When Two Free Nights Will Cost You More Than One Free Night At The Same Property

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Friends of ours will be visiting Los Angeles in December and they asked if I would give them some advice on booking their trip and help them out with their accommodation. Naturally I said yes and I started exploring a few options on their behalf….but things didn’t quite turn out as I expected them to turn out.

Here’s the basic info on the trip:

  • They’ll be traveling as a 3-person family
  • They’d like to stay in LA for 7 – 10 days (depending on accommodation costs)
  • They have a little over 50,000 World of Hyatt Points, and two small balances of IHG Rewards points.
  • One of them holds the Citi Prestige credit card

The thought that immediately went through my mind when I looked at the trip info was that the Andaz West Hollywood would suit them very well.

The location is perfect for people who like to explore on foot, there are plenty of eateries around, the rooms are good and they could use their Hyatt points to upgrade to an Andaz King suite which would give them all a lot more room.

a room with a large window and a chair

The Best Western (across the road from the Andaz) may be a good option too as, perhaps, would be the Grafton just a little further west on Sunset.

It also occurred to me that this could be a very good trip on which to really maximize the value of their Citi Prestige card which offers a 4th night free on stays of 4 nights or more when booking through the Citi Concierge/Citi website.

Now, before I continue it’s going to be important to remember that there are two big limitations to the Citi Prestige’s 4th night free benefit:

  1. You only get one free night per stay regardless of how long the stay is.
  2. Back to back stays (4 nights + another 4 nights) will still count as a single stay and will only qualify for a single fee night.

Still, I figured that this could be an opportunity to get creative and an opportunity to attempt to circumvent these limitations to see what is actually possible – I love a challenge!

This is what I wanted to try:

  • Book a 4-night stay in the name of guest 1 using the Citi Concierge and the Citi Prestige Card
  • Follow this with a 1-night stay at the same property booked in the name of guest 2 using any card other than the Citi Prestige
  • Follow the 1-night stay with a second 4-night stay booked in the name of guest 1 using the Citi Concierge and the Citi Prestige Card

This would give them a total of 9 nights in LA with 2 of those nights being rebated by the Citi Prestige card and, at check-in, they could explain that the three reservations were all theirs and the front desk would ensure that they didn’t have to move rooms part way through their stay.

a city skyline with trees and buildings

In theory this sounded like a nice way to get these guys 2 free nights, to keep their trip costs low and allow them to have a longer trip.

What I found out next really surprised me.

I priced up three 9-night trips for separate sets of dates around the time our friends want to visit. For each set of dates I checked the cost of booking the 9 nights as two 4-nights stays and a 1-night stay (to maximize the Citi Prestige 4th night free benefit) and the cost of booking the same 9 nights in one block (and only getting one free night through Citi).

This is what the results looked like (click image to enlarge):

a graph with numbers and a number on it

In all three cases it was considerably cheaper to book the nights in one single block (and to get just one free night) than it was to try to game the Citi Prestige benefit and get two free nights.

Not only was I surprised at the result but I was also surprised by how much cheaper the single block booking was on each occasion – with one difference being almost $500 it wasn’t even close!

Bottom Line

I’ve always known that hotel prices can be cheaper when multiple nights are booked (this doesn’t always hold to be true) but I never realised just how much cheaper the longer bookings could be (on a per night basis).

In this instance, booking in a single block was between $40 and $55 cheaper per night than booking the same room in three separate blocks and, as you can see, that quickly adds up!

The moral of the story here is that you should never make assumptions when costing out a trip.

Logically one would assume that, for the same set of dates, a booking that earns two free nights would be cheaper than a booking which only earns one…but that’s very obviously not the case.

This may not apply to every occasion or to every property but this phenomenon is definitely worth bearing in mind the next time you’re trying to milk as many free nights out of your Citi Prestige card as possible (before the annual limit is introduced later this year) – two free nights is definitely not always cheaper than settling for just the one.


  1. Crazy how that works. The Citi prestige 4th night is nice, but not hard to beat with a little research. Depending on the taxes, it really only amounts to a 15-20% discount. I think when the concierge bookings become unavailable in September, the value will really drop. 2 prepaid bookings per year, for $250.

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