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Milwaukee to Winter Park trains

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Trip Overview

The train between Milwaukee and Winter Park takes 41h 39m. There is at least one train per day from Milwaukee to Winter Park. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

41h 39m
Duration
1,783 mi
Distance
$1,155
Average price
Once daily
Frequency

Milwaukee to Winter Park train times

Trains run once daily between Milwaukee and Winter Park. The service departs Milwaukee at 3:00 PM in the afternoon, which arrives into Winter Park at 08:39:00. All services require a transfer, and take on average 41h 39m. The schedules shown below are for the next available departures.

Departing Friday, October 30, 2026

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    Arrives +2 days

    AmtrakAmtrak41h 39m • 1 change

Departing Saturday, October 31, 2026

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    Arrives +2 days

    AmtrakAmtrak41h 39m • 1 change

Departing Sunday, November 1, 2026

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    Arrives +2 days

    AmtrakAmtrak41h 39m • 1 change

Departing Monday, November 2, 2026

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    Arrives +2 days

    AmtrakAmtrak41h 39m • 1 change

Departing Tuesday, November 3, 2026

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    Arrives +2 days

    AmtrakAmtrak41h 39m • 1 change

Departing Wednesday, November 4, 2026

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    Arrives +2 days

    AmtrakAmtrak41h 39m • 1 change

Departing Thursday, November 5, 2026

  •  → 

    Arrives +2 days

    AmtrakAmtrak41h 39m • 1 change

Frequently asked questions

Want to know about travelling from Milwaukee to Winter Park? 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 Milwaukee to Winter Park.ExpandLaunch map view
  • Distance: 1,783.1 mi
  • Duration: 41h 39m

What companies run services between Milwaukee, WI, USA and Winter Park, FL, USA?

You can take a train from Milwaukee to Winter Park Amtrak Station via Chicago Union Station in around 40h 28m.

Operators