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 | E Osceola Pkwy | Chicago 95Th & Dan Ryan | Cheapest | ||||
FlixBus + Greyhound Lines, Inc. | Bus | E Osceola Pkwy | Downtown Greyhound Station | Fastest | ||||
 | Bus | E Osceola Pkwy | Downtown Greyhound Station | No tags | ||||
FlixBus + Greyhound Lines, Inc. | Bus | E Osceola Pkwy | Downtown Greyhound Station | No tags | ||||
FlixBus + Greyhound Lines, Inc. | Bus | E Osceola Pkwy | 537-517 W. Jackson Blvd | No tags |
Last refresh of the prices: Last Saturday at 11:42 PM EST.
Compare 2 ways to go from Kissimmee to Chicago
Among the sustainable travel choices, the Bus stands out as a good way to reach Chicago. The journey takes about 1 day, 9 hours 20 minutes, and with fares starting at just $174, it presents an excellent value for a comfortable ride.
Where are the popular stops in Kissimmee and Chicago?
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
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
Compare bus companies
Frequently asked questions about travelling from Kissimmee 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 Kissimmee to Chicago?
The cheapest bus tickets from Kissimmee to Chicago start from $174. The average price for this route is around $235. 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 Kissimmee to Chicago?
The average bus travel time from Kissimmee to Chicago is 1d 9h, covering a distance of 1608 km. The quickest bus can get you there in 1d 3h and is operated by Greyhound.
Which bus companies service the Kissimmee to Chicago route?
What are the earliest and latest departure times for the bus from Kissimmee to Chicago?
The earliest bus departs from Kissimmee to Chicago at 3:35pm. And the latest bus departs at 11:40pm.
What are the CO₂ emissions for the bus trip from Kissimmee to Chicago?
A bus trip from Kissimmee to Chicago 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 Kissimmee to Chicago?
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 12050 reviews.
Which bus company has the best Wi-Fi from Kissimmee to Chicago?
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 Kissimmee to Chicago?
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 Kissimmee to Chicago?
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 Kissimmee to Chicago was searched and found on Feb 1, 2026 with a price of $181To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Kissimmee to Chicago, as early as possible.
You can expect to pay from $181 to $386 for a bus ticket from Kissimmee to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $181 which is on 2026-02-01.
What's the cheapest way to go from Kissimmee to Chicago?
The Bus is the cheapest travel choice for this destination
