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Cheap bus tickets from Chicago to Osceola

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Chicago to Osceola Bus Schedule

No preview is currently available. Please try another date or search the full schedule.

Bus from Chicago to Osceola: Journey Information

There is one daily bus from Chicago to Osceola. Traveling by bus from Chicago to Osceola usually takes around 13 hours and 26 minutes, but the fastest Jefferson Lines bus can make the trip in 13 hours and 25 minutes.

Distance416 mi (670 km)
Shortest duration13h 25m
Cheapest price$168.00
Most frequent serviceJefferson Lines
Bus lines1

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What bus companies travel from Chicago to Osceola?

There is one intercity bus company available to search and book on Wanderu that operates from Chicago to Osceola. Jefferson Lines is the only company that has bus schedules available to search and book at the moment. It only makes the trip once a day on most days.

BusDaily TripsAvg. TimeAvg. Price
Jefferson Lines113h 26m$168.00
  • Book Jefferson Lines from Chicago to Osceola from $168. Typically there is one Jefferson Lines schedule per day from Chicago to Osceola and you can expect on average to pay for a Jefferson Lines ticket to Osceola. In Chicago, Jefferson Lines departs to Osceola from Bus Station - 630 W Harrison St . In Osceola, Jefferson Lines arrives at Joe’s Countryside Market .

    An average trip on Jefferson Lines from Chicago to Osceola takes 13 hours and 26 minutes , while the fastest available Jefferson Lines trip will get you to Osceola in 13 hours and 25 minutes .

Frequently asked questions about traveling by bus from Chicago to Osceola

The bus takes an average of 13 hours and 26 minutes to cover the 416 miles from Chicago to Osceola. However, the fastest bus only takes 13 hours and 25 minutes. It’s definitely on the longer side, so plan to get comfortable for a long road trip. Keep in mind that your actual bus may arrive earlier or later than scheduled, depending on whether there is more or less traffic than usual.

Friday is the busiest travel day for buses as people head from Chicago to Osceola for the weekend. If you are planning to travel on a Friday, you should make sure to book tickets well in advance as they may sell out.

On the other hand, Wednesday is typically the least busy day for bus travel on this route. If you're looking for some extra space on the bus, traveling mid-week is your best bet.

There is usually only one bus per day from Chicago to Osceola. It leaves the station in Chicago at 9:00pm each day. The time might vary for specific dates, so be sure to search on Wanderu for the most up-to-date information.

There is usually only one bus per day from Chicago to Osceola. However, it is not a direct bus, so you will have to get off your original vehicle to change buses during the trip.

City Information

Chicago

Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials and a top destination in Illinois.

You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.

Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.

Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.

Station Information

Where does the bus leave from in Chicago?

Chicago Greyhound Bus Station - CHIGLI3-0

Image credit: Jeramey Jannene

Link to image attribution

Main departure station: Bus Station - 630 W Harrison St

Most buses depart from the main station in Chicago.

All bus stations in Chicago:

  • Bus Station - 630 W Harrison St

Where does the bus arrive in Osceola?

Main arrival station: Joe’s Countryside Market

All buses from Chicago arrive at one main station in Osceola.

All bus stations in Osceola:

  • Joe’s Countryside Market

Get around town with Moovit

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Need a return trip from Osceola to Chicago?

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