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Trains from Chesterfield to
Winchester

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Chesterfield to Winchester by train

A train trip from Chesterfield to Winchester takes about 4hrs 19 mins on average, covering roughly 150 miles (241 kilometres). With around 34 trains running each day, there's plenty of flexibility for your travel plans. If you book in advance, you can grab tickets starting from just £23.10, making it a budget-friendly option for those who plan ahead.

Chesterfield to Winchester Key Stats

Arrival Station

Winchester

Departure Station

Chesterfield

Frequency

34trains
per day

Journey Time

from3hrs 42 mins

Changes

2-2no direct
trains

First Train / Last Train

05:43 / 00:17

Distance

150miles
(241 km)

3 Routes

5 Train Operators

Prices

from£23.10

Travelling from Chesterfield to Winchester by Train

Hop on a Train from Chesterfield to Winchester – It’s Faster Than You Think!

Planning to travel from Chesterfield to Winchester by train? Well, you've come to the right place – and don’t worry, it won’t take forever!

On average, the journey takes around 4hrs 19 mins. But if you’re in a hurry (or just really eager to get to Winchester), the fastest trains can whisk you there in just 3hrs 42 mins. With roughly 34 trains running every day, you're spoiled for choice. This scenic 150-mile (241 km) journey usually requires just one change. You’ll be in the good hands of East Midlands Railway, Avanti West Coast, West Midlands Trains, South Western Railway, CrossCountry, all of whom offer comfy seats and plenty of luggage space – because, let’s face it, nobody likes a cramped train!

The best part? Tickets start from just £23.10 if you book in advance, which is a much better deal than scrambling for tickets on the day. Want to save even more? Travelling during Off-Peak hours or flashing a Railcard can help you keep more money in your wallet.

So, ready to snag those cheap tickets? Use our Journey Planner to find the latest prices and make your wallet happy. Keep scrolling for more travel tips, or check out our timetable above for live train times. Time to choo-choo your way to Winchester!

Journey Details

Frequently asked questions about journeys between Chesterfield and Winchester

Curious about your trip from Chesterfield to Winchester? We've put together answers to the most commonly asked questions from our customers to make planning your journey easier.

How long does it take to travel between Chesterfield and Winchester by train?

The travel time between Chesterfield and Winchester by train varies depending on the type of train and the route, but the average journey time is 4hrs 19 mins & the fastest journey takes 3hrs 42 mins.

What's the fastest journey time between Chesterfield and Winchester by train?

The fastest journey time by train from Chesterfield to Winchester is 3hrs 42 mins.

How much does the train from Chesterfield to Winchester cost?

Train ticket prices from Chesterfield to Winchester can start from as little as £23.10 when you book in advance. The cost of tickets can vary depending on the time of day, route and class you book and are usually more expensive if you book on the day.

What are the departure and arrival times for trains between Chesterfield and Winchester?

The departure and arrival times for trains between Chesterfield and Winchester vary depending on the day of the week and the type of train. Generally, there are around 34 departures and arrivals throughout the day. The first departure is 05:43, and the last train of the day leaves at 00:17.

What is the difference between first class and standard class on trains between Chesterfield and Winchester?

First class tickets on trains between Chesterfield and Winchester typically offer more space, complimentary food and drink, and other amenities compared to standard class.

What amenities are available on trains between Chesterfield and Winchester?

Amenities on trains between Chesterfield and Winchester can include free Wi-Fi, power outlets, onboard catering, and comfortable seating.

What is the cheapest way to travel from Chesterfield to Winchester by train?

By booking your tickets on traintickets.com! There are many ways to save on the cost of train travel between Chesterfield and Winchester. On traintickets.com, we do all the work for you to find the cheapest way possible to get to Winchester, and can save you up to 90%! Simply search for your journey, and be assured we have found you the best possible price.

Is it possible to take a direct train from Chesterfield to Winchester?

No, unfortunately there are no direct trains between Chesterfield & Winchester. However, there are 34 possible journeys which require a change.

What train companies run services from Chesterfield to Winchester?

East Midlands Railway, Avanti West Coast, West Midlands Trains, South Western Railway and CrossCountry are the main train operating companies running services between Chesterfield and Winchester.

