There are 8 ways to get from Naperville to Kissimmee by train, plane, bus (Greyhound, Flixbus), train (Amtrak), or car
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Train to Chicago Midway International Airport, fly to Orlando
best- Take the train from Naperville to Chicago Union Stationtrain
- Fly from Chicago Midway International Airport (MDW) to Orlando (MCO)plane MDW - MCO
7h 5m$191–477Train to Chicago O'Hare International Airport, fly to Orlando
cheapest- Take the train from Naperville to Chicago Union Stationtrain
- Fly from Chicago O'Hare International Airport (ORD) to Orlando (MCO)plane ORD - MCO
7h 21m$121–437Bus
- Take the bus from Chicago Bus Station to Atlanta Bus Stationbus Greyhound US0100
- Take the bus from Atlanta Bus Station to Orlandobus FlixBus 2415
31h 23m$188–319Train
- Take the train from Naperville to Chicago Union Stationtrain Bnsf
- Take the train from Chicago Union Station to Kissimmee Amtrak Stationtrain Floridian
41h 2m$955–1,506Drive 1,132 mi
- Drive from Naperville to Kissimmeecar 1,132 mi
20h 18m$200–289Train to Chicago Midway International Airport, fly to Tampa, train
- Take the train from Naperville to Chicago Union Stationtrain
- Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane MDW - TPA
- Take the train from Tampa to Kissimmee Amtrak Stationtrain
9h 15m$153–482Train to Chicago O'Hare International Airport, fly to Tampa, train
- Take the train from Naperville to Chicago Union Stationtrain
- Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane ORD - TPA
- Take the train from Tampa to Kissimmee Amtrak Stationtrain
9h 26m$163–442Train, train to General Mitchell International Airport, fly to Orlando
- Take the train from Naperville to Chicago Union Stationtrain
- Take the train from Chicago Union Station to Milwaukeetrain
- Fly from General Mitchell International Airport (MKE) to Orlando (MCO)plane MKE - MCO
9h 18m$466–1,201
Naperville to Kissimmee by bus
Comparing Your Travel Options
The cheapest way to get from Naperville to Kissimmee is to train and fly which costs $150 - $490 and takes 9h 15m.
The fastest way to get from Naperville to Kissimmee is to train and fly which takes 7h 5m and costs $190 - $480.
No, there is no direct bus from Naperville to Kissimmee. However, there are services departing from Washington St & Ogden Ave and arriving at N Main St & W Cypress St via Yorktown Center, 54th/Cermak Pink Line Station, Chicago Bus Station, Atlanta Bus Station and Florida Mall. The journey, including transfers, takes approximately 31h 23m.
No, there is no direct train from Naperville to Kissimmee station. However, there are services departing from Naperville and arriving at Kissimmee Amtrak Station via Chicago Union Station. The journey, including transfers, takes approximately 41h 2m.
The distance between Naperville and Kissimmee is 1057 miles. The road distance is 1138.6 miles.
The best way to get from Naperville to Kissimmee without a car is to bus which takes 31h 23m and costs $180 - $320.
It takes approximately 7h 5m to get from Naperville to Kissimmee, including transfers.
Naperville to Kissimmee bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Naperville to Kissimmee train services, operated by Metra, depart from Naperville station.
The best way to get from Naperville to Kissimmee is to bus which takes 31h 23m and costs $180 - $320. Alternatively, you can train, which costs $950 - $1,600 and takes 41h 2m.
What companies run services between Naperville, IL, USA and Kissimmee, FL, USA?
You can take a bus from Washington St & Ogden Ave to N Main St & W Cypress St via Yorktown Center, 54th/Cermak Pink Line Station, Jefferson & Harrison, Chicago Bus Station, Atlanta Bus Station, Orlando, and Florida Mall in around 31h 23m. Alternatively, you can take a train from Naperville to Kissimmee Amtrak Station via Chicago Union Station in around 41h 2m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Orlando
- Ave. Duration
- 2h 37m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Orlando via Nashville
- Ave. Duration
- 4h 20m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Orlando via Louisville
- Ave. Duration
- 4h 30m
- When
- Tuesday and Wednesday
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Tampa
- Ave. Duration
- 2h 37m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Tampa via Indianapolis
- Ave. Duration
- 4h 25m
- When
- Saturday
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Tampa via Birmingham
- Ave. Duration
- 4h 25m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $140–700
Flights from Chicago Midway International Airport to Tampa via Atlanta
- Ave. Duration
- 4h 55m
- When
- Tuesday and Wednesday
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Tampa via Nashville
- Ave. Duration
- 5h
- When
- Tuesday and Wednesday
- Estimated price
- $130–700
Flights from General Mitchell International Airport to Orlando
- Ave. Duration
- 2h 48m
- When
- Every day
- Estimated price
