Next train departures
| 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 | CheapestFastest | ||||
| 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 |
Last refresh of the prices: Today at 11:09 AM CST.
Get from Chicago to Winter Park
The journey takes about 21 hours 48 minutes, and with fares starting at just $159, it presents an excellent value for a comfortable ride.
Train companies
Based on 5759 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi‑Fi. Amtrak ticket prices on this trip start at $159
Frequently asked questions about travelling 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 at $159. The average price for this train route is around $278. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.
How long is the train ride from Chicago to Winter Park?
The average train trip from Chicago to Winter Park takes 21h 48m and covers 1540 km. The quickest train gets you there in 21h 48m and is operated by Amtrak.
Which train operators serve the Chicago to Winter Park route?
Several major train operators serve this route, with 1 trains available per day.
What are the earliest and latest departure times for the train from Chicago to Winter Park?
The earliest train from Chicago to Winter Park departs at 7:40am. 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 Feb 17, 2026 with a price of $267To 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 $267 to $911 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 $267 which is on 2026-02-20.
