Find coaches from Chicago to Kissimmee

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Sun15 Jun
Mon16 Jun
from US$164
Tue17 Jun
from US$164
Wed18 Jun
from US$111
Thu19 Jun
from US$100
Fri20 Jun
from US$125
Sat21 Jun
Sun22 Jun

Cheap buses leaving Monday

One passenger / one way

  • This trip is recommended because it is the: Cheapest
    Departure time: 16 June at
    Departure city: Chicago
    Departure location: Chicago 95Th & Dan Ryan
    Arrival time: 18 June at
    Destination city: Kissimmee
    Destination location: E Osceola Pkwy
    Operated by: FlixBus + Greyhound Lines, Inc.
    FlixBus + Greyhound Lines, Inc.
    Vehicle: BusDuration:
  • This trip is recommended because it is the: Fastest
    Departure time: 16 June at
    Departure city: Chicago
    Departure location: Downtown Greyhound Station
    Arrival time: 17 June at
    Destination city: Kissimmee
    Destination location: E Osceola Pkwy
    Operated by: Greyhound Lines, Inc. + FlixBus
    Greyhound Lines, Inc. + FlixBus
    Vehicle: BusDuration:
  • Departure time: 16 June at
    Departure city: Chicago
    Departure location: Downtown Greyhound Station
    Arrival time: 17 June at
    Destination city: Kissimmee
    Destination location: E Osceola Pkwy
    Operated by: Greyhound Lines, Inc. + FlixBus
    Greyhound Lines, Inc. + FlixBus
    Vehicle: BusDuration:
  • Departure time: 16 June at
    Departure city: Chicago
    Departure location: Downtown Greyhound Station
    Arrival time: 18 June at
    Destination city: Kissimmee
    Destination location: E Osceola Pkwy
    Operated by: FlixBusFlixBus
    Vehicle: BusDuration:
  • Departure time: 16 June at
    Departure city: Chicago
    Departure location: 537-517 W. Jackson Blvd
    Arrival time: 17 June at
    Destination city: Kissimmee
    Destination location: E Osceola Pkwy
    Operated by: Greyhound Lines, Inc.Greyhound Lines, Inc.
    Vehicle: BusDuration:

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Compare 2 ways to travel from Chicago to Kissimmee

Bus
Average priceUS$92 - US$305Average duration1d 6h
40kg CO₂e5 out of 5 stars
CheapestFastestMost eco-friendly
Train
Average priceUS$228 - US$529Average duration1d 15h
147kg CO₂e1 out of 5 stars
busbud logoBusbud recommends taking the bus from Chicago to Kissimmee

Among the sustainable travel choices, the bus stands out as a good way to reach Kissimmee. The journey takes about 1 day, 6 hours 5 minutes and with fares starting at just US$92, it presents an excellent value for a comfortable ride.

8bus per day
1d 6hAverage duration
US$92Cheapest ticket
40kgCO₂ emissions

Bus Chicago to Kissimmee: Trip Overview

Average ticket priceUS$190
Average bus trip duration1d 6h
Number of daily buses8
Earliest bus departure06:10
Distance997 miles
Latest bus departure23:59

Chicago to Kissimmee Bus

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

We make sure you can find a bus service from Chicago to Kissimmee from the most reliable bus companies operating this trip.

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

Frequently asked questions on the trip Chicago - Kissimmee

  1. What is the cheapest way to go from Chicago to Kissimmee?

    The price for a coach ticket from Chicago to Kissimmee starts at US$92, though the average is US$190. These prices can change depending on factors like the date, the class and the coach company you choose. Compare the prices and amenities offered by each company on Busbud and find the best deals and offers.

  2. How long does it take to travel from Chicago to Kissimmee by bus?

    The coach journey between Chicago and Kissimmee lasts about 1d 6h. The fastest coach journey typically takes 1d 2h. However, please keep in mind that your specific travel time may vary due to the prevailing traffic conditions along the route.

  3. When is the first coach from Chicago to Kissimmee?

    The first coach from Chicago to Kissimmee leaves at 06:10. Keep in mind that departure times might change on weekends and holidays.

  4. How far is Kissimmee from Chicago by coach?

    The journey from Chicago to Kissimmee by coach covers an approximate distance of 999 miles (1611 km).

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

    To travel from Chicago to Kissimmee without flying, you can take the coaches. Choosing the coach guarantees a comfortable and sustainable travel experience, allowing you to admire the views on your way to your destination. You also have the option of utilising carpooling services.

  6. Is there am overnight bus from Chicago to Kissimmee?

    Yes, you can find coaches leaving until 23:59 and arriving the next day. Remember to bring along some essentials like a snuggly blanket and a few treats for a comfortable trip.

Find cheapest prices for buses

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

Best price found
11/06
US$208
12/06
US$209
Today
US$190
14/06
US$128
15/06
No data
16/06
No data
17/06
US$157
18/06
US$133
busbud logoThe cheapest trip from Chicago to Kissimmee was searched and found on 14 Jun 2025 with a price of US$128

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 US$128 to US$239 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 US$128, which is on 2025-06-14.

Usually Greyhound Lines, Inc. will charge you higher prices for tickets closer to the departure date. To find the best prices, you should be flexible on your date of travel.

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 Chicago to Kissimmee but it'll also be endearing to native speakers who will surely appreciate your effort.

Start sightseeing the minute your bus leaves the station. If you're on the night bus from Chicago to Kissimmee, get comfy and count the stars.

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 Chicago to Kissimmee.

Make a music playlist for your bus ride from Chicago to Kissimmee, and enjoy the scenery to tunes from your own personal soundtrack.

Did you know?

9.2% of ground transportation in Europe is done by bus versus 7.4% by train.

Did you know there are on average 4,400 intercity bus departures every day in the US only? This number has been growing for 9 years in a row, yay!

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 Chicago to Kissimmee?

busbud logoThe bus is the cheapest travel choice for this destination

Will you be returning to Chicago by bus?

Bus from Chicago to Kissimmee

You can also go to Kissimmee by train

Train from Chicago to Kissimmee

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. Use Busbud to book your trip online, in your own language and currency, wherever you are. With Busbud, you can buy tickets with confidence. We ensure that you make the most out of your bus trip by partnering up with reliable bus companies from all around the world such as Greyhound, Eurolines, ALSA, OUIBUS (BlaBlaBus), National Express and many others.

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