Road testing the Cranky Concierge

I’ve known Brett Snyder aka The Cranky Flier for a few years now, so when he started up The Cranky Concierge, an itinerary management service this past month, I was naturally intrigued.

The concept goes sort of like this: most people hate booking and micromanaging their itineraries, figuring out where and how to catch and connect to their flights and lacing their travel together. As a self-professed airline nerd, The Cranky kind of digs it, and for a small fee, he’ll do it for you and help you along your way.

So on the way to Portland last weekend for a (lovely) drive through Oregon, I agreed to take it for a test run.

Below I’ve detailed how it went. Note that despite getting the service for free, I reserve no judgment.

Original flight: Chicago O’hare – Salt Lake City – Portland – Seattle – Minneapolis – Chicago O’hare.

Day of departure, Friday, October 16th.
Cranky sent me an email yesterday asking whether or not I wanted my updates via SMS or email. Even though I have a web-enabled iPhone I chose SMS, as I don’t have Gmail pushing email to my phone.This morning’s communication started off with a welcome e-mail, basically reminding me of my flight that day then giving me specific itinerary information including flights, flight numbers and weather along the route. The message even gets into the minute details naming arrival and departure gates, in my case telling me that when I landed in Salt Lake City that I needed to turn right out of the gate to get to my next flight.

At 3:30PM on my way to the bus, I received my first text message:

“Your plane will be arriving to Chicago at 5:49PM, so I would expect to be about 10 to 15 minutes late. Your gate is staying the same in Salt Lake (C3) – the plane is now in the air from Newark and will be gasp 20 minutes early – you should be on time.”

As predicted, my flight from O’hare left a few minutes late, though we arrived a little bit early due to some crafty routing by the pilots.

In Salt Lake City I was actually meeting up with my friend Al, who was starting in Santa Fe and who would be visiting Oregon with me. Pulling into the gate, I thought that I might surprise my friend getting off of the plane, so I sent an SMS to The Cranky asking where I could find his gate, including his rough flight plan and airline. Almost immediately I received a reply:

“Welcome to Salt Lake – Your friend landed at 822p WAY on the other side of the airport – gate E66 – flight 4696. BTW, your airplane [to Portland] has arrived, still at C3 departing on time”

By this time I was already on the move in the terminal headed for the Delta Skyclub, which when queried earlier, my concierge told me was just adjacent to terminal C. Locating Allan just short of the lounge, we pulled in for a few brief White Russians before heading down to C3 for our quick flight.


Two evenings later the cycle started again, with The Cranky sending me an SMS several hours before flight speaking on the weather, inbound flights and the general state of my upcoming journey. My unfortunate connections through Seattle and Minneapolis meant that I would be traveling through the night, but The Cranky stayed through Seattle, where he expertly guided me out of my gate, towards the S terminal and through the Skyclub. Before long, I was at work in Chicago with a massive headache, two hours of sleep and an internal promise to never fly a redeye from the west coast again.


Onto the real question though: was it worth it? I see the big advantage of the Cranky Concierge in the management of complex or multiple itineraries. Whenever problems arise at the airport, its always nice having someone behind a computer who knows the right numbers to call, where the closest Subway is and how to get you home fastest.

The term “complex” also depends on the traveler. One can image a first time passenger, lost at an airport who needs to know what gate to head to. On the other side of the coin, a million mile businesswoman could not have enough time to manage her itinerary and may only want to follow directions from her dedicated concierge. Both could easily find value in this service.

For a person like me who knows how to work the system and is used to micromanaging itineraries, it’s not as useful. At least not on this trip. I’ll admit that I’ve been in the situation once or twice where I’ve been stone cold lost and hungry at a strange airport in a strange part of the world and have needed help, but this weekend was not that time. Perhaps some day I’ll need that safety blanket.


Brett Snyder, aka The Cranky Flyer offers per trip itinerary management from The Cranky Concierge. Services include flight planning, flight monitoring, delay and cancellation assistance and post-trip dispute assistance. Prices range from $30 to $80 per trip, while a subscription-based service is in the works.