The average bus between Woodstock and Chicago takes 29h 5m and the fastest bus takes 20h 30m. There is at least one bus per day from Woodstock to Chicago. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.
Buses run once daily between Woodstock and Chicago. The earliest departure is at 12:42 PM in the afternoon, and the last departure from Woodstock is at 5:55 PM which arrives into Chicago at 6:10 AM. All services require a transfer at Kingston and take an average of 29h 5m. The schedules shown below are for the next available departures.
Arrives next day



30h 13m • 3 changes
Arrives +2 days



36h 15m • 3 changes
Arrives next day



24h 43m • 3 changes
Arrives +2 days



36h 15m • 3 changes
Want to know about travelling from Woodstock to Chicago? 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.
No, there is no direct bus from Woodstock to Chicago. However, there are services departing from Woodstock station and arriving at Chicago station via New York. The journey, including transfers, takes approximately 29h 5m.
Woodstock to Chicago bus services, operated by Trailways, depart from Kingston station.
Woodstock to Chicago bus services, operated by Trailways, arrive at Chicago Bus Station.
The distance between Woodstock and Chicago is 1,116.1 km. The road distance is 1,637 km.
You can take a bus from Woodstock to Chicago Bus Station via Kingston, New York, Port Authority Bus Terminal, and Newark Penn Station in around 20h 47m.