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

The average train ticket price from Chicago to Kissimmee is R 7 765. The best way to find cheap train tickets from Chicago to Kissimmee is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!

How long is the train trip from Chicago to Kissimmee?

A train trip between Chicago and Kissimmee is around 1d 14h, although the fastest train will take about 1d 14h. This is the time it takes to travel the 1611 km that separates the two cities.

How many daily train are there between Chicago and Kissimmee?

The number of trains from Chicago to Kissimmee can differ depending on the day of the week. On average, there are 2. Some trains are direct while others include transferring trains. Simplify your train trip from Chicago to Kissimmee by comparing and selecting the train that fits your travel style and budget on Busbud.

Which train companies travel from Chicago to Kissimmee?

When taking the train from Chicago to Kissimmee, you can travel comfortably and safely with Amtrak.

Train Chicago to Kissimmee from R 2 225 | Refundable Tickets

Next departures

Next departures from Chicago to Kissimmee on 2 December
Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
18:40	Chicago (Union Station), IL	1d 14h	10:38	SunRail Station	CheapestFastest
18:40	Chicago (Union Station), IL	1d 14h	10:38	SunRail Station	No tags
18:40	Chicago (Union Station), IL	1d 17h	13:38	SunRail Station	No tags
18:40	Chicago (Union Station), IL	1d 17h	13:38	SunRail Station	No tags

Next departures from Chicago to Kissimmee on 3 December
Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
18:40	Chicago (Union Station), IL	1d 14h	10:38	SunRail Station	CheapestFastest
18:40	Chicago (Union Station), IL	1d 14h	10:38	SunRail Station	No tags
18:40	Chicago (Union Station), IL	1d 17h	13:38	SunRail Station	No tags
18:40	Chicago (Union Station), IL	1d 17h	13:38	SunRail Station	No tags

Next departures from Chicago to Kissimmee on 4 December
Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
18:40	Chicago (Union Station), IL	1d 14h	10:38	SunRail Station	CheapestFastest
18:40	Chicago (Union Station), IL	1d 14h	10:38	SunRail Station	No tags
18:40	Chicago (Union Station), IL	1d 17h	13:38	SunRail Station	No tags
18:40	Chicago (Union Station), IL	1d 17h	13:38	SunRail Station	No tags
17:55	Chicago (Union Station), IL	1d 18h	13:38	SunRail Station	No tags

Next departures from Chicago to Kissimmee on 5 December
Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
18:40	Chicago (Union Station), IL	1d 14h	10:38	SunRail Station	CheapestFastest
18:40	Chicago (Union Station), IL	1d 14h	10:38	SunRail Station	No tags
18:40	Chicago (Union Station), IL	1d 17h	13:38	SunRail Station	No tags
18:40	Chicago (Union Station), IL	1d 17h	13:38	SunRail Station	No tags

Last refresh of the prices: Last Sunday at 2:18 AM CST.

Compare 2 ways to travel from Chicago to Kissimmee

We recommend taking the bus

Among the sustainable travel choices, the bus stands out as a good way to reach Kissimmee. The journey takes about 1 day, 5 hours 35 minutes and with fares starting at just R 2 149, it presents an excellent value for a comfortable ride.

9bus per day

1d 5hAverage duration

1592 kmDistance

40kgCO₂ emissions

	Average price	Average duration	CO₂ emissions	Actions
Bus	Average priceR 2 149 - R 8 623	Average duration1d 5h	CO₂ emissions 40kg CO₂e
Train	Average priceR 4 120 - R 52 009	Average duration1d 14h	CO₂ emissions 147kg CO₂e

Train Companies

Amtrak

4/55 620 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

WiFi3.6

Based on 5620 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 R 4 120

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

Frequently asked questions about travelling from Chicago to Kissimmee by train

How much does a cheap train ticket from Chicago to Kissimmee cost?
The average train ticket price from Chicago to Kissimmee is R 7 765. The best way to find cheap train tickets from Chicago to Kissimmee is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the train trip from Chicago to Kissimmee?
A train trip between Chicago and Kissimmee is around 1d 14h, although the fastest train will take about 1d 14h. This is the time it takes to travel the 1611 km that separates the two cities.
How many daily train are there between Chicago and Kissimmee?
The number of trains from Chicago to Kissimmee can differ depending on the day of the week. On average, there are 2. Some trains are direct while others include transferring trains. Simplify your train trip from Chicago to Kissimmee by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Chicago to Kissimmee?
When taking the train from Chicago to Kissimmee, you can travel comfortably and safely with Amtrak.

Find cheapest prices for trains

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

Best price found

30/11

R 8 830

01/12

R 8 130

Today

R 4 731

03/12

R 4 731

04/12

R 4 731

05/12

R 3 960

06/12

No data

07/12

No data

The cheapest trip from Chicago to Kissimmee was searched and found on 05 Dec 2025 with a price of R 3 960

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

You can expect to pay from R 3 960 to R 31 991 for a train ticket from Chicago to Kissimmee based on the last 2 days. You can expect to find the cheapest price for the trip at R 3 960, which is on 2025-12-05.