How much does a train ticket from Osceola to Chicago cost?

The average train ticket price from Osceola to Chicago is $76. The best way to find 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 train 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 322 miles 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 have layovers. 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.

What are the best sights and things to do in Chicago?

Once in Chicago, you can explore the city. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.

Train Osceola to Chicago from $46 | Refundable Tickets

Next train departures

Next departures for Osceola to Chicago on November 19
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	7:38am	Osceola Station	14h 13m	9:51pm	Chicago (Union Station), IL	Cheapest
Train	7:38am	Osceola Station	7h 1m	2:39pm	Chicago (Union Station), IL	Fastest
Train	7:38am	Osceola Station	7h 1m	2:39pm	Chicago (Union Station), IL	No tags
Train	7:38am	Osceola Station	14h 13m	9:51pm	Chicago (Union Station), IL	No tags

Next departures for Osceola to Chicago on November 20
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	7:38am	Osceola Station	7h 1m	2:39pm	Chicago (Union Station), IL	CheapestFastest
Train	7:38am	Osceola Station	7h 1m	2:39pm	Chicago (Union Station), IL	No tags
Train	7:38am	Osceola Station	14h 13m	9:51pm	Chicago (Union Station), IL	No tags
Train	7:38am	Osceola Station	14h 13m	9:51pm	Chicago (Union Station), IL	No tags

Next departures for Osceola to Chicago on November 21
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended	Price and booking link
	Train	7:38am	Osceola Station	14h 13m	9:51pm	Chicago (Union Station), IL	Cheapest
	Train	7:38am	Osceola Station	7h 1m	2:39pm	Chicago (Union Station), IL	Fastest

Next departures for Osceola to Chicago on November 22
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended	Price and booking link
	Train	7:38am	Osceola Station	14h 13m	9:51pm	Chicago (Union Station), IL	Cheapest
	Train	7:38am	Osceola Station	7h 1m	2:39pm	Chicago (Union Station), IL	Fastest

Next departures for Osceola to Chicago on November 23
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	7:38am	Osceola Station	14h 13m	9:51pm	Chicago (Union Station), IL	Cheapest
Train	7:38am	Osceola Station	7h 1m	2:39pm	Chicago (Union Station), IL	Fastest
Train	7:38am	Osceola Station	7h 1m	2:39pm	Chicago (Union Station), IL	No tags
Train	7:38am	Osceola Station	14h 13m	9:51pm	Chicago (Union Station), IL	No tags

Next departures for Osceola to Chicago on November 24
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	7:38am	Osceola Station	14h 13m	9:51pm	Chicago (Union Station), IL	Cheapest
Train	7:38am	Osceola Station	7h 1m	2:39pm	Chicago (Union Station), IL	Fastest
Train	7:38am	Osceola Station	7h 1m	2:39pm	Chicago (Union Station), IL	No tags
Train	7:38am	Osceola Station	14h 13m	9:51pm	Chicago (Union Station), IL	No tags

Last refresh of the prices: Today at 3:12 AM CST.

Compare 2 ways to go from Osceola to Chicago

We recommend taking the train

Among the sustainable travel choices, the train stands out as the good way to reach Chicago. The journey takes about 7 hours 1 minute and with fares starting at just $44, it presents an excellent value for a comfortable ride.

2train per day

7h 1mAverage Duration

322 milesDistance

47kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average Price$83 - $168	Average Duration7h 35m	CO₂ emissions 13kg CO₂e
Train	Average Price$44 - $308	Average Duration7h 1m	CO₂ emissions 47kg CO₂e

Train Companies

Amtrak

4/55,593 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5593 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 $44

Amtrak Osceola Chicago recent customer reviews

Very pleasant

Milciades S.

July 27, 2023

Train and bus companies in US:Amtrak, Trenitalia, Renfe, VIA Rail Canada, Amtrak Acela, NS Nederlandse Spoorwegen, Iryo

Frequently asked questions about traveling from Osceola, IA to Chicago by train

How much does a train ticket from Osceola to Chicago cost?
How long is the train trip from Osceola to Chicago?
How many daily trains are there between Osceola and Chicago?
Which train companies travel from Osceola to Chicago?
What are the best sights and things to do in Chicago?

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

11/16

$103

11/17

$119

Today

$54

11/19

$56

11/20

$103

11/21

$279

11/22

$263

11/23

$72

The cheapest trip from Osceola, IA to Chicago was searched and found on Nov 18, 2025 with a price of $54

To 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 $54 to $337 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 $56 which is on 2025-11-19.

What's the cheapest way to go from Osceola, IA to Chicago?

The train is the cheapest travel choice for this destination

Vehicle Type	Travel Time	Avg Price	Daily Departures
Vehicle TypeBus	Travel Time7h 35m	Avg Price$161	Daily Departures1
Vehicle TypeTrain	Travel Time7h 1m	Avg Price$76	Daily Departures2

The 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 $76 on average. If you're on a budget, you'll find cheap tickets from $44. 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!