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 |
Last refresh of the prices: Today at 8:10 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 $64, it presents an excellent value for a comfortable ride.
Train companies
Based on 5607 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 $64
Amtrak Osceola Chicago recent customer reviews
Very pleasant
Milciades S.
Frequently asked questions about travelling from Osceola, IA to Chicago by train
How much does a cheap train ticket from Osceola to Chicago cost?
The average train ticket price from Osceola to Chicago is $108. The best way to find cheap train tickets from Osceola to Chicago 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 trip from Osceola to Chicago?
A train trip between Osceola and Chicago is around 7h 1m, although the fastest train will take about 7h 1m. This is the time it takes to travel the 519 km that separates the two cities.
How many daily trains are there between Osceola and Chicago?
The number of trains from Osceola to Chicago 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 Osceola to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Osceola to Chicago?
When taking the train from Osceola to Chicago, 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 Osceola, IA to Chicago was searched and found on Nov 23, 2025 with a price of $116To 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 $116 to $488 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 $123 which is on 2025-11-28.
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 $108 on average. If you're on a budget, you'll find cheap tickets from $64. 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!
