The average train between Chesterfield and Winchester takes 3h 27m and the fastest train takes 3h 13m. There is an hourly train service from Chesterfield to Winchester. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.
Trains run hourly between Chesterfield and Winchester. The earliest departure is at 5:10 AM in the morning, and the last departure from Chesterfield is at 10:01 PM which arrives into Winchester at 6:36 AM. All services require a transfer at London St Pancras International and take an average of 3h 27m. The schedules shown below are for the next available departures.


3h 15m • 2 changes


3h 17m • 2 changes


3h 19m • 2 changes


3h 18m • 2 changes


3h 23m • 2 changes


3h 21m • 2 changes


3h 23m • 2 changes


3h 20m • 2 changes


3h 23m • 2 changes


3h 21m • 2 changes


3h 23m • 2 changes


3h 20m • 2 changes
Want to know about travelling from Chesterfield to Winchester? 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 train from Chesterfield to Winchester. However, there are services departing from Chesterfield station and arriving at Winchester station via London St Pancras Intl. The journey, including transfers, takes approximately 3h 27m.
Chesterfield to Winchester train services, operated by East Midlands Railways, depart from Chesterfield station.
Chesterfield to Winchester train services, operated by East Midlands Railways, arrive at Winchester station.
Book your Chesterfield to Winchester train tickets online with East Midlands Railways, London Underground (Tube) and South Western Railway.
The distance between Chesterfield and Winchester is 243 km. The road distance is 355 km.
You can take a train from Chesterfield to Winchester via London St Pancras International, Euston station, Waterloo Station, and London Waterloo in around 3h 42m.