Coming out of the Closet

How can you afford it? Do you ever work? These are the two main questions I get asked by my friends when I tell them I just got back from another trip. In their minds I must have won the lottery and I am either retired or have unlimited vacation time. So, with all these questions floating around… I’ve decided to come out. I did not win the lottery, I am not rich, and definitely nobody is paying for my travels (any takers though?). I also have a full time job and I get about three weeks of vacation time per year. Yet last year I was fortunate enough to squeeze in a couple of ski trips to Utah, a couple of trips to Asia and the Middle East, as well as a few local trips in the States. How? Most of my international flights are paid with miles/points or I happen to find really cheap airfare. In the States, unless I find some really good deals, I almost exclusively fly Southwest – miles/points again. Hotels are usually covered by points or a combination of points+cash. In other words, flights and hotels typically don’t cost me much. When it comes to finding time for vacation, I tend to take many weekend trips in the States and short (3-4 days) trips internationally. Whenever possible, I try to combine national holidays to stretch my vacations.

Sheikh Zayed Mosque, Abu Dhabi

For example, my flight to Abu Dhabi cost me $220 all in, from Chicago to Abu Dhabi and back to Chicago. And there was even a free shuttle to Dubai for those who wanted to take a side trip (which I took advantage of). This is not the “normal” price for such a long flight, it’s typically much more expensive. Finding these types of deals is not rocket science, but you have to be alert and ready. Make sure to check online travel sites like The Flight Deal or AirfareWatchDog, sign up for their newsletters or follow them on Twitter. These sites do all of the work and notify you if there are any good deals, all you have to do is decide whether it’s worth going. It definitely helps if you are flexible with your travel dates and can act (buy the flights) quickly. I found this particular Abu Dhabi deal on The Flight Deal and shared it with my friends – quite a few were able to take advantage of it, but they made the purchase the same day (the deal was gone by the following morning). My hotels for this trip were completely covered by points (Hyatt points to be exact) – four nights at the hotel cost me zero dollars.

I know that not everyone has the flexibility or the desire to spend 13 hours in the middle seat surrounded by strangers. In that case, I would advise taking shorter trips (long weekends perhaps). Here is what works best from my experience: pack on Thursday, head to the airport straight after work on Friday and fly somewhere warm (bye Chicago winter!). Relax by the pool on Saturday/ Sunday and head back home on Sunday night. For example, the logistics of my weekend getaway to San Diego were covered by points – I used Southwest points + $11 for the round-trip flights and the hotel was completely covered by points, so it cost me zero dollars. Well, since this was a fancy hotel, a cocktail cost me $20, but that’s another story….

La Valencia Hotel

If paying $20 for a cocktail sounds too much, there are ways to get drinks for free – fly first class and enjoy a glass (or a bottle, no judgment here) of Krug. Alright, this may be an extreme example, but that’s the beauty of miles/points, you can travel in ways that would typically not be possible! My first class flight on Cathay Pacific from Chicago to Hong Kong was covered by miles, I just had to pay around $40 in taxes. The retail value of the flight was around $11,000, which I would never be able to afford. But thanks to miles/points, now I know what real champagne tastes like.

Cathay Pacific First Class

I am not trying to brag about my travels, that’s not my intention at all! But I do want to show that it is possible to travel without having a bunch of money in the bank. I think everyone can do it with a little bit of planning and the desire to explore. As they say, “if there’s a will, there’s a way.” Happy travels!