Pros
If you are going to work in Chicago in technology, you have several options. You can go work for a bank or one of the financial variants - if you like working on old tech. You can go work for a startup which will be cool and interesting, but you gotta be willing to take the risk of looking for a job in 6 months when pimentoloaf.com runs out of funding and closes its doors. Orbitz stands as a unique option in the Chicago job market. Plenty of new tech pushing out of the old. Lots of opportunities to take part in communities outside of work (look for yourself: erlang, hadoop, etc). Got an emergency and need to bolt? Go! Great work/life balance. The company is open about whats going on -- the good stuff and where we need to improve. Good luck getting that kind of openness at another company this big. Most importantly, the chance to work with people smarter than you to keep pushing you to bigger and better. Want a place to just hide and collect a paycheck? This isn't the place. We work hard and we love it! You got the chops? Join us!
Cons
It is a big company and like any big company there are certain necessary evils. These usually fall onto groups that have hundreds of people to serve but only a few to do the work. HR, IT, etc. There is usually some process involved. Computer's crashed? You may get stuck in line behind the network outage -- sorry. Not the kind of response you'd get at a startup ('cause there are less than a dozen of you). Realities of large companies... HR forms (granted most are electronic), expense reports, etc. Deal with it and get back to your cool job. These should be the worst thing you have in your life!