I flew my dog three times post 9/11 from Denver to Chicago by myself.
You need to prepare, and probably need help getting the kennel to the gate and checking in.
The airlines require a health certificate from a vet $25, it's only good for 7-14days.(One trip went longer and I needed a check-up on both ends.)
The airlines have rules: used to be no dogs if the temperature was expected to exceede 80F or go below 40F. (I got denied once on Christmas) So fly at the appropriate time of day to minimize the chances.
Each airport is different on how they handle the dogs, none are very good. They made no accomodation, and I had to stand in line with everyone at check in. From the check in line they will call a porter to cart your kennel to TSA screening, dog on leash still. TSA inspects the kennel, dog goes inside, and the porter takes the dog to the plane.
Cost: I paid as little as $200 at one time, now it is much higher $200-300 each way last time I checked. Each airline charges different.
At the other end: No matter how soon they bring the dog to you, it takes 5 minutes too long and you'll start to get nervous. I was 3 for 3 it worked out in the end, no meds for the dog.
If you are doing it SOLO, PM me and I can give you some more travel tips.