Maximizing Miles in the Maldives: Cathay First, Eating in Singapore, and a Park Hyatt Water Villa – American’s Chicago Flagship Lounge and the Final Journey Home

  1. Introduction
  2. Positioning flights to San Francisco, Sheraton Fisherman’s Wharf, and Some Dim Sum for the Day
  3. Cathay’s New San Francisco Lounge
  4. Cathay Pacific First Class, San Francisco – Hong Kong
  5. The Wing and Cathay Pacific First Class, Hong Kong – Singapore
  6. A Grand Suite at the Grand Hyatt Singapore
  7. Eating in Singapore
  8. Dinner at Waku Ghin, Marina Bay Sands
  9. Singapore Airlines Business Class: Singapore – Male
  10. Transfer to the Park Hyatt Hadahaa, Maldives
  11. Park Hyatt Maldives – Part I
  12. Park Hyatt Maldives – Part II
  13. Park Hyatt Maldives – Part III
  14. Maldivian, Kaadehdhoo – Male
  15. Singapore Airlines Business Class, Male – Singapore
  16. Cathay Pacific Business Class, Singapore – Hong Kong
  17. Conrad Hong Kong
  18. Cathay Pacific First Class, Hong Kong – Chicago
  19. American’s Chicago Flagship Lounge and the Final Journey Home

Off the flight and to the immigration hall, pick up the bags and walk them through customs, only to drop them back off.

The U.S. is exceedingly backwards compared to the rest of the world when it comes to connecting off of an international flight. I can see why non-citizens especially, but anyone traveling between two points that aren’t the U.S., wouldn’t want to connect here.

In Singapore you get off the plane, you go to your next flight, there’s security at the gate and that’s it. There’s no reason to claim your bags, no reason to go through Singapore immigration or customs if you aren’t entering Singapore.

In Thailand, if you’re connecting to one of the major domestic destinations, you proceed through transit immigration but you don’t clear customs until you arrive there.

Just connecting in the U.S. and not a citizen or permanent resident? At a minimum you’ll need the Visa-that-isn’t-a-Visa (“Visa waiver that you now even have to pay for”). And go through the bureaucratic hassle, hoping to make your connecting flight.

Once through the formalities, I took the train over to the American Airlines terminal, proceeded to clear security, and then headed off to the Flagship Lounge. I admit I probably should have just gone to the Admiral’s Club. I could have taken a much-needed shower there. But I hadn’t ever visited the Flagship Lounge in Chicago, and as an arriving international first class passenger witih oneworld and separately as an Executive Platinum on an international itinerary, I was entitled to access. I wanted to check it out, so I made the trek all the way down to gate K19 where it’s situated.

It’s just a lounge, with especially friendly and helpful agents and food, that you don’t have to pay for. And mid-shelf alcohol. But no showers. I get space constraints, and that the lounge is situated near many of the international departures, but coming off of a long haul international flight I would have loved to shower. But my desire to visit a new lounge trumped.

I still could have managed that shower with a return to the Admiral’s Club, though, because weather was worsening in Chicago and my Eagle flight home to DC was still sitting on the ground in Houston. But I was pretty tired as well, I sat down and tried to keep my eyes open while catching up on work, it was the end of the business week and I thought I could get myself close to in order and then spend the weekend catching up on personal stuff, recouping from jetlag, and doing the wash.

The flight appeared to be about an hour delayed. The agents in the lounge let me know when the arriving aircraft was due in, and I checked back at the desk around that time, they let me know that it had landed but wasn’t yet over to the gate. That’s when I decided to head over, recognizing that it could be better than a 10 minute walk over to Eagle.

Once I arrived at the gate I discovered that we were even a bit more delayed, while passengers were getting off we were also waiting on crew.

About an hour and a half behind schedule we boarded, most of the first class cabin was American crew, several of them new, and they were talking about their first flights, their schedules, the bidding process, and where they were commuting from.

The flight was choppy as could be, and what should have been an hour and a half turned into a bit longer as we circled on approach.

It was otherwise uneventful, though, and we were back home after a tremendously long trip back from the Maldives.

