Bus Tickets from Chicago to Kissimmee

Next departures

Next departures for Chicago to Kissimmee on November 8
Operated byVehicle typeDeparture timeDeparture locationTrip durationArrival timeArrival locationRecommendedPrice and booking link
Greyhound Lines, Inc. + FlixBus
    		Chicago 95Th & Dan Ryan
    		E Osceola PkwyCheapest
    FlixBus + Greyhound Lines, Inc.
      		Chicago 95Th & Dan Ryan
      		E Osceola PkwyFastest
      Greyhound Lines, Inc. + FlixBus
        		Downtown Greyhound Station
        		E Osceola PkwyNo tags
        FlixBus
          		Downtown Greyhound Station
          		E Osceola PkwyNo tags
          Greyhound Lines, Inc.
            		537-517 W. Jackson Blvd
            		E Osceola PkwyNo tags

            Last refresh of the prices: Yesterday at 11:16 AM CST.

            Compare 2 ways to go 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, 6 hours 5 minutes, and with fares starting at just $159, it presents an excellent value for a comfortable ride.

            8bus per day
            1d 6hAverage Duration
            1592 kmDistance
            40kgCO₂ emissions
            Bus
            		Average Price$159 - $552Average Duration1d 6h
            40kg CO₂e
            Train
            		Average Price$192 - $761Average Duration1d 14h
            147kg CO₂e

            Frequently asked questions about travelling from Chicago to Kissimmee by bus

            1. What is the travel distance from Chicago to Kissimmee?

              The distance between Chicago and Kissimmee is approximately 1611 km (999 miles).

            2. What are the departure and arrival locations for buses traveling from Chicago to Kissimmee?

              Buses departing from Downtown Greyhound Station in Chicago will take you to E Osceola Pkwy in Kissimmee.

            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
            $243
            11-07
            $234
            Today
            $250
            11-09
            No data
            11-10
            No data
            11-11
            No data
            11-12
            No data
            11-13
            No data
            busbud logoThe cheapest trip from Chicago to Kissimmee was searched and found on Nov 7, 2025 with a price of $234

            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.

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

            busbud logoThe bus is the cheapest travel choice for this destination

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