I'm a long time user of TripIt, but I've gotten to the point where several issues with it really bother me. They aren't fixed in TripIt Pro, so that's no help. I'm starting to migrate some trips over to Kayak's mytrips. I'm wondering if anyone here has gone from one to the other and could compare the two. Here's my initial overview. Speed - So far, what I dislike about TripIt is the speed, especially when launching the iPhone app (it always wants to update on launch, which is a real pain if you are trying to get a bit of info out of it in a hurry - and if you have data off or your wifi is spotty or whatever). Kayak definitely seems faster in this regard. On Kayak, updates are manual! Looks - TripIt wins hands-down. Info - Pretty similar. Kayak doesn't add driving directions, but I'm not sure I use those that much anyway. Flight Status - Free on Kayak; $49/year on TripIt Info Processing - Much faster on TripIt, but more flexible on Kayak. If TripIt can't handle an email, they dump it back to you. If Kayak can't, it seems like a person actually reads and parses the data and enters it in. It can take hours, but it's free, and, so far, accurate. Am I missing any other issues that are important to other users?