How much does a train ticket from Chicago to Winter Park cost?

The average train ticket price from Chicago to Winter Park is $198. The best way to find train tickets from Chicago to Winter Park 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 Winter Park?

A train trip between Chicago and Winter Park is around 22h 48m, although the fastest train will take about 21h 48m. This is the time it takes to travel the 954 miles that separates the two cities.

How many daily trains are there between Chicago and Winter Park?

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

Which train companies travel from Chicago to Winter Park?

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

Train Chicago to Winter Park from $88 | Refundable Tickets

Next departures

Next departures for Chicago to Winter Park on November 30
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended	Price and booking link
		2:00pm	Chicago (Union Station), IL	22h 11m	11:11am	Winter Park Resort	Cheapest
		2:00pm	Chicago (Union Station), IL	21h 48m	10:48am	Fraser Park / Winter Park Station	Fastest

Last refresh of the prices: Today at 11:51 AM CST.

Get from Chicago to Winter Park

This route is served by train only

The journey takes about 22 hours 48 minutes and with fares starting at just $93, it presents an excellent value for a comfortable ride.

2train per day

22h 48mAverage Duration

955 milesDistance

140kgCO₂ emissions

Train Companies

Amtrak

4/55,614 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5614 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 $93

Train and bus companies in US:Amtrak, Trenitalia, Renfe, VIA Rail Canada, Amtrak Acela, NS Nederlandse Spoorwegen, Iryo

Frequently asked questions about traveling from Chicago to Winter Park, CO by train

How much does a train ticket from Chicago to Winter Park cost?
How long is the train trip from Chicago to Winter Park?
How many daily trains are there between Chicago and Winter Park?
Which train companies travel from Chicago to Winter Park?

Find cheapest prices for trains

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

Best price found

11/27

$228

11/28

$337

Today

$337

11/30

$739

12/01

No data

12/02

No data

12/03

No data

12/04

No data

The cheapest trip from Chicago to Winter Park, CO was searched and found on Nov 27, 2025 with a price of $228

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

You can expect to pay from $228 to $739 for a train ticket from Chicago to Winter Park, CO based on the last 2 days. You can expect to find the cheapest price for the trip at $739 which is on 2025-11-30.