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 | Osceola Station | No tags | ||||
| Train | Chicago (Union Station), IL | Osceola Station | No tags | ||||
| Train | Chicago (Union Station), IL | Osceola Station | No tags | ||||
| Train | Chicago (Union Station), IL | Osceola Station | No tags | ||||
| Train | Chicago (Union Station), IL | Osceola Station | No tags |
Compare 2 ways to go from Chicago to Osceola
Among the sustainable travel choices, the train stands out as the good way to reach Osceola. The journey takes about 6 hours 23 minutes and with fares starting at just $49, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5638 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 $49
Frequently asked questions about traveling from Chicago to Osceola, IA 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 Osceola?
The cheapest train tickets from Chicago to Osceola start from $49. The average price for this train route is around $90. 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 Osceola?
The average train ride duration from Chicago to Osceola is 6h 23m, covering a distance of 322 miles (519 km). The quickest train can get you there in 6h 23m and is operated by Amtrak.
Which train operators service the Chicago to Osceola route?
Several major train operators operate on this route with 2 trains available per day.
What is the earliest and latest departure time for the train from Chicago to Osceola?
The earliest train departs from Chicago to Osceola 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 Osceola, IA was searched and found on Dec 10, 2025 with a price of $50To 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 $50 to $337 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 $50 which is on 2025-12-12.
