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Chicago Union Station to Kissimmee trains

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Trip Overview

The train between Chicago Union Station and Kissimmee takes 38h 58m. There is at least one train per day from Chicago Union Station to Kissimmee. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

38h 58m
Duration
1,721 mi
Distance
$1,100
Average price
Once daily
Frequency

Chicago Union Station to Kissimmee train times

Trains run once daily between Chicago Union Station and Kissimmee. The service departs Chicago Union Station at 6:40 PM in the evening, which arrives into Kissimmee at 10:38:00. All services run direct with no transfers required, and take on average 38h 58m. The schedules shown below are for the next available departures.

Departing Wednesday, November 11, 2026

  •  → 

    Arrives +2 days

    train train 38h 58m • Direct

Departing Thursday, November 12, 2026

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    Arrives +2 days

    train train 38h 58m • Direct

Departing Friday, November 13, 2026

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    Arrives +2 days

    train train 38h 58m • Direct

Departing Saturday, November 14, 2026

  •  → 

    Arrives +2 days

    train train 38h 58m • Direct

Departing Sunday, November 15, 2026

  •  → 

    Arrives +2 days

    train train 38h 58m • Direct

Departing Monday, November 16, 2026

  •  → 

    Arrives +2 days

    train train 38h 58m • Direct

Departing Tuesday, November 17, 2026

  •  → 

    Arrives +2 days

    train train 38h 58m • Direct

Frequently asked questions

Want to know about travelling from Chicago Union Station to Kissimmee? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.

Map of how to get from Chicago Union Station to Kissimmee.ExpandLaunch map view
  • Distance: 1,720.8 mi
  • Duration: 38h 58m

What companies run services between Chicago Union Station, IL, USA and Kissimmee, FL, USA?

Amtrak operates a train from Chicago Union Station to Kissimmee Amtrak Station once daily. Tickets cost $950–1,500 and the journey takes 38h 58m.

Operators