Despite doing my current Americas focussed job with Amadeus for quite a few months, it has only been just over one month since I moved the family to Chicago from Madrid. It is always satisfying to have people (at least once a week) asking me directions and me actually being able to answer – but if you want to know how close I came to really experiencing what Chicago is about in the eyes of many, then the answer appears at the bottom of this piece.

Chicago has many good tourist attractions, and recently I read The Professor over the the T2 Impact blog, reaching out looking for advice about what tool to use when he visits (if you overhear two guys talking travel tech at a downtown bar after work in the coming weeks, it may just be the two of us). The guys at Montreal based mTrip last week gave me access to their iPhone app to play with, but I had to give it to an intern in the office to test out for me as unfortunately they don’t have a version for my BlackBerry. It seems mTrip are going after the lucrative revenue stream Lonely Planet has carved out for themselves, but I’ve also mentioned in the past the idea of airlines trying to get a cut of this revenue. As I couldn’t test it myself, I’ve added a taped demo for the mTrip product. The demo does make it look pretty useful for a certain class of traveler – ie. the guy who loves to plan each day of his vacation much more than I do.

Whilst that is really focussed on inspiration post booking, I was directed to something from a reader last week that I found interesting in the pre-booking inspiration space. In the Wotflight interview (that I referred to recently on Tnooz when discussing Hipmunk), Scott Moorhead referred to the natural search capabilities of Adioso. I’ve never been a huge believer in the hype around semantic search, but I notice Google search queries are continually becoming more intuitive, so maybe Adioso are going down the right path by pushing their natural language search story. The founders are from my home town of Melbourne, so another plus for them. In all seriousness, the search interface and subsequent results are quite nice, but I’m still not convinced that natural language search is something that managers of airline direct websites need to be losing sleep over.

The piece that the reader pointed me to which got me thinking of Adioso was a story in TechCrunch, but as can sometimes happen, the real gem was in the comments below the story. One reader added a link to a feature I had not seen before, but it is a really low tech answer to the new travel search that is a kind of shopping by affinity meets mystery flights. Much better to do something low tech and well, than over complicate things and fail dismally. To take a look at the German Wings idea, click here – but be warned, it is basic. For some reason I can’t fully explain, I do like it, at least for the time being.

So, what was the quintessential Chicago experience I passed on – if I was only referring to airlines, then maybe The Beat Live might qualify. Although I’m still considering maybe going to this conference in Chicago later this month, I just haven’t registered yet. Hopefully I do make it along to the W Hotel in a few weeks, but it all depends what else comes up.

No, I actually spent part of this weekend on the phone and email with producers from the Oprah Winfrey show about a segment they want to tape later this week – I don’t want to steal their thunder so I won’t spill the beans on the story angle, but for various reasons the segment unfortunately didn’t work for me in the end and I had to say no (I was only a bit player in a larger piece). Maybe if they had been interested in travel technology it would have been a different outcome! I’m sure what they had in mind would have been an interesting experience,  but this is definitely one case where an automated inspiration assisting travel search tool or mobile app pushing interesting activities to do in Chicago would have come up with a big blank. Sometimes you just have to be in the right place at the right time.