CrossCountry
Avanti West Coast
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Each fare is the lowest adult economy ticket fare found by our customers on Trainline. Fares booked further in advance than the dates displayed may be cheaper. Prices are updated daily, subject to change and indicative of price last update. Limited availability. Discount cards and coach journeys excluded, prices exclusive of booking fee.
Trains to Chesterfield from Winchester
It takes an average of 3h 30m to travel from Winchester to Chesterfield by train, over a distance of around 150 miles (242 km). There are normally 42 trains per day travelling from Winchester to Chesterfield and tickets for this journey start from £34.40 when you book in advance.
| First train | 11:32 | |
|---|---|---|
| Last train | 11:32 | |
| Departure station | Winchester | |
| Arrival station | Chesterfield | |
| Journey time | From 3h 30m | |
| Distance | 150 miles (242 km) | |
| Frequency | 42 trains per day | |
| Changes | Direct trains available | |
| Price | From £34.40 | |
| Train operators |
What are the train times from Winchester to Chesterfield?
Get from Winchester to Chesterfield in as little as 3 hours 30 minutes on the fastest trains, so you can make the most of your time.
The average train journey from Winchester to Chesterfield takes around 3 hours 30 minutes. There are around 42 trains that operate on this route daily.
There are direct trains running on this popular route from Winchester to Chesterfield every day.
Trains on this route are operated by CrossCountry.
Tickets for this journey start from £34.40. Booking in advance often results in cheaper ticket prices.
With our Journey Planner, you can check live train times, compare prices and check routes.
What do people frequently ask about the train journey from Winchester to Chesterfield?
Want to know more about your journey from Winchester to Chesterfield? We've compiled some of the most frequently asked questions by our customers to help you plan your journey.
How far is the train ride from Winchester to Chesterfield?
Can I take a flight-free trip from Winchester to Chesterfield?
What is the best way to travel to Chesterfield from Winchester?
What time does the first train run from Winchester to Chesterfield?
How late does the train from Winchester to Chesterfield run?
How many trains go from Winchester to Chesterfield per day?
When do tickets from Winchester to Chesterfield go on sale?
Planning a round trip from Winchester to Chesterfield?
How do I find cheap train tickets from Winchester to Chesterfield?
As most UK train companies increase their prices as the departure date approaches, our Trainline team of experts have put together these tips to help you find the cheapest tickets.
1. Book in advance
Train tickets from Winchester to Chesterfield start at £34.40§ one way for a Standard Class ticket if you book in advance. UK train companies usually release Advance tickets up to 12 weeks ahead of time, and these can be cheaper than tickets bought on the day of travel.
2. Sign up to Ticket Alert
If you're planning a trip more than 12 weeks ahead, sign up to our Ticket Alert to get notified when Advance tickets are released for your travel date.
3. Use a Railcard
National Railcards offer a 1/3 off eligible train tickets in the UK and can be a great investment if you travel throughout the year. Buy one with us and you'll be able to store it digitally in our app, so you'll always have it on your travels.
4. Book split tickets
Our handy feature SplitSave will 'split' your train journey into multiple tickets, which can be much cheaper than buying a single ticket. Find out more about split tickets.
5. Travel Off-Peak
If you can be flexible with your travel times, Off-Peak and Super Off-Peak tickets are usually cheaper in the UK. Generally, Off-Peak times are any time at weekends and outside of Monday to Friday morning and evening rush hours.
6. Consider a Season Ticket
Best for commuters, if you catch a train on the same route more than 3 times per week, you could save money with a Season Ticket. With annual, monthly, weekly and flexi options available, find out if a Season Ticket for Winchester to Chesterfield is right for you.
For more money-saving tips on UK and European train travel, read our cheap train tickets guide.
§Advance adult single fare. Excludes booking fee. Prices seen by Trainline customers in the last 30 days. Availability limited.