Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
FlixBus + Greyhound Lines, Inc. | Bus | Chicago 95Th & Dan Ryan | E Osceola Pkwy | CheapestFastest | ||||
Greyhound Lines, Inc. + FlixBus | Bus | Downtown Greyhound Station | E Osceola Pkwy | No tags | ||||
 | Bus | 537-517 W. Jackson Blvd | E Osceola Pkwy | No tags | ||||
FlixBus + Greyhound Lines, Inc. | Bus | Downtown Greyhound Station | E Osceola Pkwy | No tags | ||||
Greyhound Lines, Inc. + FlixBus | Bus | Downtown Greyhound Station | E Osceola Pkwy | No tags |
Last refresh of the prices: Last Sunday at 2:18 AM CST.
Compare 2 ways to go from Chicago to Kissimmee
Among the sustainable travel choices, the bus stands out as a good way to reach Kissimmee. The journey takes about 1 day, 5 hours 35 minutes, and with fares starting at just $177, it presents an excellent value for a comfortable ride.
Where are the popular stops in Chicago and Kissimmee?
Stops in Chicago
- A630 W Harrison St, Chicago, IL 60607, USA
- C
Polk St & Canal St
500-536 W Polk St, Chicago IL 60607, USA - D
Tornado Bus S Kedzie Ave
2807 S Kedzie Ave, Chicago, IL 60623, USA - E
Cumberland CTA
5800 N Cumberland Ave, Chicago, IL 60631, USA - F
Turimex California Ave
2139 S California Ave, Chicago, IL 60608, USA
Stops in Kissimmee
- A
E Osceola Pkwy
1471 East Osceola Pkwy (Walmart), Kissimmee, FL 34744-1604 - B
Kissimmee Station
103 E Dakin Ave, Kissimmee, FL 34741 - C
Denny's
5855 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34746 - D
Irlo Bronson Memorial Hwy McDonald's
5725 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34746, USA - E
Davenport Days Inn
2425 Frontage Rd , Davenport , 33837
Compare bus companies
Frequently asked questions about travelling from Chicago to Kissimmee 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 Chicago to Kissimmee?
The cheapest bus tickets from Chicago to Kissimmee start from $177. The average price for this route is around $242. 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 Chicago to Kissimmee?
The average bus travel time from Chicago to Kissimmee is 1d 5h, covering a distance of 1592 km. The quickest bus can get you there in 1d 4h and is operated by FlixBus.
Which bus companies service the Chicago to Kissimmee route?
What are the earliest and latest departure times for the bus from Chicago to Kissimmee?
The earliest bus departs from Chicago to Kissimmee at 5:25am. And the latest bus departs at 11:59pm.
What are the CO₂ emissions for the bus trip from Chicago to Kissimmee?
A bus trip from Chicago to Kissimmee generates an estimated 40 kg of CO₂, making it a highly eco-friendly travel option and a mode of travel recommended by Busbud.
What is the best bus company from Chicago to Kissimmee?
According to Busbud customers, the highest-rated bus company on this route is FlixBus, with an average rating of 3.5 out of 5 stars based on 11380 reviews.
Which bus company has the best Wi-Fi from Chicago to Kissimmee?
Based on Busbud reviews, the bus company FlixBus has the highest Wi-Fi rating with a score of 2.7.
Which bus company has the best on-time performance from Chicago to Kissimmee?
According to Busbud traveller reviews, the most punctual bus company on this route is FlixBus, with a punctuality rating of 3.9 out of 5 stars.
Which bus company has the cleanest buses from Chicago to Kissimmee?
According to Busbud traveller reviews, the bus company with the cleanest buses on this route is FlixBus, with a cleanliness rating of 4.1 out of 5 stars.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Chicago to Kissimmee was searched and found on Dec 5, 2025 with a price of $225To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Chicago to Kissimmee, as early as possible.
You can expect to pay from $225 to $604 for a bus ticket from Chicago to Kissimmee based on the last 2 days. You can expect to find the cheapest price for the trip at $225 which is on 2025-12-05.
What's the cheapest way to go from Chicago to Kissimmee?
The bus is the cheapest travel choice for this destination
