How much does a train ticket cost from Kissimmee to Chicago?

The cheapest train tickets from Kissimmee to Chicago start from £143. The average price for this train route is around £255. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.

How long is the train journey from Kissimmee to Chicago?

The average train journey time from Kissimmee to Chicago is 1d 21h, covering a distance of 1000 miles. The fastest train gets you there in 1d 15h and is operated by Amtrak .

Which train operators serve the Kissimmee to Chicago route?

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

What are the earliest and latest departure times for the train from Kissimmee to Chicago?

The earliest train from Kissimmee to Chicago departs at 11:57. And the latest train departs at 18:10.

Train Kissimmee to Chicago from £137 | Refundable Tickets

Next train departures

Next departures from Kissimmee to Chicago on 29 January
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	CheapestFastest
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 23h	10:12	Chicago (Union Station), IL	No tags

Next departures from Kissimmee to Chicago on 30 January
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	CheapestFastest
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 23h	10:12	Chicago (Union Station), IL	No tags

Next departures from Kissimmee to Chicago on 31 January
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	CheapestFastest
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 23h	10:12	Chicago (Union Station), IL	No tags

Next departures from Kissimmee to Chicago on 1 February
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	CheapestFastest
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 23h	10:12	Chicago (Union Station), IL	No tags

Next departures from Kissimmee to Chicago on 3 February
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	CheapestFastest
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 23h	10:12	Chicago (Union Station), IL	No tags

Next departures from Kissimmee to Chicago on 4 February
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	CheapestFastest
Train	18:10	SunRail Station	1d 15h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 21h	08:45	Chicago (Union Station), IL	No tags
Train	11:57	SunRail Station	1d 23h	10:12	Chicago (Union Station), IL	No tags

Last refresh of the prices: Last Saturday at 23:42 EST.

Compare 2 ways to travel 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 £93, 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£93 - £259	Average duration1d 9h	CO₂ emissions 40kg CO₂e
Train	Average price£143 - £1,779	Average duration1d 21h	CO₂ emissions 147kg CO₂e

Train Companies

Amtrak

4/55,752 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wi‑Fi3.6

Based on 5752 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi‑Fi. Amtrak ticket prices on this trip start at £143

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

Frequently asked questions about travelling from Kissimmee to Chicago by train

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

How much does a train ticket cost from Kissimmee to Chicago?
The cheapest train tickets from Kissimmee to Chicago start from £143. The average price for this train route is around £255. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the train journey from Kissimmee to Chicago?
The average train journey time from Kissimmee to Chicago is 1d 21h, covering a distance of 1000 miles. The fastest train gets you there in 1d 15h and is operated by Amtrak.
Which train operators serve the Kissimmee to Chicago route?
Several major train operators run on this route with 3 trains available per day.
What are the earliest and latest departure times for the train from Kissimmee to Chicago?
The earliest train from Kissimmee to Chicago departs at 11:57. And the latest train departs at 18:10.

Find cheapest prices for trains

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

Best price found

27/01

£340

28/01

£244

Today

£168

30/01

£168

31/01

£137

01/02

£168

02/02

No data

03/02

£168

The cheapest trip from Kissimmee to Chicago was searched and found on 31 Jan 2026 with a price of £137

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 £137 to £1,348 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 £137, which is on 2026-01-31.