Is there a way to reach Chicago from Kissimmee without flying?

Both buses and trains are available for traveling between these two cities. Both are easy and sustainable ways to travel to Chicago. Another option is using carpool services and riding with fellow travelers.

How long does it take to get to Chicago from Kissimmee by bus?

Traveling from Kissimmee to Chicago takes about 1d 4h on average, but you can get there in as little as 1d 3h with the quickest bus. This is the time it takes to travel the 999 miles (1611 km) that separate the two cities.

What is the distance between Kissimmee and Chicago?

Kissimmee and Chicago are 999 miles (1611 km) apart.

What are the departure and arrival stations when taking the bus from Kissimmee to Chicago?

If you're headed to Chicago from Kissimmee, chances are that your bus will depart from E Osceola Pkwy and arrive at Downtown Greyhound Station. These are the main departure and arrival locations on this route, but you can also find other options that could better fit your plans.

What is the most affordable way to get from Kissimmee to Chicago?

Go for the bus if you want the most economical way to travel this route. With prices starting at $128, you won't find a more affordable way to get there.

What is the ticket price for the bus trip from Kissimmee to Chicago?

The bus ticket costs $199 on average. In the last 30 days, the prices ranged from $128 to $359, so it's good to do your research before booking.

What are the best sights and things to do in Chicago?

Once in Chicago, you can start exploring the city and discover its surroundings. The top sights and things to do are Lincoln Park Zoo, Chicago Shakespeare Theater on Navy Pier, Brookfield Zoo, Museum of Contemporary Art and Navy Pier.

Is it possible to travel by overnight bus from Kissimmee to Chicago?

Yes, it is possible to take an overnight bus from Kissimmee to Chicago. Make sure to pack a blanket and a snack to make your trip more comfortable.

Bus Kissimmee to Chicago from $139 | Compare & Save up to 35%

TodayJun 15

from $165

TomorrowJun 16

from $174

TueJun 17

from $164

WedJun 18

from $146

ThuJun 19

from $102

FriJun 20

from $121

SatJun 21

from $138

SunJun 22

Cheap buses leaving tomorrow

One passenger / one way

This trip is recommended because it is: Cheapest
Departure time: June 16 at 8:25pm
Departure city: Kissimmee
Departure location: E Osceola Pkwy
Arrival time: June 17 at 11:50pm
Destination city: Chicago
Destination location: Chicago 95Th & Dan Ryan
Operated by: FlixBus
Vehicle: BusDuration: 1d 4h
This trip is recommended because it is: Fastest
Departure time: June 16 at 5:20pm
Departure city: Kissimmee
Departure location: E Osceola Pkwy
Arrival time: June 17 at 8:10pm
Destination city: Chicago
Destination location: Downtown Greyhound Station
Operated by: FlixBus + Greyhound Lines, Inc.
FlixBus + Greyhound Lines, Inc.
Vehicle: BusDuration: 1d 3h
Departure time: June 16 at 10:55am
Departure city: Kissimmee
Departure location: E Osceola Pkwy
Arrival time: June 17 at 2:35pm
Destination city: Chicago
Destination location: Downtown Greyhound Station
Operated by: FlixBus + Greyhound Lines, Inc.
FlixBus + Greyhound Lines, Inc.
Vehicle: BusDuration: 1d 4h
Departure time: June 16 at 8:25pm
Departure city: Kissimmee
Departure location: E Osceola Pkwy
Arrival time: June 18 at 12:10am
Destination city: Chicago
Destination location: Downtown Greyhound Station
Operated by: FlixBus
Vehicle: BusDuration: 1d 4h
Departure time: June 16 at 5:20pm
Departure city: Kissimmee
Departure location: E Osceola Pkwy
Arrival time: June 17 at 8:10pm
Destination city: Chicago
Destination location: Downtown Greyhound Station
Operated by: FlixBus + Greyhound Lines, Inc.
FlixBus + Greyhound Lines, Inc.
Vehicle: BusDuration: 1d 3h

Accepted payments

Compare 2 ways to go from Kissimmee to Chicago.

	Average Price	Average Duration	CO₂ emissions
Bus	Average Price$128 - $359	Average Duration1d 4h	CO₂ emissions 40kg CO₂e5 out of 5 stars	CheapestFastestMost eco-friendly
Train	Average Price$281 - $1,578	Average Duration1d 20h	CO₂ emissions 147kg CO₂e1 out of 5 stars

Busbud recommends taking the bus from Kissimmee to Chicago

Among the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 1 day, 4 hours 40 minutes and with fares starting at just $128, it presents an excellent value for a comfortable ride.

8.615384615384615bus per day

1d 4hAverage Duration

$128Cheapest ticket

40kgCO₂ emissions

Bus Kissimmee to Chicago: Trip Overview

Average ticket price$199

Average bus trip duration1d 4h

Number of daily buses8

Earliest bus departure10:55am

Distance997 miles (1608 km)

Latest bus departure11:40pm

Compare bus companies

FlixBus

3.5/59,058 reviews

Staff4.1

Timeliness4

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

3.5/587,034 reviews

Staff3.6

Timeliness2.8

Cleanliness3.3

Wifi2.3

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, Greyhound, Tornado Bus, Los Limousines, Valley Transit, Tufesa, Wanda Coach

Kissimmee to Chicago Bus

Busbud shows you the best bus ticket fares and bus schedules so you can easily plan and book a trip by bus from Kissimmee to Chicago.

