Stopover cities

@rpbourne

So my question is, which of these cities are most interesting for 2-3 days?

Kolkata.

Kochi no longer looks like a small town with an old mix of cultures, it looks like a huge modern city of concrete blocks.

There's a big difference between Kochi and Fort Cochin. Always stay in Fort Cochin and explore that. Kochi is just a stock-standard 'horrible' Indian city.

Chennai

Has not much of interest to the average traveller. It could however be a place to pitch up to Puducherry or Mamallapuram (Mahabalipuram) https://www.lonelyplanet.com/india/tamil-nadu/mamallapuram-mahabalipuram
https://www.lonelyplanet.com/india/tamil-nadu/puducherry-pondicherry

I like a town with a lot of historic/old buildings. Dense older neighborhoods, sometimes with some paint peeling/dirt around the edges. I love markets with street food. If there is some palace or temple that is really amazing, I'll check it out, but I dont need anything big to keep me interested.

Kolkata.

So Chennai or Kochi? or is Kolkata worth the price premium ?

Kolkata.

Is there another airport with international flights I am missing?

Ahmedabad, Amritsar, Bagdogra, Bengaluru, Calicut, Chennai, Chandigarh, Cochin, Coimbatore, Delhi, Gaya, Goa, Guwahati, Hyderabad, Jaipur, Kolkata, Lucknow, Mangalore, Mumbai, Nagpur, Pune, Tiruchirapalli, Trivandrum, Varanasi & Vishakhapatnam

Of those, Varanasi is the other obvious contender.

Chennai --
Kolkatta +-
Kochi (if you follow LS's apt comment) ++
Bengalaru --
Hyderabad (if you research it beforehand)++ I stayed near a branch of Paradise restaurant:).
Chandigarh--
Mangalore+
Jaipur+
Goa +-
Mumbaii--
Vizag + but only if you go the tribal areas, hard to do in 2-3 days.
Pune + too big now but my home ground.
Varanasi - looks old but isn't.
Nagpur--
Trivandrum - good only if you are going to the development institute..

Another vote for Kolkata or Kochi. I like them both. The interesting part of Kochi is quite small and definitely feels different from the average Indian city, and is worth the visit. Kolkata is a large city and has some interesting sights, and a good food scene, especially sweets and the like.

There are some other airports with a handful of international flights. Not sure if you can include any of them in your plan but I really like Pune - a pleasant city with a quite nice, walkable centre. A few historical sights in the city lus several forts an easy day trip away.

Out of the places you mentioned Kolkata is most interesting if you like big cities. If you want a more relaxing stop in a seaside town where you can walk most places, go for Kochi, and head for Fort Cochin.

I haven't been to all of them.

But I liked Kolkata very much.Very,very interesting city.

If you do end up in Kolkata and have a few extra days in hand, take the train to Bolpur and spend some time in Santiniketan.

I also really enjoyed Calcutta, in fact I went back and visited it a second time when I was in India. From your description of what you like in an Indian city, I think the Calcutta will appeal to you a lot. It's a huge, sprawling city, with tons to see, so you can only really scratch the surface in 2-3 days.

Cochin's really enjoyable as well. The older part of town is separated from the new town by the backwaters, which I imagine has limited development there. Lots of nice historic sights, and, at least when I visited, more of a large village atmosphere than that of a city. There are lots of lovely daytrips you can do in the region around Cochin, enjoying the backwaters and some obscure historical sights scattered here and there. Cochin isn't very urban.

Madras is another massive city. It's less interesting than Calcutta, but you certainly won't run out of things to do in 2-3 days. Altogether though, the city has less atmosphere than Calcutta, and isn't as fun to just wander around. The old British fort there is top class though.

Cochin is very nice and it's an easy place to be--the rather touristy old city, as well as other older areas. I thought the backwaters were too touristy. You will find English is more common there than in Kolkata. That said, you can see alot if your based in central Kolkata--it's a relatively neglected city relative to Delhi, Mumbai, and Chennai which, ins some ways makes it more interesting. A lot of colonial history.

Alright good to know.

I'm also seeing I can get flights to Lucknow, which seems really interesting but the routing and timing is far less than ideal.

Kolkata definitely seems to be the clear favorite, and all things being equal I would choose it. Still not sure if I want to spring for the extra money for the flight and the less comfortable routing.

If not I'm left with Kochi or Chennai. Guess I need to do more reading. Thanks!