Travelling from LAX, wants to go chicago, connecticut and boston

Hi guys,

my sister is getting married in august and the wedding is happening in connecticut near new york. we are travelling from LAX. however we want to visit chicago and boston aside from connecticut.

what should our itinerary be

LAX - > Chicago (3 days) - > Connecticut -> drive to Boston (3 days) and drive back to Connecticut to flyout from there back to LAX.

is this the best way to save money? its going to be for 4 people.

should we do the chicago after the trip? will it be cheaper?

i figure 2 one way tickets from lax to chicago and chi to connecticut is going to cost a lot. is there a way we can buy tickets from LAX to CT roundtrip but with a 3 day stopover at chicago?

i just want to know the best and most cost efficient way. and no, we wont drive from chicago to CT. i think its too far haha

thanks!