5 Things You Should Ask Every Time You Check Into a Hotel

You don’t get what you don’t ask for. Elite status is only a start. Plenty of people have hotel elite status. It isn’t always properly recognized, and it isn’t always enough.

At a minimum you may want to avoid connecting rooms, rooms by the elevator, or over the HVAC system. On some stays you care more about the view, or size of the room, than on other stays. When it matters you need to learn how to ask for what you want. You won’t always get it, but it’s worth choosing from among 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 stick you in an odd shaped room without any natural light (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 job (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.

    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.

    Grand Hyatt Kuala Lumpur View of the Petronas Towers

  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 toiletries/free 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 hotel has 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. 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. Marriott and Hyatt guarantee late checkout for their elite members. Hilton and IHS Rewards 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.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. I can’t stand when a hotel is less than half occupied, and yet puts me in a connecting room next to another guest.

    Additionally, I always ask to be far from elevator, and yet, many times I wind up next to the elevator lol

  2. @ Gary — IHG guarantees 4 pm late checkout for Royal Ambassadors. Sometimes they will even allow as late as 5 pm-10 pm if you is important.

  3. Sorry this is almost all bad advice.

    1. How is your day. It’s disingenuous to ask when your motive is to ingratiate yourself to score freebies. Either way, what if the front desk replies that they have been super busy due to short staff, or some killjoy answer. Are you going to follow up with, “Man sorry to hear that, but you know what, how ’bout giving me a free breakfast?”

    Not all cultures welcome small talk between strangers. In many big western cities, the culture is one of anonymity. Many people are drawn to cities for precisely this reason, they want to mind their own business. So to them, hearing “how is your day” is a burden. They just want to give you your room keys and move on to the next guest.

    2. It does hurt to ask. It hurts your reputation because it makes you a cheapskate. If you wanted a nice room, why didn’t you book it. What kind of room do you have for me? Well, sir or ma’am, I have just the room type you booked. It’s on the 8th floor and elevators are behind you to the left, have a good day.

    3. Toiletries are free at all but the lowest end hotels, so an ask for things like toothpaste is completely appropriate (understanding that, if it’s brought to your room, you have to tip). Could you help make it special with a free breakfast? You know, I think you’ll find our breakfasts are very special and they are well worth the price.

    4. This one’s fine, but frankly, why take one person’s opinion when there’s Google. You can also ask in a travel forum, or the local area Reddit, with some context about your particular preferences.

    5. Sure I can give you a late checkout, it’s 50% of the room rate and you can stay until 4 p.m.

    Bottom line is don’t be a cheapskate.

  4. @ Yin Jing I’ve often thought the same thing about people asking for upgrades. If getting a better room or suite is important, than that person should book it.

    I also don’t understand people that try to give $20 tips to the front desk for something that’s hundreds of dollars in value. They seem like cheapskates as they’re offering $20 instead of paying hundreds more.

  5. I agree. These all make you sound smarmy and cheap. I almost can’t believe I’m reading this from a thought leader in travel. It’s positively debasing.

  6. I usually like you blog but this post is just too much for me. This is basically
    about asking for freebies. This posts contradicts the one you wrote not too long ago
    about Gregg and his free IHG status. There, you claimed you don’t accept any freebies
    and are always willing to pay for everything…

    Hopefully you don’t write any more posts on how to make people degrade themselves.

  7. I agree with “Yin Jing” and “credit”.
    Disingenuous, phony.
    How was your day today Gary? You had a brain cramp?
    I’m so sorry to read this.

  8. Anybody remember the hotel recommending a wonderful Italian restaurant nearby and the guests going there and realizing it was Olive Garden?

  9. I’ve heard if you dress nice and act like you belong in first class they will give you a room upgrade 🙂 Also in vegas try slipping them a $100.

    Seriously Gary I agree in principle that if you treat the front desk staff nicely they might return the favor however I don’t think you need to be fake about it. Just try to be nice to everyone and see how life treats you. Even if you don’t get an upgrade you might just brighten someone’s life for a moment.

  10. A rather rubbish post in my opinion (sorry). All the different proposal/suggestions here sounds so cheesy.


  11. Sorry mates, I agree with Gary 100%. Exercising courtesy and smiling while speaking with the hotel attendant is not “fake”, as some of the posters have suggested. It is only “fake” if you are a Mr./Mrs. Cabby Patty. Same principle applies when dealing with customer service over the telephone. A pleasant attitude is infectious. People in general like being around happy people. Most people working in a customer service role prefer dealing with happy people.

    As for asking for a better room, the category of room you purchased has many locations in the hotel. Some of those rooms do have better views or provide locations away from elevators and ice machines. Better room does not always mean an “upgrade”.

