cpaynter

I'm looking for the best way to get from Chicago to Dominica for about two weeks in February 2016. I'm open to using cash and/or miles; mainly looking for the best combination and best time to buy. I'm particularly interested if anyone has creative ideas for leveraging miles and points.

Dominica can be tricky; there are very few flights in, and AFAIK, none from mainland US. All seem to require flying first to another Caribbean airport (e.g. SJU), then a puddle jumper (Seaborne or LIAT) to DOM. From Chicago, many itineraries also end up requiring an overnight stay either in MIA or SJU. From a time, hassle and hotel-cost standpoint, we prefer the non-overnight option.

When we last flew to Dominica in 2012, it was great; American was offering awards flights for the entire flight (ORD->MIA->SJU on American, SJU->DOM on American Eagle and reverse on the way back), so the trip cost us $15 each. But it appears that nobody is offering awards flights now. American offers flight combinations (using Seaborne for the DOM section), but not using awards.

JetBlue also sells complete ORD->DOM itineraries (using Seaborne), but doesn't allow booking out that far in the future yet.

I've been fairly good at collecting miles and points, less successful at optimally redeeming them. Here's what I have banked:

American Air 91K (me) 114k (DW)
United 93K (me) 72K (DW)
Chase URP 140k
USBank FlexPerks 49k

Current options we're looking at:

1. Cash - Google Flights is showing same-day flights (using American and Seaborne) for $820 each.

2. USBank FlexPerks - They're offering same-day flights using American & Seaborne for 40k points. Since we only have 49k points banked, we'd have to buy an additional 31k points for $620. Over the next couple of months we'll continue to accumulate a few thousand more points which would reduce the number we'd have to buy, but of course, the longer we wait the greater chance that the 40k flights will go away.

3. Use AA awards miles (35k each economy RT or 60k each business/first RT) to fly ORD->SJU, then pay ~$430 cash each RT for a Seaborne flight from SJU->DOM.

4. Wait for JetBlue to open up their booking window for this time period (likely sometime in June). The JetBlue option has an advantage in that our first-bag-each-free on JetBlue should carry over to Seaborne so we wouldn't have to pay luggage fees to Seaborne.

I'd love to be able to transfer my URP to OneWorld and book there using miles, but Dominica doesn't seem to be a valid destination for the OneWorld booker.

So to reiterate my main questions:

1. Am I missing any options here?
2. Should I jump on this now, or wait a while to see if better options arise?

TIA for any suggestions.

Chris.