How much is the train ticket from Kissimmee to Chicago?

The cheapest train tickets from Kissimmee to Chicago start from $133. The average price for this train route is around $437. 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 20h, 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 12:57pm. And the latest train departs at 6:10pm.

Train Kissimmee to Chicago from $261 | Refundable Tickets

Next train departures

Next departures for Kissimmee to Chicago on December 13
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	12:57pm	SunRail Station	1d 20h	8:45am	Chicago (Union Station), IL	No tags
Train	12:57pm	SunRail Station	1d 20h	8:45am	Chicago (Union Station), IL	No tags
Train	12:57pm	SunRail Station	1d 22h	10:00am	Chicago (Union Station), IL	No tags

Next departures for Kissimmee to Chicago on December 14
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	12:57pm	SunRail Station	1d 20h	8:45am	Chicago (Union Station), IL	No tags
Train	12:57pm	SunRail Station	1d 20h	8:45am	Chicago (Union Station), IL	No tags
Train	12:57pm	SunRail Station	1d 22h	10:12am	Chicago (Union Station), IL	No tags

Next departures for Kissimmee to Chicago on December 15
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	12:57pm	SunRail Station	1d 20h	8:45am	Chicago (Union Station), IL	No tags
Train	12:57pm	SunRail Station	1d 20h	8:45am	Chicago (Union Station), IL	No tags
Train	12:57pm	SunRail Station	1d 22h	10:12am	Chicago (Union Station), IL	No tags

Next departures for Kissimmee to Chicago on December 16
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	12:57pm	SunRail Station	1d 20h	8:45am	Chicago (Union Station), IL	No tags
Train	12:57pm	SunRail Station	1d 20h	8:45am	Chicago (Union Station), IL	No tags
Train	12:57pm	SunRail Station	1d 22h	10:12am	Chicago (Union Station), IL	No tags

Next departures for Kissimmee to Chicago on December 17
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	12:57pm	SunRail Station	1d 20h	8:45am	Chicago (Union Station), IL	No tags
Train	12:57pm	SunRail Station	1d 20h	8:45am	Chicago (Union Station), IL	No tags
Train	12:57pm	SunRail Station	1d 22h	10:12am	Chicago (Union Station), IL	No tags

Last refresh of the prices: Today at 9:46 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 the good way to reach Chicago. The journey takes about 1 day, 9 hours 20 minutes and with fares starting at just $113, it presents an excellent value for a comfortable ride.

5bus per day

1d 9hAverage Duration

987 milesDistance

40kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average Price$113 - $475	Average Duration1d 9h	CO₂ emissions 40kg CO₂e
Train	Average Price$133 - $4,221	Average Duration1d 20h	CO₂ emissions 147kg CO₂e

Train Companies

Amtrak

4/55,638 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5638 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 $133

Train and bus companies in US: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 $133. The average price for this train route is around $437. 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 20h, 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 12:57pm. 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

12/09

$328

12/10

$398

Today

$398

12/12

$270

12/13

$270

12/14

$328

12/15

$270

12/16

$328

The cheapest trip from Kissimmee to Chicago was searched and found on Dec 12, 2025 with a price of $270

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 $270 to $3,152 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 $270 which is on 2025-12-12.