Q. Living on the west coast, I usually have to fly to New York before I head to Europe. I love New York and would like to stay over for three or four days. Are there any airlines that would allow me to "layover" for a couple of days, retrieve my luggage, then re-check it when I'm ready to continue and do all this at a reasonable round-trip price, or should I just book two separate trips?
A. While stopover arrangements like this certainly aren't unheard of (Air New Zealand often allows for stopovers in the Cook Islands, Cathay Pacific sometimes allows stops in Hong Kong, Icelandair often runs free stopover deals in Reykjavik for Euro-bound passengers...), it's not something we see much of from American carriers, and especially when we're talking about domestic stopovers. Well, unless you graciously choose to count sleeping overnight on the floor at O'Hare as a "domestic stopover" rather than a cancelled flight. Shop around. Try searching multi-city itineraries on a few booking sites and see if you can beat the cost of booking two separate trips.