My hatred to Chicago airports began back in December 2005. I was leaving SES Chicago, a conference, in a major snow storm. I headed to Midway (MDW) airport to catch my flight back to New York. The airport was a zoo, we sat there for hours, hoping to board and leave Chicago. It never happened. Soon after we were told to prepare for boarding (after waiting several hours in the airport), a Southwest Airline flight ran off the runway, onto the street and killed a six year old boy.

I saw the plane run off the runway. I did not know at the time that it hit any cars or anything. I didn't find out until the next day. What I did find out that the plane didn't just look like it was on the street (it was far away), but it was indeed off the street. It basically could not stop after it landed and skidded off the runway. Soon after, they closed the airport - all flights were cancelled.

Here is a picture:

Chicago Southwest Airlines December 2005

I had two options:

(1) Stay for the weekend

(2) Try my luck by going to O'Hare (ORD) to see if I can get on a completely booked flight and the only flight going back to New York via that airline that night (Friday morning).

I decided to take my chances, go on standby and take a shuttle from Midway to O'Hare. The shuttle ride took hours. The streets were a mess, it felt like an eternity.

When I got to the airport at about 2am, there was only one security gate opened. It was at the furthest terminal from the gate I had to go to. I went through security, which was meant for maintenance folks and then used the back walkways to go to the terminal I had to go to. I started walking through the empty airport to find a ton of people sitting and sleeping outside of a gate, the gate of the flight I was on standby for. I came up to the person behind the counter and she asked, "Are you Barry Schwartz." I said "yes." She said, you made it - you are booked on this flight.

So a few hours after that, we boarded the packed flight and made our way to New York. When we arrived in New York, the snow caught up with us. I remember driving home in the snow, this was after being awake for 30 hours or so. Wasn't fun.

That is why Chicago scares me.

Last night, the first snow storm hit Chicago. Flights north were being cancelled or delayed. I was with my wife and kid. We decided to go to the airport and see what was available. Luckily, they booked us on an earlier, but delayed flight. That flight actually ended up taking off earlier than our booked flight. It worked out. We got home, on time and safely.

Unfortunately, two of the three Continental reps were really not nice. The ticketing one asked if we want to be booked on the earlier flight, I said - sure. But I asked if we can be seated together and she said sure. When I went through security, I noticed she put my wife (with baby on her lap) in the back of the plane and me in the front. I walked to a Continental desk and the woman told me she couldn't do anything. She said there were only middle seats. I said, well - that is fine, is there a middle seat by my seat or her seat? She gave me a nasty look and said - um... I said, please just see what you can do. I then tried the elite access hint and she looked. She told us there was nothing in the front, only in the back. I said, that is fine. I got the tickets and I looked and she ended up putting my wife near me, in the seat she said was not available.

I am sorry, but that makes me mad.

Anyway, flying to/from Chicago is not fun. Chicago itself is a really nice and charming place.