A FlyerTalk Posting Legend
Join Date: Jul 2002
Location: MCI
Programs: AA Gold 1MM, AS MVP, UA Silver, WN A-List, Marriott LT Titanium, HH Diamond
Posts: 53,006
Finding regular coach award availability to Europe is not easy. I'm not saying these juicy credit card bonuses aren't great deals, but be prepared for those miles to be useless for this particular trip.
Most of my travel experiences have been with MCI as my home airport and there have only been one or two itineraries in my life where I recall saving a few hundred dollars by buying a separate ticket to Chicago. More often than not, MCI is competitive enough on flights to Europe that the extra time/risk/hassle associated with two itineraries isn't justified.
But maybe Ukrainian carrier out of NYC has rock-bottom fares. Or maybe LOT out of Chicago has a deal to Warsaw that no one is matching from other cities. In any case, if you decide to go this route, seriously consider spending one night in Chicago or NYC.
If a delay on the Southwest flight causes you to miss the international flight, that 2nd airline doesn't really owe you anything. They'll probably put you on a standby list for the next day but who knows whether that'll lead to a seat in the middle of June? If your cheap Ukraine flight departs JFK on a Wednesday night, then fly into Newark midafternoon Tuesday and enjoy Manhattan for a day.
If you're really pinched for time, or if Chicago or NYC hold no interest to you at all, then just book one ticket on a major alliance and perhaps price-shop on the European end to find a cheaper city in which to arrive.
For summer travel in the past, we've often bought MCI-MUC as our main ticket and then either used a short-hop award or rented a car out of there. But we've never gone quite as far east as you're talking...