    Most hotels have a listed check-in time of 3-4pm. Rarely have I waited until then. Why? Because I call the morning of my check-in and “ask” if it is possible to arrive early. On a couple of occasions, I have checked in before 11am and on one occasion I checked in before 10am. Most of the time, I check-in between noon and 1pm.

    Asking for what you want is way better than hoping someone can “guess” what you want. Its interesting to hear some commenters disagreeing with asking for things. I wonder if they just waited for their company to provide an increase in salary or promotion. Maybe they paid the sticker price on a new/used cars. Heavens, I hope they didn’t pay the contractors first quote! Asking for what you want is the equivalent of negotiating.

  12. I LOVE this post…I’m all about getting free things that others pay for!

  13. Another garbage @Gary post. Trying to convince you, the reader, that just being a decent human being somehow deserves free shit?

    You want the presidential suite- PAY FOR IT
    You want the perks- EARN IT
    You want a good time- MAKE IT HAPPEN

    I think you need to re-evaluate your qualifications on this post, Gary. But it’s another one-sided post from a person who doesn’t even work in the industry.

    Prior to Gary blocking me on his twitter because I would call him out for click bait, he has yet to learn that facts matter.

    Start posting good info, not this click bait garbage @gary

  14. I’m not sure if I understand the logic behind why being at a hotel for a short time would warrant the hotel giving you a free breakfast?

    And then taking the front desk person’s local activity recommendation and using it as a justification for needing a late checkout seems kind of strange.

    I feel like some of these suggestions are a bit much. Although, it’s fine to ask how someone’s day is going but as long as you don’t have a specific motive connected to it.

  15. How to sound like a used car salesman and pull out every tired line that the desk agent has heard a thousand times before…

  16. The things I want to know:
    Has Hunter Biden stayed in this room? (hidden drugs/paraphernalia)
    Has Creepy Joe showered with his daughter in this room? (ewwww)

  17. Gary – Reading the posts looks like you & me are in the minority. I appreciate your insight and travel experience in this area. Amazing the personal spitefulness generated from a simple (often forgotten) comment “be nice maybe be rewarded” It takes a twisted mind to read into your comments the intent of duplicity or expectations. Checking into a hotel with a Standard King reservation who doesn’t believe the front-desk clerk has significant authority to offer a good room or a bad room even within a given category is being naïve and in my opinion foolish. Good news is the people who chose to attack you over a nothing-burger are the same ones getting all those bad rooms. Try smiling and having a drink to kill that bug up your ass.

  18. Disagree with Yin Jing.

    You have to be sincere and empathetic.

    If you are not normally sincere and empathetic then this strategy does not work because the check-in person will see right through you. You are trying here to make a rapport with another human being and also trying to follow the golden rule of not being an abusive jerk in a hurry.

    But having traveled in dozens of countries and met hundreds of people from every possible nationality working this job, I can confidently say that asking in a sincere and empathetic voice has worked well when I have asked for things. It also helps in the United States if the check-in person happens to be a J-1 visa holder doing this job as practical training to praise them and to ask them where they might choose to travel at the end of their training period.

  19. Ugh I would feel sketchy and like a cheapskate asking for things that way. Do people really think so little of hotel staff that they actually believe the staff doesn’t see through these false pleasantries and fake praises? If I don’t get upgraded I will politely ask if there are any upgrades available. They check the system and if there I get them. I don’t do a whole dog and pony show. I’m not there to frickin grovel and put on a false sense of excitement. If you want the breakfast then pay for it. Seriously I could see someone standing in line behind growing inpatient with some idiot trying to weasel a free breakfast that they are not entitled to out of a hotel clerk. Had something similar happen recently while picking up a rental car. Guy ahead of me wasted soo much time trying to get an upgrade that he was NOT entitled to and delayed me. He didn’t get an upgrade with all his antics. I got upgraded though right after him.

    About the only thing on this list that I will ask is for recommendations of places to go, but even that I am not bothering the checkin staff with questions like this. I’ll go to the concierge or if there isn’t one I will come back at a less busy time that is not checkin time. Of course, I am actually asking because I want recommendations not because I want to try to use it as a talking point to get some kinda benefit I am not entitled to.

  20. “I can’t stand when a hotel is less than half occupied, and yet puts me in a connecting room next to another guest.” – Yea this is a valid point. I usually forget to ask about this, but this is one of those things that if people are sensitive to noise they certainly can ask for it to be a non-connecting room. Asking to be further away from the elevator is also a reasonable request, although I never really had an issue being close to an elevator. Guess it depends on how much foot traffic there is on the floor, how loud the elevators are and whether hallway sound carries easily into the room. Both of these are perfectly reasonable requests on checkin.

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