–230
Flights from Pensacola International Airport to Tampa
- Ave. Duration
- 1h 23m
- When
- Every day
- Estimated price
- $150–950
- Website
- united.com
Flights from Northwest Florida Beaches International Airport to Orlando via Houston
- Ave. Duration
- 6h 29m
- When
- Every day
- Estimated price
- $120–600
- Website
- flyfrontier.com
Flights from Pensacola International Airport to Orlando
- Ave. Duration
- 1h 37m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $100–390
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Tampa to Kissimmee Amtrak Station
- Ave. Duration
- 1h 18m
- Frequency
- Once daily
- Estimated price
- $40–65
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Dothan to Tallahassee
- Ave. Duration
- 1h 45m
- Frequency
- Once daily
- Estimated price
- $17–26
- Website
- Greyhound
Bus from Dothan to Tallahassee
- Ave. Duration
- 1h 45m
- Frequency
- Once daily
- Estimated price
- $17–26
- Website
- Greyhound
Bus from Dothan to Tallahassee
- Ave. Duration
- 1h 45m
- Frequency
- Once daily
- Estimated price
- $17–26
- Website
- Greyhound
Bus from Tallahassee to Orlando Bus Station
- Ave. Duration
- 5h 30m
- Frequency
- Once daily
- Estimated price
- $45–70
- Website
- Greyhound
- Phone
- +1 877 733 0724
- Website
- RedCoach
Bus from Tallahassee - FSU - Old St Augustine at Intramural Field to Orlando - RedCoach Station, FL
- Ave. Duration
- 4h 45m
- Frequency
- 4 times a day
- Estimated price
- $65–90
- Website
- RedCoach
Bus from Tallahassee - FSU - Old St Augustine at Intramural Field to Kissimmee -1471 East Osceola Parkway
- Ave. Duration
- 5h 40m
- Frequency
- Once daily
- Estimated price
- $65–95
- Website
- RedCoach
- Phone
- +1 407-841-5969
- [email protected]
- Website
- Lynx
Bus from N Garland Ave & W Amelia St to N Central Ave & W Cherry St
- Ave. Duration
- 1h 37m
- Frequency
- Hourly
- Website
- Lynx
- Schedules at
- Lynx Routes and Schedules
- Adult One-way
- $0
- Ave. Duration
- 45 min
- Estimated price
- $8–160
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
Need to know: Greyhound
Read the travel guide
Why you should take the train in the US
Read the travel guide












