Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Bus | W Clay St | Chicago (Bus Station) | No tags | ||||
| Bus | W Clay St | Chicago (Bus Station) | No tags | ||||
| Bus | W Clay St | Chicago (Bus Station) | No tags | ||||
| Bus | W Clay St | Chicago (Bus Station) | No tags | ||||
| Bus | W Clay St | Chicago (Bus Station) | No tags |
Compare 2 ways to go from Osceola to Chicago
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.
Compare bus companies
Founded in 1919, Jefferson Lines provides bus services across the Midwest in the US. Their buses have WiFi, USB plugs, bathrooms, reclining seats, reading lights and GPS tracking. Tickets are non-refundable, but you can change the date by paying a fee. Known for their affordable prices and convenient schedules, if you're looking to travel in the Midwest, Jefferson Lines is the way to go.
Frequently asked questions about traveling from Osceola, IA to Chicago by bus
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 bus ticket from Osceola to Chicago?
The cheapest bus tickets from Osceola to Chicago start from $83. The average price for this route is around $161. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the bus ride from Osceola to Chicago?
The average bus trip duration from Osceola to Chicago is 7h 15m, covering a distance of 323 miles (521 km). The quickest bus can get you there in 7h 15m and is operated by Jefferson Lines.
Which bus companies service the Osceola to Chicago route?
Several major train operators operate on this route with 1 trains available per day.
What is the earliest and latest departure time for the bus from Osceola to Chicago?
The earliest bus departs from Osceola to Chicago at 10:30pm. And the latest bus departs at 10:30pm.
What are the CO₂ emissions for the bus trip from Osceola to Chicago?
A bus trip from Osceola to Chicago generates an estimated 13 kg of CO₂, making it a highly eco-friendly travel option and recommended mode of travel by Busbud.
Find cheapest prices for buses
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 19, 2025 with a price of $156To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Osceola, IA to Chicago, as early as possible.