- $140–700
Flights from General Mitchell International Airport to Orlando via St. Louis
- Ave. Duration
- 4h 35m
- When
- Saturday
- Estimated price
- $150–750
- Website
- delta.com
Flights from Chicago Midway International Airport to Orlando via Atlanta
- Ave. Duration
- 4h 27m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago O'Hare International Airport to Orlando via Atlanta
- Ave. Duration
- 4h 33m
- When
- Every day
- Estimated price
- $80–410
Flights from Chicago Midway International Airport to Tampa via Atlanta
- Ave. Duration
- 4h 58m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago O'Hare International Airport to Tampa via Atlanta
- Ave. Duration
- 4h 37m
- When
- Every day
- Estimated price
- $85–420
Flights from General Mitchell International Airport to Orlando
- Ave. Duration
- 3h 2m
- When
- Saturday
- Estimated price
- $140–700
Flights from General Mitchell International Airport to Orlando via Atlanta
- Ave. Duration
- 4h 44m
- When
- Every day
- Estimated price
- $140–700
- Website
- united.com
Flights from Chicago O'Hare International Airport to Orlando
- Ave. Duration
- 2h 52m
- When
- Every day
- Estimated price
- $80–410
Flights from Chicago O'Hare International Airport to Tampa
- Ave. Duration
- 2h 55m
- When
- Every day
- Estimated price
- $85–420
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Orlando
- Ave. Duration
- 2h 49m
- When
- Every day
- Estimated price
- $80–410
Flights from Chicago O'Hare International Airport to Tampa
- Ave. Duration
- 2h 47m
- When
- Every day
- Estimated price
- $85–420
- Website
- flyfrontier.com
Flights from Chicago Midway International Airport to Orlando
- Ave. Duration
- 2h 43m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- $180–460
Flights from Chicago O'Hare International Airport to Orlando
- Ave. Duration
- 2h 59m
- When
- Every day
- Estimated price
- $95–350
Flights from Chicago O'Hare International Airport to Tampa
- Ave. Duration
- 2h 45m
- When
- Every day
- Estimated price
- $110–360
Flights from General Mitchell International Airport to Orlando
- Ave. Duration
- 2h 51m
- When
- Thursday
- Estimated price
- $180–600
- Website
- suncountry.com
Flights from General Mitchell International Airport to Orlando
- Ave. Duration
- 2h 55m
- When
- Thursday
- Estimated price
- $140–700
- Phone
- +1 312-696-3872
- Website
- Metra
Train from Naperville to Chicago Union Station
- Ave. Duration
- 1h 4m
- Frequency
- Hourly
- Estimated price
- $5–6
- Website
- Metra
- Adult
- $5–6
Train from Naperville to Chicago Union Station
- Ave. Duration
- 1h 4m
- Frequency
- Hourly
- Estimated price
- $5–6
- Website
- Metra
- Adult
- $5–6
Train from Naperville to Chicago Union Station
- Ave. Duration
- 1h 4m
- Frequency
- Hourly
- Estimated price
- $5–6
- Website
- Metra
- Adult
- $5–6
Train from Naperville to Chicago Union Station
- Ave. Duration
- 1h 4m
- Frequency
- Hourly
- Estimated price
- $5–6
- Website
- Metra
- Adult
- $5–6
Train from Naperville to Chicago Union Station
- Ave. Duration
- 1h 4m
- Frequency
- Hourly
- Estimated price
- $5–6
- Website
- Metra
- Adult
- $5–6
Train from Naperville to Chicago Union Station
- Ave. Duration
- 1h 4m
- Frequency
- Hourly
- Estimated price
- $5–6
- Website
- Metra
- Adult
- $5–6
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Kissimmee Amtrak Station
- Ave. Duration
- 38h 58m
- Frequency
- Once daily
- Estimated price
- $950–1,500
- Website
- Amtrak
Train from Tampa to Kissimmee Amtrak Station
- Ave. Duration
- 1h 18m
- Frequency
- Once daily
- Estimated price
- $40–65
- Website
- Amtrak
Train from Tampa to Kissimmee Amtrak Station
- Ave. Duration
- 1h 18m
- Frequency
- Once daily
- Estimated price
- $40–65
- Website
- Amtrak
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $45–75
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Chicago Bus Station to Atlanta Bus Station
- Ave. Duration
- 16h 5m
- Frequency
- 4 times a day
- Estimated price
- $130–200
- Website
- Greyhound
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago Bus Station to Atlanta Bus Station
- Ave. Duration
- 16h
- Frequency
- 3 times a day
- Estimated price
- $110–170
- Schedules at
- Flixbus USA
Bus from Atlanta Bus Station to Orlando
- Ave. Duration
- 9h 9m
- Frequency
- 6 times a week
- Estimated price
- $70–110
- Schedules at
- Flixbus USA
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Booking & Getting There
Naperville to Kissimmee bus services, operated by Greyhound USA, arrive at Atlanta Bus Station.
Kissimmee is 1h ahead of Naperville. It is currently 5:45 AM in Naperville and 6:45 AM in Kissimmee.
Naperville to Kissimmee train services, operated by Metra, arrive at Chicago Union Station.
Yes, the driving distance between Naperville to Kissimmee is 1139 miles. It takes approximately 20h 18m to drive from Naperville to Kissimmee.
Book your Naperville to Kissimmee train tickets online with Omio.
There are 34+ hotels available in Kissimmee.








