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
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?
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.
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.