Allrighty, this might deserve to go into the credit card forum, so please feel free to move if necessary! ***

Boyfriend and I are looking to check out the new Hyatt Papagayo in May of next year. I have two free nights through my Chase Hyatt card, as well as 40k immediate Hyatt Gold Passport points coming through in the next two months. I plan to get an additional 4k points (or transfer from Chase UR) to get us 4 nights.

Ideas for flights? Airline? Signup bonus? We would be flying out of Indianapolis (if necessary, Chicago).

Below are our credit cards each. Boyfriend plans to buy a new car in February, so inquiries will not be his friend right now I assume...

Me: Chase Hyatt, CSP (51k points now), Freedom, and BCP. Last app was in July.

BF: CSP and Freedom

If you can start within 524 miles of IAH, you can get 2 seats on United with 22K ANA miles per person, transferred from AMEX (One signup bonus for BRG gets 2 tickets) or SPG. Using Avios on AA, MIA-LIR is 7500 Avios, DFW-LIR is 10K. Use AMEX BRG for those as well. If you're not in the South or Southeast, that is also off-peak time for AA at 30K RT. http://www.flyertalk.com/forum/credi...ost-first.html

Edit: AA will be your best bet from IND or ORD if you can find workable dates.

For five days in May AA would be the best at 30k RT! That is great! When is the best time to apply for the Citi AA and SPG? I would need to apply for both to get the bonuses. Assume waiting six months after recent apps?

Hyatt-6/13
CSP-5/13
BCP-6/13
Freedom-11/12

Luckily the SPG will only be a soft pull if declined, but should not be an issue. CS around 760.

The last 2 cards I got were Citi AA and SPG, score similar to yours, they were cards 15 and 16 approved in 2013. Same for my wife except they were 13 and 14 for her. You are golden, the best time to apply is tomorrow morning for both if you can meet the spending requirements. AMEX BRG plus AA is also a possibility; you can book 2 one-ways with AA at 15K each and 2 with BA at 17,500 each.

A little warning: AMEX cookies can screw up applications, so use a private browser for any AMEX application. Actually, use a private browser for all apps, always.

Thanks for the insight with the cookies! I have to do this when going through UR Mall too... :/

As far as PRG, no issue with applying as "sole proprietor" although we do not own our own business? I know I apply with my SSN, just curious how strict AMEX is with this.

If I could meet the spending requirements in 3 months, do you think it's okay to wait until December or would you advise against? The last thing I want is them telling me I'm searching for too much credit too recently.

Question - regarding the comment above stating that MIA - LIR is 7,500 AVIOS, I get the message below. Is there a workaround or another method to book to LIR via Avios?

Sorry, we do not currently fly to your chosen destination.

Please select an alternative destination below, or start again.

(Distance from your original airport choice is shown in brackets)

San Jose (Costa Rica), Costa Rica, SJO, San Jose (Costa Rica) (161km)
Managua, Nicaragua, MGA, Managua (185km)

No LIR booking online - bizarre. They should be able to book it over the phone.

Just an aside, expect to be held up for a "departure tax" by airport officials upon trying to enter the check-in line and depart San Jose and probably LIR also. If you use a credit card they will knick it as a cash advance (but not tell you).

You are obviously a lot more patient than me. Any time should be fine, but there are no guarantees of available seats.

In our experience and from everything I have seen and heard about it, BRG is easy to get, with no questions about the business.

Related to the Costa Rica Departure Tax out of SJO and LIR, keep in mind that many hotels catering to tourists in the region have the ability to process your departure tax and print your form on-site. Thus, you will not have to wait in line at the airport on day of departure.

Just have your passport handy and ask the hotel front desk receptionist or concierge.

I did that twice with my Hilton hotel in San Jose and it can be charged to your room(more Hilton points). All you need is your passport and they will give a receipt with departure tax paid which you need to show to check-in agent.

I believe only flights to SJO can be booked online, so go to aa.com to see what MileSAAver seats are available. When you find a flight you want, call BA to book it and ask if they will waive the phone fee because you were not able to book this online. (I have no clue if they will waive the fee or not.)

Any idea if the Radisson in San Jose will do it?

I booked a ticket out of LIR online a few months ago. It's an AA flight.