How much is the bus ticket from Kissimmee to Chicago?

The cheapest bus tickets from Kissimmee to Chicago start from $125. The average price for this route is around $169. 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 trip duration from Kissimmee to Chicago is 1d 9h, covering a distance of 997 miles (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?

Several major bus companies operate on this route with 7 buses available per day, including services from FlixBus , Greyhound .

What is the earliest and latest departure time 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 recommended mode of travel 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 reviews on Busbud, the bus company FlixBus has the best Wi-Fi rating with a score of 2.7.

Which bus company has the most timely service from Kissimmee to Chicago?

According to Busbud traveler reviews, the most timely 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 traveler 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 Kissimmee to Chicago from $130 | Refundable Tickets

Next bus departures

Next departures for Kissimmee to Chicago on January 29
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Greyhound Lines, Inc. + FlixBus	Bus	6:20pm	E Osceola Pkwy	1d 15h	8:25am	Downtown Greyhound Station	Cheapest
	Bus	5:20pm	E Osceola Pkwy	1d 7h	12:10am	Downtown Greyhound Station	Fastest
Greyhound Lines, Inc. + FlixBus	Bus	6:20pm	E Osceola Pkwy	1d 14h	8:00am	537-517 W. Jackson Blvd	No tags
Greyhound Lines, Inc. + FlixBus	Bus	6:20pm	E Osceola Pkwy	1d 16h	9:50am	Chicago 95Th & Dan Ryan	No tags

Next departures for Kissimmee to Chicago on January 30
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
FlixBus + Greyhound Lines, Inc.	Bus	11:40pm	E Osceola Pkwy	1d 11h	9:50am	Chicago 95Th & Dan Ryan	Cheapest
FlixBus + Greyhound Lines, Inc.	Bus	3:35pm	E Osceola Pkwy	1d 5h	8:10pm	Downtown Greyhound Station	Fastest
	Bus	5:20pm	E Osceola Pkwy	1d 7h	12:10am	Downtown Greyhound Station	No tags
FlixBus + Greyhound Lines, Inc.	Bus	11:40pm	E Osceola Pkwy	1d 9h	8:25am	Downtown Greyhound Station	No tags
FlixBus + Greyhound Lines, Inc.	Bus	11:40pm	E Osceola Pkwy	1d 9h	8:00am	537-517 W. Jackson Blvd	No tags

Next departures for Kissimmee to Chicago on January 31
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
FlixBus + Greyhound Lines, Inc.	Bus	3:35pm	E Osceola Pkwy	1d 9h	11:35pm	Chicago 95Th & Dan Ryan	Cheapest
FlixBus + Greyhound Lines, Inc.	Bus	3:35pm	E Osceola Pkwy	1d 5h	8:10pm	Downtown Greyhound Station	Fastest
	Bus	5:20pm	E Osceola Pkwy	1d 7h	12:10am	Downtown Greyhound Station	No tags
FlixBus + Greyhound Lines, Inc.	Bus	11:40pm	E Osceola Pkwy	1d 9h	8:25am	Downtown Greyhound Station	No tags
FlixBus + Greyhound Lines, Inc.	Bus	11:40pm	E Osceola Pkwy	1d 9h	8:00am	537-517 W. Jackson Blvd	No tags

Next departures for Kissimmee to Chicago on February 1
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
	Bus	5:20pm	E Osceola Pkwy	1d 7h	12:10am	Downtown Greyhound Station	Cheapest
FlixBus + Greyhound Lines, Inc.	Bus	3:35pm	E Osceola Pkwy	1d 5h	8:10pm	Downtown Greyhound Station	Fastest
FlixBus + Greyhound Lines, Inc.	Bus	11:40pm	E Osceola Pkwy	1d 9h	8:25am	Downtown Greyhound Station	No tags
FlixBus + Greyhound Lines, Inc.	Bus	11:40pm	E Osceola Pkwy	1d 9h	8:00am	537-517 W. Jackson Blvd	No tags
FlixBus + Greyhound Lines, Inc.	Bus	3:35pm	E Osceola Pkwy	1d 9h	11:35pm	Chicago 95Th & Dan Ryan	No tags

