How We Used Citi's 4th Night To Allow Us to Book a Cheaper Flight and Get More Disney

We've written a lot about the Citi Prestige's 4th Night Free benefit. For those of you not familiar, it essentially works like this:

  1. You contact the Citi concierge to book a hotel stay, including at Disney hotels, of at least 4 nights.
  2. You pay with your Citi Prestige
  3. Once your stay is paid for in full (either at the time of booking, or when you check out of the hotel), you'll receive a refund on your card in the amount of the cost of the 4th night within 1-2 billing cycles (after July 23 the amount will be based on your average nightly stay and won't include taxes).

We previously used the 4th Night Free to save on two nights in a single Walt Disney World stay by splitting our nine nights across two resorts.

Our two 4th Night Free credits from our trip ending early January.

Our two 4th Night Free credits from our trip ending early January.

This past weekend we used 4th Night Free for another purpose - to save on flights.

Our Flight Options

I'm a bit of a nutcase when it comes to booking flights, so I won't go into all the details and if-thens I went through booking our flight. Suffice to say I was looking to book a nonstop flight from Chicago to Orlando in early July. I wanted to get in early to have a full Disney day. According to Google flights, my options were:

Google flights doesn't search Southwest, so I had to pull up those fares separately.

Now, because of my particular life circumstances, I can get to O'Hare (ORD) for an early flight no problem. Getting to Midway (MDW) early would probably cost be extra money in an Uber or cab. Basically, $168 per person was my best option.

Enter 4th Night Free

These are not awful options that we're left with, but then I thought of one of the tricks I'd wanted to try. We were only planning to stay three nights and had no obvious way to make real use of a fourth. It's rare, but we've planned trips before where getting an extra hotel night after arriving late one day early was cheaper than other flight options. In this case, with 4th Night Free, the extra night was free. So I looked at flights the day before and found this gem:

We'll be booking at the $110 rate.

We'll be booking at the $110 rate.

I love this flight for a lot of reasons. It's Southwest, which means I don't have to worry about bringing a carry-on. It departs at a decent time (so we can take the train to the airport), and it gets in at a decent time where we'll be able to get to bed at a reasonable hour and then have an entire next day of Disney!

Em called the Citi Concierge to book our stay for four nights, and we're set! We're basically using 4th Night Free to save $100 on flights and make sure we have a full day of Disney on our first day.