What is the cheapest way to get from Windsor to Chepstow?

The cheapest way to get from Windsor to Chepstow is to fly which costs £140 - £650 and takes 14h 17m.

What is the fastest way to get from Windsor to Chepstow?

The fastest way to get from Windsor to Chepstow is to fly and train which takes 13h 46m and costs £330 - £1,200.

How far is it from Windsor to Chepstow?

The distance between Windsor and Chepstow is 3732 miles.

How long does it take to get from Windsor to Chepstow?

It takes approximately 15h 56m to get from Windsor to Chepstow, including transfers.

What is the time difference between Windsor and Chepstow?

Chepstow is 4h ahead of Windsor. It is currently 5:58 PM in Windsor and 9:58 PM in Chepstow.

Where can I stay near Chepstow?

There are 1959+ hotels available in Chepstow.

Windsor to Chepstow - 7 ways to travel via train, and plane

There are 7 ways to get from Windsor to Chepstow by plane or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

Fly Detroit to Cardiff Airport, train
best
1. Fly from Detroit (DTW) to Cardiff Airport (CWL)plane DTW - CWL
2. Take the train from Cardiff Central to Chepstowtrain
15h 56m
£228–931
Fly Detroit to Bristol Airport
cheapest
1. Fly from Detroit (DTW) to Bristol Airport (BRS)plane DTW - BRS
14h 17m
£142–624
Fly Detroit to London Heathrow Airport, train
1. Fly from Detroit (DTW) to London Heathrow Airport (LHR)plane DTW - LHR
2. Take the train from London Paddington to Newport (S Wales)train
13h 46m
£332–1,119
Fly Detroit to Birmingham Airport, train
1. Fly from Detroit (DTW) to Birmingham Airport (BHX)plane DTW - BHX
2. Take the train from Birmingham New Street to Chepstowtrain
16h 27m
£373–968
Fly Windsor Airport to London Heathrow Airport, train
1. Fly from Windsor Airport (YQG) to London Heathrow Airport (LHR)plane YQG - LHR
2. Take the train from London Paddington to Newport (S Wales)train
17h 32m
£495–1,372
Train to Toronto Pearson International Airport, fly to Cardiff Airport, train
1. Take the train from Windsor to Toronto Union Stationtrain
2. Fly from Toronto Pearson International Airport (YYZ) to Cardiff Airport (CWL)plane YYZ - CWL
3. Take the train from Cardiff Central to Chepstowtrain
16h 16m
£255–1,002
Fly Windsor Airport to Cardiff Airport, train
1. Fly from Windsor Airport (YQG) to Cardiff Airport (CWL)plane YQG - CWL
2. Take the train from Cardiff Central to Chepstowtrain
15h 12m
£361–1,434

Detroit (DTW) to Cardiff Airport (CWL) flights

23Weekly Planes

12h 42mAverage Duration

£219Cheapest Price

See schedules

Questions & Answers

Map of how to get from Windsor to Chepstow.

Launch map view

Distance: 3,709.9 mi
Duration: 15h 56m

What companies run services between Windsor, ON, Canada and Chepstow, Wales?

Delta, KLM, and three other airlines fly from Detroit (DTW) to Bristol Airport (BRS) 3 times a day.

Airlines

Train operators

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