Can I bring luggage on board trains between Chesterfield and Winchester?

Yes, you can bring luggage on board trains between Chesterfield and Winchester, but there may be limits on the number of bags or the size and weight of your luggage.

When are Chesterfield to Winchester Train Times?

Check out the upcoming trains from Chesterfield to Winchester on Monday 9th June 2025, with our handy timetable below.

Alternatively, you can view the full day's schedule or search for a different date here!

Monday 9th June
DepartsArrivesChangesVia StationsDurationOperator
12:12 Chesterfield16:04 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 52 mins Get Tickets
12:49 Chesterfield16:32 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 43 mins Get Tickets
13:13 Chesterfield17:04 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 51 mins Get Tickets
13:49 Chesterfield17:34 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 45 mins Get Tickets
14:12 Chesterfield18:02 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 50 mins Get Tickets
14:49 Chesterfield18:32 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 43 mins Get Tickets
15:12 Chesterfield19:02 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 50 mins Get Tickets
15:49 Chesterfield19:33 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 44 mins Get Tickets
16:13 Chesterfield20:04 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 51 mins Get Tickets
16:49 Chesterfield20:31 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 42 mins Get Tickets
17:14 Chesterfield21:04 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 50 mins Get Tickets
17:45 Chesterfield21:32 Winchester2 changesLondon St Pancras International
London Waterloo
3 hrs 47 mins Get Tickets
Search all times & prices for today

What are my cheap ticket options for Chesterfield to Winchester journeys?

From booking in Advance, to our FairSplits, here are our tips for you to find the best price

Advance Tickets

A single ticket for one journey leaving at a specific date and time.

The rule is: the sooner you book the cheaper they are. Usually the cheapest, but least flexible.

Advance fares from Chesterfield to Winchester start from as little as £23.10

Off-Peak & Super Off-Peak Tickets

Offering greater flexibility than Advances, Off-Peak tickets offer travel during less busy times of day trading off more flexibility in the Off-Peak windows but for still discounted fares.

Off Peak fares from Chesterfield to Winchester start from £122.00 one way, or £123.20 return

Anytime Tickets

Anytime tickets are fully flexible allowing travel at any time of the day. Brilliant if you don’t want the pressure of clock watching, returning when you want

Anytime fares from Chesterfield to Winchester are available for £126.60 one way, or £253.00 return

With our FairSplit technology, you can save up to 90% on the cost of train travel.

Split ticketing means that instead of purchasing one rail ticket for your journey we automatically find and help you book two or more tickets instead, covering exactly the same journey. We call it our FairSplit.

Travelling in a group? We can save you even more!

Unlike other split ticketing sites, you can enter multiple railcards in a single search on traintickets.com. We will find you the best price using all possible combinations of your railcards in conjunction with our split ticketing technology & GroupSave.

When you do a search on traintickets.com we check all the cheapest prices automatically

Everything you need to know about Chesterfield Station

Welcome to Chesterfield Train Station

Chesterfield Train Station is a bustling transportation hub nestled in the heart of Derbyshire, UK. Whether you’re a local commuter or an adventurous traveller, Chesterfield Station serves as a gateway to both nearby locales and distant destinations. From its charming town centre, rich with history and vibrant markets, to the alluring peaks of the nearby Pennine Way, this station connects countless journeys. The station offers modern amenities and facilities to cater to diverse needs, making it a preferred choice for many.

Facilities at Chesterfield Train Station

Chesterfield Station is equipped with facilities designed for a smooth and comfortable travel experience. The ticket office opens early, ranging from 05:15 on weekdays to 08:30 on Sundays, providing ample opportunity to purchase or collect pre-booked tickets from our accessible ticket machines. Smartcard holders are in luck, as smartcard validators are available, ensuring a swift and hassle-free start to your journey.

Accesibility is a top priority, with step-free access available throughout the station. From tactile paving to lift services, Chesterfield Station ensures all passengers, including those with mobility impairments, can navigate with confidence. Additionally, passengers can make use of the accessible toilets and baby changing facilities located on Platform 1.

