Cherrapunji is a really beautiful place. You can visit the ever famous live root double decker bridge, Visit Dawki like a day trip, Entire meghalaya is amazingly beautiful. From Chandigarh you can fly to Kolkata and from Kolkata you can take a flight to Shillong.
There are many waterfalls like Elephant falls, Rainbow falls, then there are view points like Duwan sing syiem view point, khasi hills, then Mawsmai cave, nohkalikai falls, seven sister falls, living root bridges, and the most cleanest village Mawlynnong village. Do visit them all. happy journey! 😃
Wow. That is some distance to drive. The distance is long so one need to plan meticulously for every kind of logistical requirements. And I'm sure, you must have already done so.
In context to Cherrapunji, you need to reach Guwahati first. Then from Guwahati one need to reach Shillong. The drive from Guwahati to Shillong is one of the most serene drive in India, if not the best. This takes about 3 hours to 3.30hours at the max. Now from Shillong on need to move North west to Cherrapunji and this is usually 3hours drive from Shillong. Done this circuit last to last year and wish to go back again with a new itinerary this time. If you need any help in planning or if you need any further details, please feel free to contact me.