Using Citi's 4th Night Free to Book a Cheaper Flight

We're big fans of the Citi Prestige's 4th Night Free benefit. That perk allows you to get 25% off your first four nights of any hotel stay four nights or longer. 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. Here's how that worked...

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 extra money in an Uber or cab. Basically, $168 per person on the United flight or the later Southwest flight 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 on

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)

  • 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!

We 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.

Closing Thoughts

Being realistic about your schedule is one of our top tips on how to save on your Disney vacation. Travel takes time, especially with a family. 4th Night Free isn't a perk that looks like it would be a way to save money on flights, but sometimes tinkering with your schedule works out. In this case, we got more Disney for less money, and that's a win.