Missing a connection on purpose?
 

I'm trying to book a rewards flight to Italy. In order to get the cheapest flight, I would need to fly out of Hartford, CT to Venice. There is one connection, I am fine with this part. On the way home we would fly out of Rome to Hartford. The issue is with the connection on the way home. It connects in NYC and there is a 7 hour layover. If I try and book the flight to come back and stop in NYC, it is significantly more expensive and I don't have enough points. Can I just miss the last leg of the trip since NYC is actually a bit closer to where I live?

Generally you can. Techinically the airlines can "penalize" you and charge you for this type of things... but in truth they only do that if you make a habit of it. Now if you check luggage that's an issue because it will be checked to Hartford.....

My parents live about 40 minutes from Hartford, they can pick it up, but what happens with customs?

If NYC is your entry point into the USA, you should have to collect your bags and go through customs and immigration there. Just hang on to your bags and walk out the door. I've done that before (at ORD, rather than taking a commuter flt onward) and UA never said anything. I do not make it a regular practice; I've only done it once or twice in many years of flying with UA.

Doable have done it but wiser to

arrange RT NYC so as not to raise

carrier/customs eyebrows.

Not strictly per your contract of carriage.

Customs doesn't give a flip about your final destination or connecting flight plans. Their only concern is what goods you are bringing into the US.

If you plan to stay in NY and not get the connecting flight, then remove your baggage tags BEFORE you exit customs. There are sometimes "helpful" airline personnel who look at baggage tags and "help" you find your way to the baggage re-check counter.

Thanks for all of your replies. The prices dropped over the weekend so we ended up finding flights that worked much better for us flying out of an airport about 10 minutes from where we live and we won't have to deal with long layovers.