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As you read this, I’m 35,000 feet up on my way to Medellin, Colombia.

I was in Tucson over the weekend for a tennis tournament, and I didn’t have any exit flight booked. I really wanted to return to Colombia because I had enjoyed Bogota so much and heard even better things about Medellin, but award space didn’t appear to be available for a Monday departure from Tucson to Medellin.

I used two tricks and a little bit of creativity to come up with a Saver award, save myself $75 in fees, and give myself a chance to hang out with a buddy I haven’t seen in a few years.

• What were my two tricks?
• How did I save $75?

1. Segment-by-Segment Searching

Segment-by-segment searching is less a “trick” and more “the way you should do most searches that don’t yield immediate award space.”

I searched for award space from Tucson to Medellin on all conceivable airlines. Here’s what a search for November 17 brought up on united.com: nothing!

So I started searching segment-by-segment. I knew if I could get to Houston and overnight there, I might have more options in the morning.

On a one way United award, you can’t have any stopovers, but layovers less than 24 hours are fine on international awards.

On November 17, I found this flight with economy award space. It would get me in at 8:05 PM to Houston.

The next morning I could fly Houston to Panama to Medellin and arrive in the afternoon. I didn’t want to arrive in the middle of the night like many of the flights to Medellin do.

This itinerary looked perfect for me. It would allow me to run some errands in the morning in Tucson, spend an evening in Houston with my good friend, and head back to the airport the next morning to get to Medellin by mid-afternoon.

I noted the cabin, flight number, and date of each flight, but I didn’t book yet.

2. Avoiding the $75 Fee for Booking United Flights within 21 Days of Departure

I booked my flights about three days before departure. Any United award booked within 21 days of departure incurs a $75 close-in ticketing fee (reduced or eliminated if you have status.)

I explained in this post how to get around that fee: Don’t Pay the $75 Close In Fee on United (Trick!)

The gist is to book an award from your departure city to your destination for a distant future date then call United to change to your real date. Changes and cancellations within 24 hours of booking an award are free.

I booked an award for January for 20,000 miles and $26.70.

Then I immediately called up United at 800-UNITED-1. I let the agent know I wanted to change my dates, and I had my flights picked out. I gave her the dates, cabins, and flight numbers.

She had no trouble piecing together the award. She let me know that I was covered by the rule allowing free changes within 24 hours of booking. My actual award had taxes $0.75 higher than my originally booked award, so she got my credit card number to make that charge.

I have double-checked, and my credit card only shows two charges from United, totaling the taxes of $27.45. I have not been charged $75 for booking my award within 21 days of departure.

Bottom Line

I’m ecstatic with my itinerary. There is no way to get from Tucson to Medellin with fewer than two stops. At least I’m maximizing my itinerary to hang out with a buddy along the way, get in to Medellin at a reasonable hour, and minimize the cash I spent on my ticket.

Watch out, Medellin!