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Chesapeake to Kissimmee buses

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Trip Overview

The average bus between Chesapeake and Kissimmee takes 27h 59m and the fastest bus takes 27h 56m. The bus runs, on average, 5 times per week from Chesapeake to Kissimmee. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

27h 59m
Duration
825 mi
Distance
$166
Average price
5 times a week
Frequency

Chesapeake to Kissimmee bus times

Buses run 5 times a week between Chesapeake and Kissimmee. The earliest departure is at 11:50 AM in the morning, and the last departure from Chesapeake is at 11:51 AM which arrives into Kissimmee at 3:47 PM. All services require a transfer at Military Circle Mall and take an average of 27h 59m. The schedules shown below are for the next available departures.

Departing Tuesday, November 3, 2026

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    Arrives next day

    Hampton Roads Transit (HRT)Hampton Roads Transit (HRT)Greyhound USAFlixbus USAFlixbus USALynx Central Florida Transport28h • 5 changes

Departing Wednesday, November 4, 2026

  •  → 

    Arrives next day

    Hampton Roads Transit (HRT)Hampton Roads Transit (HRT)Greyhound USAFlixbus USAFlixbus USALynx Central Florida Transport28h • 5 changes

Departing Thursday, November 5, 2026

  •  → 

    Arrives next day

    Hampton Roads Transit (HRT)Hampton Roads Transit (HRT)Greyhound USAFlixbus USAFlixbus USALynx Central Florida Transport28h • 5 changes

Departing Friday, November 6, 2026

  •  → 

    Arrives next day

    Hampton Roads Transit (HRT)Hampton Roads Transit (HRT)Greyhound USAFlixbus USAFlixbus USALynx Central Florida Transport27h 58m • 5 changes

Departing Saturday, November 7, 2026

  •  → 

    Arrives next day

    Hampton Roads Transit (HRT)Hampton Roads Transit (HRT)Greyhound USAFlixbus USAFlixbus USALynx Central Florida Transport27h 56m • 5 changes

Frequently asked questions

Want to know about travelling from Chesapeake to Kissimmee? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.

Map of how to get from Chesapeake to Kissimmee.ExpandLaunch map view
  • Distance: 824.6 mi
  • Duration: 27h 59m

What companies run services between Chesapeake, City of Chesapeake, VA, USA and Kissimmee, FL, USA?

You can take a bus from Dntc to N Main St & W Cypress St via Military Circle Mall, Military & Poplar Hall, Norfolk, Raleigh Bus Station, Orlando Bus Station, Orlando, and Florida Mall in around 20h 36m.

Operators