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 a good way to reach Osceola. The journey takes about 6 hours 23 minutes, and with fares starting at just $62, it presents an excellent value for a comfortable ride.
Train companies
Based on 5750 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 $62
Frequently asked questions about travelling 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 at $62. The average price for this train route is around $107. 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 Osceola?
The average train trip from Chicago to Osceola takes 6h 23m and covers 519 km. The quickest train gets you there in 6h 23m and is operated by Amtrak.
Which train operators serve the Chicago to Osceola 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 Osceola?
The earliest train from Chicago to Osceola 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 Osceola, IA was searched and found on Jan 28, 2026 with a price of $65To 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 $65 to $368 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 $65 which is on 2026-01-28.
What's the cheapest way to go from Chicago to Osceola, IA?
The Train is the cheapest travel choice for this destinationThe best way to travel between Chicago and Osceola, IA is by train. By choosing the train, you'll get to save some money as you travel to your destination, as ticket prices cost $107 on average. If you're on a budget, you'll find cheap tickets from $62. If you're looking for the fastest way to get to Osceola, IA, choose the train, as it will take you from Chicago to Osceola, IA in about 6h 23m —that's the fastest way to get there!
