Earlier this year, we enjoyed a trip to Tokyo, Japan for nine days and eight nights. My wife, mother and I flew round-trip with just one connection, and stayed in the heart of Tokyo’s business district at a 4.5 star hotel in Shinjuku. We stayed on the executive floor and enjoyed access to the Executive Lounge offering breakfast, snacks and cocktails; and we did it all for less than $237/person.


Service Value Paid
Hotel – 8 nights w/ Exec Lounge $4,861 $95
Round-trip Airfare for 3 $4,129 $615
Sum $8,990 $710 (92% off!)
$236.67 / person

The $710 paid was a result of taxes incurred, and annual fees associated with credit cards we acquired solely for this trip.


It pays to use points for airfare and hotel expenses because not only are the exchange rates favorable, you typically aren’t charged the same high taxes and fees. In the screenshot below, you can see Hilton charges nearly $900 USD for what it calls “Taxes” and a “Service Charge” on this eight-night stay.


Using 50,000 Alaska Airlines miles each, we redeemed our mileage through the Airline Partners program. This is the lowest round-trip redemption available so you’ll need to be flexible with your travel dates to ensure you’re redeeming the best value. The fees on this redemption are listed, and are your only costs incurred on the transaction. They vary by itinerary, but for the example below, would run you $82/person.

Mileage Redemption

Flexibility is key when booking travel because some days will not have the best redemption values available.


Again, flexibility is the name of the game. In fact, despite booking this same hotel for 50,000 points / night for these dates a year ago, the asking value is currently triple what we paid. For that reason, you must be fluid with your planning in order to find the best value for your points. We selected the Hilton Tokyo at the time because of its value offered, but also because Hilton offers a 5th night free promotion for point redemption; effectively allowing you to take 20% off a 5 or 10 night stay.


Hilton Tokyo

Our room included a beautiful city view, traditional shoji screen and fusuma, and accommodated an additional twin bed.

Hilton Gold

Automatically earned when you’re carrying American Express’ Hilton Surpass card or Platinum card, Gold status is what prioritizes you for a room on the Executive Floors. This is valuable, especially at this property, because you’re granted access to the Executive Lounge which happens to be a light-fares restaurant on the top of the high-rise hotel. Complete with a full breakfast in the morning, hors d’oeuvres throughout the day and a full bar at night, this complimentary service will not only enhance your trip, but save you money.

Executive Lounge

The executive lounge boasted a fresh omelette chef to round out each morning’s breakfast.

Collecting Your Points

When you’re planning a massive point redemption like we did, it’s never too early to start accumulating the right points and miles. As you do this, be mindful of terms and conditions associated with earning and using your rewards. For instance, American Express strictly enforces its “once per lifetime” rule that stipulates you can only earn each of their promotions once in your lifetime. However, Hilton recently offered the ability to pool points with friends and family at no-charge so this can be an effective way to combine signup bonuses.

Cards to Consider

I am never compensated for my recommendations. But for your reference, here are some of the cards we found helpful to collect when planning this trip:

  • Hilton Aspire Card from American Express (link)
  • Citi ThankYou Premier Card (link)
  • Alaska Airlines Visa Signature Card (link)

We were also able to take advantage of two Hilton cards offered by Citi bank, but due to a new exclusivity deal between Hilton and American Express, those cards are no longer available.

In Conclusion

When planning a trip this large, you’ll only be successful if you can stay adaptable and book with the properties/airlines offering the best deal on the dates they stipulate. It can be a daunting treasure hunt, but the rewards are plentiful. Happy travels!