How much is the train ticket from Kissimmee to Chicago?

The cheapest train tickets from Kissimmee to Chicago start from $192. The average price for this train route is around $344. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.

How long is the train journey from Kissimmee to Chicago?

The average train ride duration from Kissimmee to Chicago is 1d 21h, covering a distance of 1000 miles (1613 km). The quickest train can get you there in 1d 15h and is operated by Amtrak .

Which train operators service the Kissimmee to Chicago route?

Several major train operators operate on this route with 3 trains available per day.

What is the earliest and latest departure time for the train from Kissimmee to Chicago?

The earliest train departs from Kissimmee to Chicago at 11:57am. And the latest train departs at 6:10pm.

Train Kissimmee to Chicago from $184 | Refundable Tickets

Next train departures

Next departures for Kissimmee to Chicago on January 27
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	11:57am	SunRail Station	1d 23h	10:25am	Chicago (Union Station), IL	Cheapest
Train	11:57am	SunRail Station	1d 23h	10:12am	Chicago (Union Station), IL	Fastest
Train	11:57am	SunRail Station	1d 23h	10:12am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 23h	10:25am	Chicago (Union Station), IL	No tags

Next departures for Kissimmee to Chicago on January 28
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	6:10pm	SunRail Station	1d 15h	8:45am	Chicago (Union Station), IL	CheapestFastest
Train	6:10pm	SunRail Station	1d 15h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 23h	10:12am	Chicago (Union Station), IL	No tags

Next departures for Kissimmee to Chicago on January 29
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	6:10pm	SunRail Station	1d 15h	8:45am	Chicago (Union Station), IL	CheapestFastest
Train	6:10pm	SunRail Station	1d 15h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 23h	10:12am	Chicago (Union Station), IL	No tags

Next departures for Kissimmee to Chicago on January 30
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	6:10pm	SunRail Station	1d 15h	8:45am	Chicago (Union Station), IL	CheapestFastest
Train	6:10pm	SunRail Station	1d 15h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 23h	10:12am	Chicago (Union Station), IL	No tags

Next departures for Kissimmee to Chicago on January 31
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	6:10pm	SunRail Station	1d 15h	8:45am	Chicago (Union Station), IL	CheapestFastest
Train	6:10pm	SunRail Station	1d 15h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 23h	10:12am	Chicago (Union Station), IL	No tags

Next departures for Kissimmee to Chicago on February 1
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	6:10pm	SunRail Station	1d 15h	8:45am	Chicago (Union Station), IL	CheapestFastest
Train	6:10pm	SunRail Station	1d 15h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	11:57am	SunRail Station	1d 23h	10:12am	Chicago (Union Station), IL	No tags

Last refresh of the prices: Yesterday at 12:11 PM EST.

Compare 2 ways to go from Kissimmee to Chicago

We recommend taking the bus

Among the sustainable travel choices, the Bus stands out as a good way to reach Chicago. The journey takes about 1 day, 9 hours 20 minutes and with fares starting at just $125, it presents an excellent value for a comfortable ride.

7bus per day

1d 9hAverage Duration

997 milesDistance

40kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average Price$125 - $349	Average Duration1d 9h	CO₂ emissions 40kg CO₂e
Train	Average Price$192 - $2,401	Average Duration1d 21h	CO₂ emissions 147kg CO₂e

Train Companies

Amtrak

4/55,751 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5751 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $192

US train companies:Amtrak, Trenitalia, Renfe, VIA Rail Canada, Amtrak Acela, NS Nederlandse Spoorwegen, Iryo

Frequently asked questions about traveling from Kissimmee to Chicago by train

Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.

How much is the train ticket from Kissimmee to Chicago?
The cheapest train tickets from Kissimmee to Chicago start from $192. The average price for this train route is around $344. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the train journey from Kissimmee to Chicago?
The average train ride duration from Kissimmee to Chicago is 1d 21h, covering a distance of 1000 miles (1613 km). The quickest train can get you there in 1d 15h and is operated by Amtrak.
Which train operators service the Kissimmee to Chicago route?
Several major train operators operate on this route with 3 trains available per day.
What is the earliest and latest departure time for the train from Kissimmee to Chicago?
The earliest train departs from Kissimmee to Chicago at 11:57am. And the latest train departs at 6:10pm.

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

01/25

No data

01/26

$2,318

Today

$458

01/28

$270

01/29

$226

01/30

$226

01/31

$184

02/01

$226

The cheapest trip from Kissimmee to Chicago was searched and found on Jan 31, 2026 with a price of $184

To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Kissimmee to Chicago, as early as possible.

You can expect to pay from $184 to $2,318 for a train ticket from Kissimmee to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $184 which is on 2026-01-31.