The 5 Things You Must Ask Every Time You Check Into a Hotel

Back in June, Chris McGinnis offered 5 smart questions to ask at check-in. These were mostly questions about your room.

It was advice to avoid connecting rooms (noise) and ADA rooms (messy showers), and also to make sure your frequent guest number is on file.

All good, basic stuff, but you can do better. You can learn to ask for what you want. You won’t always get it, but it’s worth asking these five questions if you want to improve your stay.

1. “How is your day?” You’re checking into a hotel with a person most of the time. That person has good days and bad days, they can help you if they want or give you the room over the HVAC system (even if you were pre-blocked into a nice room, you can be moved!).

   You want to develop a rapport with the agent. Theirs is a generally-thankless thank (except where tipping is involved). They deal with everyone else’s problems. Be nice.

2. “I’ve really been looking forward to this hotel for its..” and finish the sentence as appropriate, views of the X, great big rooms, what have you. “I’ve needed this trip for awhile. What kind of room do you have for me?”

   Now, you’ll find the most extensive advice on how to ask for and get an upgrade for free in this post, complete with video.

   And just asking doesn’t mean you’ll get the Presidential Suite. But it doesn’t hurt to ask. If you’re nice, and get the check-in agent on your side, they might at least help you out with that better view.

3. “I won’t have nearly enough time to enjoy the hotel as I had hoped and wonder if you could help make it special. Would you be able to give me complimentary…” and finish the sentence, breakfast/extra toileteries/Internet.

   Again, know what you want and ask for it, small items can be granted, different agents have different levels of discretion and it varies by hotel. They get asked for things all the time, and the answer is most often no, but it could also be yes.

4. “This is such a great location and I don’t have a lot of time here, what is your one favorite place to..” and ask what you’re most interested in, eat/drink/relax/etc.

   Take advantage of local knowledge. It’s like asking a cab driver for the best food, you may discover some place new. Do not ever ask because the front desk agent doesn’t know you and will probably assume you’re the same generic idiot tourist they deal with every day. And give you that same advice. What you want is their knowledge, so you’re asking where they would go, or where they would tell their best friend from out of town to go.

5. “What a great suggestion, I’m going to take you up on it. Could you give me a late check-out, in case I wind up up/out late because of it?”

   If you’re reading this blog there’s a good chance you’ve got some kind of hotel elite status. Starwood and Hyatt guarantee late checkout for their elite members. Hilton, IHS Rewards, and Marriott do not. But even the guarantees have some limitations, and they’re always dependent on the willingness of the local property. So develop that rapport, ask the check-in agent’s advice, and then make a final ask that flows naturally from the conversation. It can be for late check-out, or something else that makes the say — in the context of what you’ve already been talking about — that much easier or special.

Some of these are long shots. But asking is cheap.

Sometimes — even if it is just 10% of the time — you get a yes. And that makes the strategy pay off, as long as you do not mind getting a no the other nine times That, incidentally, is also really good dating advice.

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