Hello,
Acquiring Transit visa is a VISA process all together.
Most of the times you can confirm on the web page itself, if that particular route needs a transit visa. For Indians, if you got to makemytrip and try and book a flight, on filling in the details and BEFORE payment you give in your phone number , within seconds you will get a call from their travel agency and you have a word with them to clarify your doubts.
Now, Chicago is in the US and yes that needs a TV.It will cost you 32,000 INR and takes 20 working days to process.
I too am from Hyderabad. Ive booked a flight that goes through London.
Hyderabad->London->Toronto . No Transit visa required for this route.