Bus service from Kissimmee to Chicago will be provided by the most trusted bus companies.

Whether it is cheap bus tickets or more luxurious buses going to Chicago from Kissimmee, we help you find what you're looking for based on how much of a budget you have.

Where are the popular stops in Kissimmee and Chicago?

Stops in Kissimmee

A - E Osceola Pkwy

B - Kissimmee Station

C - Denny's

D - Irlo Bronson Memorial Hwy McDonald's

E - Davenport Days Inn

Stops in Chicago

A - Downtown Greyhound Station

B - Chicago O'Hare International Airport

C - Polk St & Canal St

D - Tornado Bus S Kedzie Ave

E - Cumberland CTA

F - Turimex California Ave

Frequently asked questions for your trip Kissimmee - Chicago

Is there a way to reach Chicago from Kissimmee without flying?
How long does it take to get to Chicago from Kissimmee by bus?
What is the distance between Kissimmee and Chicago?
What are the departure and arrival stations when taking the bus from Kissimmee to Chicago?
What is the most affordable way to get from Kissimmee to Chicago?
What is the ticket price for the bus trip from Kissimmee to Chicago?
What are the best sights and things to do in Chicago?
Is it possible to travel by overnight bus from Kissimmee to Chicago?

Find cheapest prices for buses

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

06/13

$180

06/14

No data

Today

$167

06/16

$167

06/17

$157

06/18

$139

06/19

$157

06/20

$157

The cheapest trip from Kissimmee to Chicago was searched and found on Jun 18, 2025 with a price of $139

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 $139 to $270 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 $139 which is on 2025-06-18.

About Bus Travel

Bus Travel Tips

If you're abroad, study some local language. Not only could it get you out of a pickle during your bus trip from Kissimmee to Chicago but it'll also be endearing to native speakers who will surely appreciate your effort.

Much more than a mere vehicle taking you from Kissimmee to Chicago, riding the bus will expose you to some of the most stunning panoramas while enroute to your final bus stop.

Buses are energy-efficient. Carrying a passenger over 100 kms by coach only takes 0.6-0.9 liters of gas. Compare that to the 2.6 liters required by high-speed train, 6.6 liters by airplane and 7.6 liters by gas-powered car, and it's clear that the bus is a more environmentally-conscious option for your bus transportation from Kissimmee to Chicago.

Create your own real life musical score by curating a personalized bus travel playlist - the perfect accompaniment to your bus ride from Kissimmee to Chicago.

Did you know?

Did you know some bus companies in Germany offer to their passenger low-costs snacks and regional beer based on their destination? Prosit!

The average number of passengers on a coach bus is 32 meaning that a bus could replace a minimum of at least 30 cars!

The word 'bus' is an abbreviation of 'omnibus" which means 'for all' in Latin as buses were meant to be transportation for everybody.

What's the cheapest way to go from Kissimmee to Chicago?

The bus is the cheapest travel choice for this destination

Vehicle Type	Travel Time	Avg Price	Daily Departures
Vehicle TypeBus	Travel Time1d 4h	Avg Price$199	Daily Departures8
Vehicle TypeTrain	Travel Time1d 20h	Avg Price$386	Daily Departures3

Will you be returning to Kissimmee by bus?

Bus from Kissimmee to Chicago

You can also go to Chicago by train

Train from Kissimmee to Chicago

Top traveled bus routes

Why choose Busbud?

The Best Way To Book Bus and Train Tickets

Busbud.com makes it easy for you to find, compare and book city-to-city bus tickets, all over the world. We save you the extra trip to the bus station. With Busbud, wherever you go, you have a worldwide bus station within reach and available in your own language and currency. Busbud prides itself on its worldwide partnerships. We make it possible for you to buy tickets with its large network of trustworthy bus partners like Greyhound, Eurolines, ALSA, OUIBUS (BlaBlaBus), National Express and many others.

One passenger / one way

Cheap buses leaving tomorrow

One passenger / one way

One passenger / one way

One passenger / one way

One passenger / one way

One passenger / one way

One passenger / one way

Compare 2 ways to go from Kissimmee to Chicago.

Bus Kissimmee to Chicago: Trip Overview

Compare bus companies

Kissimmee to Chicago Bus

Where are the popular stops in Kissimmee and Chicago?

Frequently asked questions for your trip Kissimmee - Chicago

Is there a way to reach Chicago from Kissimmee without flying?

How long does it take to get to Chicago from Kissimmee by bus?

What is the distance between Kissimmee and Chicago?

What are the departure and arrival stations when taking the bus from Kissimmee to Chicago?

What is the most affordable way to get from Kissimmee to Chicago?

What is the ticket price for the bus trip from Kissimmee to Chicago?

What are the best sights and things to do in Chicago?

Is it possible to travel by overnight bus from Kissimmee to Chicago?

Find cheapest prices for buses

About Bus Travel

Bus Travel Tips

Did you know?

What's the cheapest way to go from Kissimmee to Chicago?

Will you be returning to Kissimmee by bus?

You can also go to Chicago by train

Top traveled bus routes

Why choose Busbud?

The Best Way To Book Bus and Train Tickets

People from around the world trust Busbud

Popular Buses Connecting Kissimmee

Buses Leaving from Kissimmee

Buses Going to Kissimmee

Popular Buses Connecting Chicago

Buses Leaving from Chicago

Buses Going to Chicago

Popular routes in this country

Popular airport transfers