The next time, for sure, I’ll make the trip in a much less circuitous fashion. I love Singapore, mostly for the eating, but there’s not really a need to combine it with Central Asia. It’s one thing to do it as a stopover, and add on a short regional flight. It’s another thing to travel back from Central Asia via the Pacific. And via Singapore and Hong Kong no less, but then the Maldives isn’t the most accessible. I’ll burn far more American miles instead to fly Etihad via Abu Dhabi, though the connections aren’t the greatest.

I do think my two most recent Asia trips — in particular, stays at the Conrad Koh Samui and at the Park Hyatt Maldives — represent two of the very best point redemption values when looking for aspirational stays. The former because the base room type is a standalone ocean villa with its own pool, so a base room on points is fine (and a great value per point as well). The latter because the top Hyatt category offers real leverage at the top end, it’s no more points for the Park Hyatts in Paris and the Maldives than it is for the Grand Hyatt in New York. And the Park Hyatt is certainly a special resort.

Add in Cathay Pacific first class — very available on points redemption, an excellent seat, an overall reliable product — and how can you go wrong?

Writing this post already has me thinking about my next trip to the Maldives just as writing my last one had me thinking about booking a return to Asia even before I made this one. So there will certainly be more trip reports in this blogger’s future!

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

More articles by Gary Leff »



  1. Gary,

    Thank you for the trip report and all you do. Since I discovered your blog last year, I have converted to the free travel cause. I stayed at PH Vendome last year, 4 nights by doubling up on the chase hyatt cards, 1 for me and 1 for my wife. I called the chase reconsideration line this morning and it took them 3 times to three way in my wife, but we got it all straightened out and now her 50K sapphire card is in the mail. I’ll hit the spend req in the next week or so and will focus all expenses on her card. We already have 50K hyatt points, so with my sapphire + wife’s, I’ll be closing in on 150K points that could be used in the Maldives or back in Paris. We live on Oahu, so I’m not sure I need to burn points in the Maldives, but I really enjoyed your in depth blow by blow.

    FYI, we are headed for NYC and DC for a couple weeks in late June/July, and thanks to you, I’m feeling really good about this trip. Airfare for 2 adults and 2 kids (plus one infant) HNL-JFK is booked on HA for $900 all in roundtrip (212 one way and 70K points coming back). Staying at Westin Times Sq for 48K points for 5 nights….we’ll be gone 14 nights, all points or reward/anniversary certs– all thanks to you.

    Long Live Gary!

  2. Hi. Link #18 isn’t working Hong Kong to Chicago. Looking forward to reading that part of the trip report!

  3. Hey Gary, great stuff. I never even knew about the Maldives before this. I was trying to find how long was your vacation and how long did you stay in the Maldives? What would you say is the shortest amount one should stay there and would be worth it?

  4. My son and his bride just got back from the Maldives last week. He says the dirty little secret about the Maldives is the .

  5. @Ryan from MA – I stayed in the Maldives 5 nights, next time I will do 6, I can’t imagine doing less than 3-4.

  6. You didn’t miss anything at the Admirals’ Club in K. I went there last time I was in ORD, on one of the free invites that AA sent out as a courtesy.

    My visit – complete with free ice water and salty snack mix – convinced me that, if I’m ever going to pay for a lounge, it’s not going to be Admirals Clubs.

    But yes, there were showers.

  7. Some thoughts on the immigration thing. Not all US airports are set up to handle immigration – the US has many more airports than any other country. Also, most air travel in the US is domestic. As for security at the gate, do you ever fly through Kansas City or do they no longer have security at every gate? I get the problem of transiting through the US to another country – I would avoid that as well.

  8. Gary, while you’re dreaming about your next Maldives trip, dream of the new Park Hyatt I’ve been told is opening nearer to Male. I heard this from the PH employee in Male, who had confirmed it with Pierre Lang, the PH Maldives GM.

  9. Thanks for sharing your trip report with all the activities done by you. I loved the pictures, especially yummy food….. I was trying to find how long did you stay in the Maldives? It’s really interesting to hear.

Comments are closed.