Originally Posted by gfunkdave

If you want guaranteed warmer than 60s, San Diego or Miami or maybe even New Orleans.

I just got back from a long weekend in Bermuda and it was perfect. Not officially the US, but it might as well be. Almost all the flights from BDA are to the US, the electrical outlets are the same, their cable TV system even has all the same TV channels as you'd find here (including network affiliates from Miami). Everything's easy (albeit a little expensive). There are some things to do (neat caves, walk around Hamilton, which is actually kinda cute, etc) as well as good restaurants, beaches, golf, tennis. US customs preclearance back to the US. It was mid 60s our first couple days then mid/upper 70s after. It's just about never below about 55 or above 90. You can stay at one of the Fairmont properties if you want to be fancy. We stayed at The Reefs, which felt like it was the nicest resort on the island before the big brands came in.

No nonstops from ORD, unfortunately, but on AA you could stop in PHL or CLT. It's a quick flight to Bermuda...only 90 mins from JFK and probably a little less than that from CLT.