Next train departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Osceola Station | Chicago (Union Station), IL | Cheapest | ||||
| Train | Osceola Station | Chicago (Union Station), IL | Fastest | ||||
| Train | Osceola Station | Chicago (Union Station), IL | No tags | ||||
| Train | Osceola Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Today at 6:55 AM CST.
Compare 2 ways to go from Osceola to Chicago
Among the sustainable travel choices, the train stands out as a good way to reach Chicago. The journey takes about 7 hours 1 minute, and with fares starting at just $62, it presents an excellent value for a comfortable ride.
Train companies
Based on 5639 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 WiFi. Amtrak ticket prices on this trip start at $62
Amtrak Osceola Chicago recent customer reviews
Very pleasant
Milciades S.
Frequently asked questions about travelling from Osceola, IA to Chicago 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 Osceola to Chicago?
The cheapest train tickets from Osceola to Chicago start at $62. The average price for this train route is around $106. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.
How long is the train ride from Osceola to Chicago?
The average train trip from Osceola to Chicago takes 7h 1m and covers 519 km. The quickest train gets you there in 7h 1m and is operated by Amtrak.
Which train operators serve the Osceola to Chicago route?
Several major train operators serve this route, with 2 trains available per day.
What are the earliest and latest departure times for the train from Osceola to Chicago?
The earliest train from Osceola to Chicago departs at 7:38am. The latest train departs at 7:38am.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Osceola, IA to Chicago was searched and found on Dec 10, 2025 with a price of $71To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Osceola, IA to Chicago, as early as possible.
You can expect to pay from $71 to $476 for a train ticket from Osceola, IA to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $71 which is on 2025-12-15.
What's the cheapest way to go from Osceola, IA to Chicago?
The train is the cheapest travel choice for this destinationThe best way to travel between Osceola, IA and Chicago is by train. By choosing the train, you'll get to save some money as you travel to your destination, as ticket prices cost $106 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 Chicago, choose the train, as it will take you from Osceola, IA to Chicago in about 7h 1m —that's the fastest way to get there!