Next departures for Kissimmee to Chicago on February 3
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Greyhound Lines, Inc. + FlixBus	Bus	6:20pm	E Osceola Pkwy	1d 18h	11:30am	Downtown Greyhound Station	CheapestFastest
Greyhound Lines, Inc. + FlixBus	Bus	6:20pm	E Osceola Pkwy	1d 20h	2:10pm	537-517 W. Jackson Blvd	No tags
Greyhound Lines, Inc. + FlixBus	Bus	6:20pm	E Osceola Pkwy	1d 20h	1:25pm	Chicago 95Th & Dan Ryan	No tags

Next departures for Kissimmee to Chicago on February 4
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Greyhound Lines, Inc. + FlixBus	Bus	6:20pm	E Osceola Pkwy	1d 15h	8:25am	Downtown Greyhound Station	Cheapest
Greyhound Lines, Inc. + FlixBus	Bus	6:20pm	E Osceola Pkwy	1d 14h	8:00am	537-517 W. Jackson Blvd	Fastest
Greyhound Lines, Inc. + FlixBus	Bus	6:20pm	E Osceola Pkwy	1d 16h	9:50am	Chicago 95Th & Dan Ryan	No tags

Last refresh of the prices: Last Saturday at 11:42 PM EST.

Compare 2 ways to go from Kissimmee to Chicago

We recommend taking the bus

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 $125, it presents an excellent value for a comfortable ride.

7bus per day

1d 9hAverage Duration

997 milesDistance

40kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average Price$125 - $349	Average Duration1d 9h	CO₂ emissions 40kg CO₂e
Train	Average Price$192 - $2,401	Average Duration1d 21h	CO₂ emissions 147kg CO₂e

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

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

FlixBus

3.5/512,162 reviews

Staff4.1

Timeliness3.9

Cleanliness4.1

Wifi2.7

Flixbus is a European bus operator that offers intercity and bus travel in over 38 countries. Known for their easy-to-spot lime green buses and for offering affordable transportation between cities in Europe and the Americas, Flixbus is a good option for those looking for an affordable, reliable bus company. In their buses, you'll find free WiFi, bathrooms, and power outlets. You can also pay extra to choose your seat and get extra legroom, or even buy a snack or drink onboard directly from the driver. You can reschedule your ticket for a small fee, which varies from $1 to $5, depending on how close you are to the departure date.

Greyhound

3.5/587,518 reviews

Staff3.6

Timeliness2.9

Cleanliness3.4

Wifi2.5

Greyhound Lines offers the most comprehensive intercity bus services in the United States. They operate a modern, environmentally friendly fleet that serves more than 2400 destinations and carries nearly 16 million passengers annually. When traveling with them, you can expect free WiFi, onboard entertainment, bathrooms, power outlets and decent legroom. One of the great perks of Greyhound is that they connect big cities and smaller towns in the US, where you usually can't get to by train or plane. If you're looking for safe and affordable transportation, Greyhound is a great choice.

Greyhound Kissimmee Chicago recent customer reviews

They were awesome

Tremayne B.

July 8, 2021

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

Frequently asked questions about traveling 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 $125. The average price for this route is around $169. 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 trip duration from Kissimmee to Chicago is 1d 9h, covering a distance of 997 miles (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?
Several major bus companies operate on this route with 7 buses available per day, including services from FlixBus, Greyhound.
What is the earliest and latest departure time 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 recommended mode of travel 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 reviews on Busbud, the bus company FlixBus has the best Wi-Fi rating with a score of 2.7.
Which bus company has the most timely service from Kissimmee to Chicago?
According to Busbud traveler reviews, the most timely 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 traveler 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

01/27

No data

01/28

No data

Today

$167

01/30

$143

01/31

$206

02/01

$130

02/02

No data

02/03

No data

The cheapest trip from Kissimmee to Chicago was searched and found on Feb 1, 2026 with a price of $130

To 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 $130 to $206 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 $130 which is on 2026-02-01.