Next departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
FlixBus + Greyhound Lines, Inc. | E Osceola Pkwy | Downtown Greyhound Station | CheapestFastest | |||||
Greyhound Lines, Inc. + FlixBus | E Osceola Pkwy | Downtown Greyhound Station | No tags | |||||
Greyhound Lines, Inc. + FlixBus | E Osceola Pkwy | 537-517 W. Jackson Blvd | No tags | |||||
FlixBus + Greyhound Lines, Inc. | E Osceola Pkwy | Chicago 95Th & Dan Ryan | No tags | |||||
Greyhound Lines, Inc. + FlixBus | E Osceola Pkwy | Chicago 95Th & Dan Ryan | No tags |
Last refresh of the prices: Last Friday at 8:38 AM EDT.
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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 10 minutes, and with fares starting at just $148, it presents an excellent value for a comfortable ride.
Bus Kissimmee to Chicago: Trip Overview
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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?
Frequently asked questions on the trip Kissimmee - Chicago
What is the distance between Kissimmee and Chicago?
The distance between Kissimmee and Chicago is approximately 1611 km (999 miles).
What are the departure and arrival locations for buses traveling from Kissimmee to Chicago?
Buses departing from E Osceola Pkwy in Kissimmee will take you to Downtown Greyhound Station in Chicago.
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 Nov 2, 2025 with a price of $226To 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 $226 to $229 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 $226 which is on 2025-11-07.
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 destinationTop travelled bus routes
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Popular Buses Connecting Kissimmee
Buses Leaving from Kissimmee
- Bus from Kissimmee to Orlando
- Bus Kissimmee - Miami
- Kissimmee - Miami
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- Bus from Kissimmee to Fort Pierce
- Bus Kissimmee - Sarasota
- Kissimmee - Newark
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- Bus Kissimmee - Lake Worth
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Buses Going to Kissimmee
- Bus from Orlando to Kissimmee
- Bus Tampa - Kissimmee
- Miami - Kissimmee
- Bus from Miami to Kissimmee
- Bus Jacksonville - Kissimmee
- Jacksonville - Kissimmee
- Bus from Venice to Kissimmee
- Bus Charlotte - Kissimmee
- Port Saint Lucie - Kissimmee
- Bus from Atlanta to Kissimmee
- Bus Pompano Beach - Kissimmee
- Naples - Kissimmee
- Bus from Columbus to Kissimmee
- Bus Fort Lauderdale - Kissimmee
- St. Petersburg - Kissimmee
Popular Buses Connecting Chicago
Buses Leaving from Chicago
- Bus from Chicago to Columbia
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- Bus from Chicago to New York City
- Bus Chicago - South Bend
- Chicago - St. Louis
- Bus from Chicago to Milwaukee
- Bus Chicago - Kankakee
- Chicago - Champaign
Buses Going to Chicago
- Bus from Boston to Chicago
- Bus Toronto - Chicago
- Atlanta - Chicago
- Bus from Indianapolis to Chicago
- Bus Bridgeport - Chicago
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- Bus from Madison to Chicago
- Bus New York City - Chicago
- Champaign - Chicago
- Bus from Buffalo to Chicago
- Bus Minneapolis - Chicago
- Savannah - Chicago
- Bus from Cambridge to Chicago
- Bus Philadelphia - Chicago
- Ontario - Chicago
Popular routes in this country
- Bus from Washington to New York City
- Bus Boston - New York City
- New York City - Boston
- Bus from Philadelphia to New York City
- Bus Niagara Falls - New York City
- Buffalo - New York City
- Bus from Baton Rouge to New Orleans
- Bus Baltimore - New York City
- Atlanta - Savannah
- Bus from Albany to New York City
- Bus New York City - Burlington
- Las Vegas - Los Angeles
- Bus from Detroit to Chicago
- Bus Los Angeles - San Diego
- Miami - Orlando