Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Chicago (Union Station), IL | Fraser Park / Winter Park Station | No tags | ||||
| Train | Chicago (Union Station), IL | Fraser Park / Winter Park Station | No tags | ||||
| Train | Chicago (Union Station), IL | Fraser Park / Winter Park Station | No tags | ||||
| Train | Chicago (Union Station), IL | Fraser Park / Winter Park Station | No tags | ||||
| Train | Chicago (Union Station), IL | Fraser Park / Winter Park Station | No tags |
Get from Chicago to Winter Park
The journey takes about 21 hours 48 minutes and with fares starting at just $93, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5639 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
Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.
How much is the train ticket from Chicago to Winter Park?
The cheapest train tickets from Chicago to Winter Park start from $93. The average price for this train route is around $230. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the train journey from Chicago to Winter Park?
The average train ride duration from Chicago to Winter Park is 21h 48m, covering a distance of 955 miles (1540 km). The quickest train can get you there in 21h 48m and is operated by Amtrak.
Which train operators service the Chicago to Winter Park route?
Several major train operators operate on this route with 1 trains available per day.
What is the earliest and latest departure time for the train from Chicago to Winter Park?
The earliest train departs from Chicago to Winter Park at 7:40am. And the latest train departs at 2:00pm.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Chicago to Winter Park, CO was searched and found on Dec 13, 2025 with a price of $128To 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 $128 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 $128 which is on 2025-12-13.
