90% of the time, I'm buying my tickets at the counter. This is the case even with me having 20k status and Discount Den.
1. Buying at the airport is almost always cheaper than online even when you factor in the DD price. I always check the math. I do this by taking the non-DD price and subtracting the CIC charge from it and comparing it to the DD price. Usually, I save $46 total ($23 a segment) per itinerary. To some that may not be a lot. To me, that money I saved can buy me another RT ticket. For example, I was looking at a RT ticket for LAS-MDW. DD price was $70, non-DD price was $84. I booked it at the airport and it ended up being $38. That money I saved I actually used it to buy another cheap RT ticket. The only time I buy online is when the DD price is usually $30 or more dollards cheaper than non-DD price.
2. I take at minimum 1-2 RT flights a month. That gives me 4-8 minimum opportunities to buy a ticket at the counter while I'm there. This way I don't have to spend extra time going to the airport just to buy a ticket. I will already be there.
3. Even if there is a line, I don't mind waiting 9/10 times since I'm already waiting for either my flight to depart or waiting for someone to pick me up. If the line is too long and I can't/don't want to wait or there isn't an agent at the gate, I know I will have more chances later.
4. I have a pre-written out slip of all the info needed for booking for the agents to make it easier for me and for them. This reduces mistakes and lets them double-check any information they're inputting. The agents appreciate it and I do hardly any talking.
5. Sometimes my benefits are added at the counter and sometimes they aren't. It all depends on the experience of the agent assisting me. I have no problem spending 30-45 seconds adding my benefits to my booking if they are not able to. This is fine at the 20k and 50k status levels.
The only people I can say that would benefit the least from this are people with 100k status. Even then, it depends on what is most important when you're booking. If you need/like the flexibility to cancel and get a refund, need a checked bag, or are traveling with a group who needs luggage, then I wouldn't recommend this and you should book online. If price is key, then booking at the airport will still be a good bet for many. Yes, you don't get the WORKS bundle. However, you do still get a free carry-on bag, priority boarding, and stretch seating (group stretch seating if you need to as well) which may be all you need for certain bookings.
Just my two cents.
