score:6
I would pick Pune for a few reasons:
Upvote:1
I would recommend Pune as I am from Pune. You said you are coming for work so Pune is the best option you have instead of Chennai. And who said Pune don't have it's own airport but it is not International Airport but Mumbai is just 2 and half hour away from Pune. Pune is Hub for IT and Education. All over and some abroad people comes to Pune for education and for business as well. You were right, the weather is just awesome here. DO come in winter season.
Upvote:4
I have actually spent 1 year in both Pune and Chennai working for an IT company and i hope my experience would be helpful to you
Chennai is city which has over the past few years become more cosmopolitan than it was a decade ago. But still if you are not aware of South Indian languages such as Tamil, Telegu etc. you will have a hard time communicating in Chennai. Although most of the people will speak English so you should manage to get around and communicate with the help of few hand language and broken simple English conversations.
Pune on the other hand has been more close to Mumbai and hence you would find very easy to communicate in English and you get around easily. As it is close to Mumbai - you should not have much problems in travelling to kashmir, Delhi etc. which are closer, cheaper and have more options to travel when compared to Chennai.
My advice to you would be to make Pune as the base location and travel to Chennai, Pondicherry, Mahabalipuram for diversity of culture and do visit ECR highway (East Coast Road) for its scenic beauty.