Next departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Chicago (Union Station), IL | Winter Park Resort | Cheapest | |||||
| Chicago (Union Station), IL | Fraser Park / Winter Park Station | Fastest | |||||
| Chicago (Union Station), IL | Winter Park Resort | No tags | |||||
| Chicago (Union Station), IL | Fraser Park / Winter Park Station | No tags | |||||
| Chicago (Union Station), IL | Fraser Park / Winter Park Station | No tags |
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Get from Chicago to Winter Park
This route is served by train onlyThe journey takes about 21 hours 48 minutes and with fares starting at just $93, it presents an excellent value for a comfortable ride.
Train Chicago to Winter Park, CO: Trip Overview
Please note, this information is subject to change.
Train Companies
Based on 5549 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
Chicago to Winter Park Train
With Busbud, comparing and booking tickets for a train from Chicago to Winter Park is a breeze. Browse through an extensive selection of train fares and train schedules to find the best deals.
We make it our job to connect you with the most dependable companies that offer train service from Chicago to Winter Park.
From train tickets to high-end trains trip from Chicago to Winter Park, we offer a wide range of train services to best suit your needs depending on how much your budget is.
Frequently asked questions for your trip Chicago - Winter Park, CO
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 Oct 31, 2025 with a price of $157To 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 $157 to $847 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 $157 which is on 2025-10-31.
About Train Travel
Train Travel Tips
Taking the fastest trains allows you to travel at speeds greater than 300 km/h. Taking a trip from Chicago to Winter Park is not only much quicker but more comfortable too! You can usually travel directly to the city centre and save time while you're at it.
Whether you take a regional or high-speed train to Winter Park, you’ll help reduce the environmental impact and carbon footprint of your trip. As you watch the landscapes unfold before your eyes, you can tell yourself that with this choice, you are making sure they remain protected.
The train emits up to 30x less CO2 for a trip between Chicago and Winter Park compared to the same trip made by plane or car. A truly ecological mode of transport that will allow you to easily reduce your carbon footprint.
Tune out to the fine sounds of your best music playlist on your train trip from Chicago to Winter Park while indulging in miles on end of beautiful scenic views.
Did you know?
New York holds the record for the most platforms and track numbers in a single station. Grand Central Station in Manhattan is one of the largest rail terminals in the world with more than 44 platforms and 67 tracks to accommodate passengers.
One of the deepest train stations in the world is in Kiev. Located at a depth of 105 m, it was designed in this way to serve as a shelter in the event of an attack. The second deepest station is in China. Badaling station is located 60 m under the Great Wall of China!
You can find the straightest railway in the world in Australia. This railway line is 478 kilometres long and is also considered the longest and straightest railway line in the world.
Top Traveled Train Routes
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