(Cancun, Mexico)

A TTM contributor received a $500 United Airlines certificate when United overbooked his flight (over the holidays) and rebooked him at the gate on a significantly less convenient flight.  Instead of taking the initial offer of a $300 United Airlines certificate, this savvy traveler negotiated a $500 United Airline certificate, $30 worth of food on the flight, and an upgrade to first class on the return trip.  I flew an American flight that was trapped in ORD until 3a on Christmas but I only received 8,000 miles for this inconvenience.  While his airline was certainly in a different position than mine, I still admire his negotiating skills.

Anyways, his $500 United Airlines certificate is about to expire so he asked for my assistance in assessing his options.  The TTM contributor has the following travel restrictions:

• He must fly out of ORD (Chicago, IL)
• He must fly on United- and United Express-operated flights or a United Express-marketed flights operated by other airlines (this greatly reduces the number of available destinations)
• He cannot spend more than $250ish more than his voucher
• His trip cannot last longer than a week
• He can only travel during the last two weeks of January and the first two weeks of February

5 Best options (in no particular order)

1. Honolulu, Hawaii ($742): he could book a trip to Honolulu that leaves on February 2nd and departs on February 9th.  This flight has two short layovers in LAX and SFO.  Chicago to Los Angeles is operated by United’s fairly new Boeing 737-900.
2. Rio de Janiero, Brazil ($744): this trip leaves on January 19th and departs on the 25th, with a short layover in United’s Houston hub.  The Houston to Rio de Janiero route is operated by United’s fairly new Boeing 787’s.
3. Cancun, Mexico – Business Class ($708): this non-stop flight leaves January 25th and departs on the February 2nd.  He has the option to schedule up to a 10 hour layover in Houston for only a few extra dollars.  The non-stop flight is operated by United’s fairly new Boeing 737-900.  While the seats on the 737-900 don’t lay flat, they’re still a solid business class option for a four hour flight.
4. Belfast, Ireland ($767): this trip leaves on January 21st and returns on January 28th, with an overnight layover in Newark, NJ (EWR).
5. Dublin, Ireland ($740): this trip leaves on January 21st and returns on January 28th, with a short layover in Newark, NJ (EWR).  This trip is fairly flexible and most dates in his time frame qualify.

 

Which option would you choose?