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 | Osceola Station | Cheapest | ||||
| Train | Chicago (Union Station), IL | Osceola Station | Fastest | ||||
| Train | Chicago (Union Station), IL | Osceola Station | No tags | ||||
| Train | Chicago (Union Station), IL | Osceola Station | No tags |
Last refresh of the prices: Yesterday at 17:52 CST.
Compare 2 ways to travel from Chicago to Osceola
Among the sustainable travel choices, the train stands out as a good way to reach Osceola. The journey takes about 6 hours 23 minutes and with fares starting at just £35, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5594 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 £35
Frequently asked questions about travelling from Chicago to Osceola, IA by train
How much does a cheap train ticket from Chicago to Osceola cost?
The average train ticket price from Chicago to Osceola is £67. The best way to find cheap train tickets from Chicago to Osceola 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 Osceola?
A train trip between Chicago and Osceola is around 6h 23m, although the fastest train will take about 6h 23m. This is the time it takes to travel the 322 miles that separates the two cities.
How many daily train are there between Chicago and Osceola?
The number of trains from Chicago to Osceola can differ depending on the day of the week. On average, there are 2. Some trains are direct while others include transferring trains. Simplify your train trip from Chicago to Osceola by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Chicago to Osceola?
When taking the train from Chicago to Osceola, 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.
The cheapest trip from Chicago to Osceola, IA was searched and found on 19 Nov 2025 with a price of £48To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Chicago to Osceola, IA as early as possible.
You can expect to pay from £48 to £352 for a train ticket from Chicago to Osceola, IA based on the last 2 days. You can expect to find the cheapest price for the trip at £52, which is on 2025-11-21.