Onward Travel Options

Once at Chesterfield Station, travellers can effortlessly transition to other transport modes. If you’re planning a visit to the picturesque Chatsworth House, you can hop on the 170 or X70 bus just outside the station. For more exploration, taxis are conveniently stationed at the front, and a seamless rail replacement service operates from this point as well, making it simple to get to where you’re going. Click here for more information on onward journeys.

Explore Popular Destinations from Chesterfield

Chesterfield is a starting line to countless adventures. Frequent services to major cities and attractions make it a strategic link for exploring the UK. Whether you're commuting to the dynamic city of Sheffield or planning a getaway to the iconic London St Pancras International, Chesterfield has you covered. Discover historic Nottinghams architecture or soak in the grandeur of Derby. For nature lovers, a trip to Peak District National Park via the nearby town of Dronfield is just a train ride away.

For those interested in extended travel, Chesterfield also offers connections to bustling hubs like Birmingham New Street and Leeds, as well as quiet retreats in Meadowhall, Alfreton, and even the cultural allure of York. Explore these routes further to make the most of your journey.

Conclusion: Start Your Journey at Chesterfield

Chesterfield Train Station, with its strategic connections and appealing amenities, is more than just a stop on the map. It’s a doorway to exploration, whether you’re travelling for business, leisure, or adventure. Its convenient facilities ensure a hassle-free experience, inviting travellers to seamlessly embark on journeys near and far.

So why wait? Dive into the scenic views or the urban buzz awaiting you at your destination with tickets readily available at Chesterfield Train Station. Explore your travel options with ease and make Chesterfield your next station of choice.

Everything you need to know about Winchester Station

Welcome to Winchester Train Station

Exploring the charming city of Winchester by train brings an enjoyable experience, made even better by the excellent facilities at Winchester train station. Known for its historical significance and stunning architecture, Winchester is easily accessible for both residents and tourists via its well-connected rail station. If you're planning a trip—or simply passing through—you'll find a comprehensive network of facilities designed to make your travel smoother and more enjoyable. Let’s take a closer look at what Winchester train station has to offer.

Facilities and Amenities

Winchester train station is equipped with various amenities to ensure your journey is as comfortable as possible. Buying tickets is a breeze with the ticket office open from early morning to late evening, seven days a week. If you've pre-booked your tickets online, you can easily collect them from one of the accessible ticket machines on site. Benefit from the option to use smartcards, which are available for both issuance and validation at the station.

For passengers requiring assistance, staff help is readily available throughout operational hours. The station provides step-free access to all platforms, accommodating those with mobility impairments. There's also a heated waiting room on platform 2 complete with seating that aligns with the Code of Practice, making waits much more pleasant.

When hunger strikes, enjoy a cup of coffee or a quick snack at one of the onsite refreshment facilities like Costa Coffee or the Pumpkin Café. Plus, those who prefer cycling can take advantage of the secure cycle hub available at the station, which provides a large number of spaces and round-the-clock access.

Onward Travel Options

Continuing your journey beyond Winchester is straightforward with numerous transport links at your disposal. Whether you need a bus or a taxi, the station's connectivity ensures ease of travel. Rail replacement services are accessible from the Station Hill Bus Stop, and detailed bus travel information is available online, ensuring you're well-prepared for the next leg of your trip.

Exploring Popular Destinations

With regular train services, reaching popular destinations from Winchester is simple and convenient. You might catch a train to London Waterloo for a day in the capital, or head to the south coast with services to Southampton Central. For a short trip, consider hopping over to Eastleigh or if you're jetting off somewhere, Southampton Airport Parkway is just a short ride away.

Fancy a beach excursion? Trains to Bournemouth are your ticket to summer fun. If reading and culture are calling, Reading offers a substantial array of activities just a train journey away.

Your Journey Awaits

The essence of Winchester is woven into every aspect of its train station, providing a perfect gateway to adventure or a pleasant pit-stop en route to your destination. Whether stepping off the train to explore this historic city or continuing your journey to distant places, Winchester station is set up to meet your travel needs efficiently and comfortably. Next time you find yourself planning a trip through Hampshire, be sure to include a stop at Winchester Train Station—your journey awaits!

Looking for more inspiration?

Popular places to travel by train from Chesterfield