How much is the bus ticket from Chicago to Kissimmee?

The cheapest bus tickets from Chicago to Kissimmee start at R 2 149. The average price for this route is around R 2 946. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.

How long is the bus journey from Chicago to Kissimmee?

The average bus journey time from Chicago to Kissimmee is 1d 5h, covering a distance of 1592 km. The fastest bus gets you there in 1d 4h and is operated by FlixBus .

Which bus companies service the Chicago to Kissimmee route?

Several major bus companies operate on this route with 9 buses available per day, including services from FlixBus , Greyhound .

What is the earliest and latest departure time for the bus from Chicago to Kissimmee?

The earliest bus departs from Chicago to Kissimmee at 05:25. And the latest bus departs at 23:59.

What are the CO₂ emissions for the bus trip from Chicago to Kissimmee?

A bus trip from Chicago to Kissimmee produces an estimated 40 kg of CO₂, making it a highly eco-friendly travel option and Busbud’s recommended way to travel.

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 reviews on Busbud, the bus company FlixBus has the best Wi-Fi rating with a score of 2.7.

Which bus company offers the most punctual service 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.

Bus Chicago to Kissimmee from R 1 927 | Refundable Tickets

Next bus departures

Next departures from Chicago to Kissimmee on 2 December
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
FlixBus + Greyhound Lines, Inc.	Bus	13:30	Chicago 95Th & Dan Ryan	1d 3h	18:15	E Osceola Pkwy	CheapestFastest
FlixBus + Greyhound Lines, Inc.	Bus	13:00	Downtown Greyhound Station	1d 4h	18:15	E Osceola Pkwy	No tags
Greyhound Lines, Inc. + FlixBus	Bus	21:40	Downtown Greyhound Station	1d 6h	05:05	E Osceola Pkwy	No tags
Greyhound Lines, Inc. + FlixBus	Bus	22:00	537-517 W. Jackson Blvd	1d 6h	05:05	E Osceola Pkwy	No tags
Greyhound Lines, Inc. + FlixBus	Bus	22:30	Chicago 95Th & Dan Ryan	1d 5h	05:05	E Osceola Pkwy	No tags

Next departures from Chicago to Kissimmee on 3 December
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
FlixBus + Greyhound Lines, Inc.	Bus	13:30	Chicago 95Th & Dan Ryan	1d 3h	18:15	E Osceola Pkwy	CheapestFastest
Greyhound Lines, Inc. + FlixBus	Bus	06:10	Downtown Greyhound Station	1d 5h	12:35	E Osceola Pkwy	No tags
	Bus	10:00	537-517 W. Jackson Blvd	1d 7h	18:15	E Osceola Pkwy	No tags
FlixBus + Greyhound Lines, Inc.	Bus	13:00	Downtown Greyhound Station	1d 4h	18:15	E Osceola Pkwy	No tags
Greyhound Lines, Inc. + FlixBus	Bus	21:40	Downtown Greyhound Station	1d 6h	05:05	E Osceola Pkwy	No tags

Next departures from Chicago to Kissimmee on 4 December
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
FlixBus + Greyhound Lines, Inc.	Bus	13:30	Chicago 95Th & Dan Ryan	1d 3h	18:15	E Osceola Pkwy	CheapestFastest
Greyhound Lines, Inc. + FlixBus	Bus	06:10	Downtown Greyhound Station	1d 5h	12:35	E Osceola Pkwy	No tags
	Bus	10:00	537-517 W. Jackson Blvd	1d 7h	18:15	E Osceola Pkwy	No tags
FlixBus + Greyhound Lines, Inc.	Bus	13:00	Downtown Greyhound Station	1d 4h	18:15	E Osceola Pkwy	No tags
Greyhound Lines, Inc. + FlixBus	Bus	21:40	Downtown Greyhound Station	1d 6h	05:05	E Osceola Pkwy	No tags

Next departures from Chicago to Kissimmee on 5 December
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Greyhound Lines, Inc. + FlixBus	Bus	22:30	Chicago 95Th & Dan Ryan	1d 5h	05:05	E Osceola Pkwy	Cheapest
FlixBus + Greyhound Lines, Inc.	Bus	13:30	Chicago 95Th & Dan Ryan	1d 3h	18:15	E Osceola Pkwy	Fastest
Greyhound Lines, Inc. + FlixBus	Bus	06:10	Downtown Greyhound Station	1d 5h	12:35	E Osceola Pkwy	No tags
	Bus	10:00	537-517 W. Jackson Blvd	1d 7h	18:15	E Osceola Pkwy	No tags
FlixBus + Greyhound Lines, Inc.	Bus	13:00	Downtown Greyhound Station	1d 4h	18:15	E Osceola Pkwy	No tags

Last refresh of the prices: Last Sunday at 2:18 AM CST.

Compare 2 ways to travel from Chicago to Kissimmee

We recommend taking the bus

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 R 2 149, it presents an excellent value for a comfortable ride.

9bus per day

1d 5hAverage duration

1592 kmDistance

40kgCO₂ emissions

	Average price	Average duration	CO₂ emissions	Actions
Bus	Average priceR 2 149 - R 8 623	Average duration1d 5h	CO₂ emissions 40kg CO₂e
Train	Average priceR 4 120 - R 52 009	Average duration1d 14h	CO₂ emissions 147kg CO₂e

Where are the popular stops in Chicago and Kissimmee?

Stops in Chicago

A
Downtown Greyhound Station
630 W Harrison St, Chicago, IL 60607, USA
Visit page
B
Chicago O'Hare International Airport
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

FlixBus

3.5/511 498 reviews

Staff4.2

Timeliness3.9

Cleanliness4.1

WiFi2.7

Greyhound

3.5/587 412 reviews

Staff3.6

Timeliness2.9

Cleanliness3.3

WiFi2.4

US Bus Companies: FlixBus, BlaBlaCar Bus, ALSA, Greyhound, Intercape, Trenitalia, Big Sky

Frequently asked questions about travelling from Chicago to Kissimmee by bus

Please note that timetables, routes, or operator details shown here may be updated or differ 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 at R 2 149. The average price for this route is around R 2 946. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the bus journey from Chicago to Kissimmee?
The average bus journey time from Chicago to Kissimmee is 1d 5h, covering a distance of 1592 km. The fastest bus gets you there in 1d 4h and is operated by FlixBus.
Which bus companies service the Chicago to Kissimmee route?
Several major bus companies operate on this route with 9 buses available per day, including services from FlixBus, Greyhound.
What is the earliest and latest departure time for the bus from Chicago to Kissimmee?
The earliest bus departs from Chicago to Kissimmee at 05:25. And the latest bus departs at 23:59.
What are the CO₂ emissions for the bus trip from Chicago to Kissimmee?
A bus trip from Chicago to Kissimmee produces an estimated 40 kg of CO₂, making it a highly eco-friendly travel option and Busbud’s recommended way to travel.
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 reviews on Busbud, the bus company FlixBus has the best Wi-Fi rating with a score of 2.7.
Which bus company offers the most punctual service 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.

Best price found

30/11

R 7 358

01/12

R 6 325

Today

R 3 224

03/12

R 4 275

04/12

R 3 241

05/12

R 2 733

06/12

No data

07/12

No data

The cheapest trip from Chicago to Kissimmee was searched and found on 05 Dec 2025 with a price of R 2 733

To 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 R 2 733 to R 7 358 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 R 2 733, which is on 2025-12-05.