5 Nights in New York City Times Square For FREE

I spent 5 nights in New York City Times Square to celebrate New Year’s, spending $0 instead of $9,000.

5 nights in “Tempo by Hilton” during the busy Christmas/New-Years/Holiday period can cost up to $12,000, depending on the room. In our case, we booked a standard room with Hilton Honors points that would have otherwise cost $6,000.

We got upgraded upon check-in as well, but more on that later.

In this blog post, I will show you how I used credit cards to make this possible, and how you can do the same.

First, if you want to check out our trip photos, you can do so here (Spoiler Alert: the album also contains our Boston photos. I will write all about our Boston redemption next week).

Let’s get started.

5-Nights in Hilton Tempo Cash Value

We booked the standard rooms that were going for a total of $6,074 if we booked all 5 nights in cash.

Being Hilton Gold members (through Hilton Surpass card), we were upgraded to “times square view” rooms upon check-in.

The 5 nights cash price of the upgraded rooms was around $9,000.

In my wildest dreams I cannot see myself spending $9K for 5 nights, even if that means not staying in Times Square for our first NYC trip.

I mostly wanted to stay in Times Square to see the historic ball drop on the 31st. It was worth it! If I couldn’t make this happen without points, most likely I would have never experienced something so awesome.

Okay, so let’s see how I managed a $9,000 hotel stay for free using credit card points.

90,000 Hilton Honors Points Per Night

Being a Hilton Gold member (through Hilton Surpass card), I get three important benefits:

Stay 4 nights, get 5th night free.

Room upgrade upon check-in, if available

$35 daily food and beverage credit

Let me talk about (2) and (3) first, then (1).

I already mentioned (2) - we received a room upgrade upon check-in. The “times square view” room was beautiful!

We spent the $35 daily food and beverage credit on water, hot chocolate and coffee from the onsite restaurant.

Those benefits were amazing, but the biggest win came from the “stay 4 nights, get 5th night free” benefit. Let’s run some numbers.

Points Per Night = 90,000
Total Points for 5 Nights = 450,000
Total Points for 4 Nights = 360,000

Cash Value for 5 Nights (w/o upgrade) = $6,000
Cash Value for 5 Nights (w/ upgrade) = $9,000

Here are the cents-per-points (CPP) for the standard room.

CPP without 5th night free = 1.33 CPP
CPP with 5th night free = 1.7 CPP

Here are the cents-per-points (CPP) for the upgraded room.

CPP without 5th night free = 2 CPP
CPP with 5th night free = 2.5 CPP

I think it’s fair to say I scored 2.5 cents per Hilton Honors point for my 5-nights stay.

What Credit Cards I Used

There are 2 primary ways you can earn Hilton Honors points:

Use AMEX’s Hilton credit cards (Hilton Honors, Hilton Surpass, Hilton Aspire)

Use AMEX’s MR points earning cards (AMEX Gold, AMEX Green, AMEX Platinum)

When taking approach (1), you directly earn Hilton points in your Hilton account.

When taking approach (2), you can transfer your MR points to Hilton. Typically, 1MR point equals 2 Hilton points. However, during promotions (which happens 3-4 times annually), 1MR point equals 2.6 Hilton points.

1 MR Point = 2 Hilton Points (w/o bonus)
1 MR Point = 2.6 Hilton Points (w/ bonus)

Which approach did I take? A combination of (1) and (2).

Primarily, I used 3 credit cards:

Hilton Surpass Card - a sign-up bonus of 130K Hilton Points. Another 10K from spending on the card. So, total 140K Hilton Points

American Express Blue Business Plus - earned MR points to transfer to Hilton at 1:2.6

American Express Gold - earned MR points to transfer to Hilton at 1:2.6.

If you run the numbers:

140K Hilton Points from the Hilton Surpass Card

85K MR points transferred at 1:2.6 from American Express (earned through AMEX Gold & Blue Business Plus)

That’s a total of 360K Hilton Honors points that I needed to do the booking.

An Easier Approach You Can Take

If you are still reading, I think it’s fair to assume you want to do something similar.

You can take a much easier approach! I will give you the strategy for 5-nights, but if you want fewer nights, just execute part of the plan instead.

So, 5-nights at Hilton Tempo during New Year’s will cost you 360K Hilton Points.

Approach 1: Hilton Credit Cards

Get 3 Hilton credit cards, get the sign-up-bonuses, book your trip (with one extra night!).

Hilton Honors Card - 80K points

Hilton Surpass Card - 130K points

Hilton Aspire Card - 150K points (also gives you an annual free night)

That’s a total of 360K points, as well as a certificate you can use to turn it into a 6-night stay.

Approach 2: American Express

Get 1 American Express and 1 Hilton card, get the sign-up-bonuses, transfer the points, book your trip.

Hilton Surpass Card - 130K points

American Express Gold Card - (100K MR or 260K Hilton points)

Once you transfer your American Express MR points to Hilton at 1:2.6, you end up with 390K Hilton Honors points, more than enough to do the booking.

Approach 3: Slow Accumulation

If you don’t want to sign up for too many cards or don’t want the hassle of hitting minimum requirements for sign-up bonuses, you can do the following.

Pick the right credit cards for your setup

Spend on them to earn points

Eventually accumulate enough to book

In that case, I would recommend the same setup as approach 2.

Hilton Surpass Card - 6X Gas, 4X Retail Purchases, 3X Everything Else

American Express Gold - 4X Dining, 4X Groceries, 3X Flights

You also get 1 free night certificate when you spend $15K in a calendar year on the Hilton Surpass card.

If you regularly spend in the above 2 cards, you will earn points at a fast enough rate to get 360K points fairly quickly.

Summary

In short, using either 3 Hilton cards or a 2-card setup (1 Hilton, 1 American Express), you can earn 360,000 points which is enough for a 5-nights stay in Hilton Tempo during busy holiday season.