Chandigarh is the closest major city from Shimla. There are hundreds of travellers travelling between the cities on daily bases, there are all kinds of transportation mode available between them including airway. Most used and prominent mode is usually by road. The main route is NH 5. The route is 113 km in distance taking almost 3 and a half hour to cover by means of bus average speed cars.
This route passes through pinjor, kalka Kasauli and solan. Main stopovers is Pinjor garden and timber trail on the way to Shimla. Also other connectivity is via train track which is a longer route and takes almost 5 hours. The total length is around 137 km though you have to change trains Kalka station. It’s a lengthier and time taking option with benefits of nature gifted scenery.