We always ask for upgrades, even when booking a room we're happy with.

But I can't shake the feeling that the check-in person is thinking, "cheapskate... another guy looking for a free hand out.... why didn't you just book this room.... if you can't afford it, why stay here.... blah, blah, blah."

Now, no one has ever been rude about saying yes or no, but I still am not quite comfortable when asking.

Thoughts?

I don't feel cheap. If they don't want to give you the upgrade they won't.

I have gotten free gps on cars and free rooms at hotels.

I look at it this way: the worst they can say is no, and the best they can say is yes. Chances are that the person behind the counter (if they are smart consumers)would do the same thing if they were traveling and trying to maximize their experience for their hard-earned money.
If you have guilt, you always have the option to pull out some tip money when you ask. Maybe that will help you not to feel cheap. It isn't always needed, but sometimes it helps, and maybe giving away some money for the upgrade would help w/whatever the cheap-guilt thing is.

It's odd, because it would never occur to me to ask for an upgrade unless I had a really compelling reason. If I want a "great" experience, then I should arrange for it. When I have gotten an upgrade, I always appreciate it, but I don't expect it nor do I ask very often. It seems a little "cheap" to me.

I'd feel even cheaper trying to slip an extra $5 to the clerk as I asked for it. It's one thing to ask if an upgrade is available. It's even cheaper in my book to try to cheaply "bribe" for one.

When I worked at the front desk in college, I would never give an upgrade to someone who asked for one. I would only do so for people who were kind and unassuming as a way to brighten their stay (not that people who ask for upgrades aren't kind but I just felt like it took the fun out of trying to make someone's stay extra special).

That's interesting KC.

So it was basically at your whim? No real rules about it?

Yeah, I guess you could say it was at my whim. The hotel never had any guidance on what rooms to place guests in unless they were paying for a certain type. I always tried to always place people in the best rooms available and felt embarassed to put someone in a room overlooking the roof or something like that if there were nicer rooms sitting empty. I guess you run the risk of guests always expecting to be upgraded but I never took it to the extreme - just a good view or a slightly bigger room. But, in all of my travels, I have never encountered a front desk rep with the same mentality as me. I never ask for upgrades and always end up with the run of the mill room.

the best way to get upgrades is to join the hotel's guest program. it is free and means if they have a better room they'll give it to you automatically.

The only times we ask for upgrades are when we are checking into hotels we go to frequently. My husband is liked at a couple of hotels in Las Vegas and we never even have to ask.
In Montreal, our hotel gives us a break on the cost of rooms, because we have been there so many times.
Even in Paris, our favorite hotel gives us a break..people appreciate repeat business and sometimes show their appreciation.
Airlines never charge the same amount for every seat anyway- we have paid for upgrades when flying so there is nothing too cheap about that.
In the long run, we pay, so we never feel cheap.
And I so agree with Patrick

I wouldn't say it is automatically "cheap." It all depends on your mindset and frequency you do it. Every once in a while just to see if it works, no problem. However, if you're doing it often enough you're starting to feel guilty and in such a manner you're getting vibes people think you just have your hand out, it might be time to cool it for a while.

We recently had the chance to spend a few nights in a
$283 hotel room for $75. We treated and were treated the same as the folks next
door. We didn't "invent" the policy, the corporation did. If I am in a position to inquire, I do so. I don't think any seasoned check-in person
is thinking "cheap", I think they are thinking "I've got 10 such availiable
rooms and I get a kudos for booking them." Kids, it's all about sales.
It's a business, with a bit of kindness
thrown in ('and please will these folks I've upgraded tell their friends and associates")
thriving on referrals and returns.
Politely requested with a nice smile
what is harmful about that?
R5

I reread you original post. I was not talking about asking every time for no good reason. The times I ask are when I go into the room assigned (or can tell from the clerks description at check-in) and don't like it- it is small, it is near the elevator and noisy, etc. Recently I stayed at a hotel in Houston and was put next to a noisy ice machine. I asked to be moved, and was told there were no non-smoking rooms. I was nice to the desk clerk but obviously bummed as I knew I wouldn't be sleeping well. Somehow, a few minutes later, she called me and said she had come up w/a room, and it turned out to be bigger and much quieter. I tipped her-I think she went out of her way to get me that room.

I agree with Mike and Patrick. But it sure is a thrill when it happens unsolicited!

I do think it's okay to ask for airline upgrades if you are a member of their "club" level, or a FF.

Yes, I have a hard time asking for upgrades. And I've never been given one spontaneously - even by joining the frequent guest program! Sometimes I feel lucky to even get the room I paid for (no smoking, two beds)!

The first and morst important tip Frommer's Lil Black Book of Travel (I think thats the name?) lists is to ALWAYS ask for an upgrade when checking in. Always. And of course, always ask very politely AFTER you've chatted a bit with the clerk. All they can say is NO and often they will say yes.

So yes, I ask every time on both business and leisure travel and while I've never kept track, I am upgraded the majority of the time.

This thread deoicts almost exactly what happened when we checked into the Aladdin last week. I had made reservations several months ago. We were having a triple celebration vacation: our 33rd anniversary, my birthday and celebrating my retirement from teaching after 34 yrs! Having read Fodors comments I decided to ask for a "nice" room from which we could see the Bellagio fountains knowing that was NOT what I had paid for. At first the clerk looked and told us "Yes. There is one available...it will cost you $30 more /nite." So I smiled and said "HMMMM, for $150 I'd rather see a show or gamble. Thank you." We continued our check-in process and then the clerk suddenly said "I'm going to give you a better room at no cost." I was flabbergasted and naturally thrilled.
When we arrived in the room (by the way they let us check in at noon - 3 hrs. early) we opened the curtains and had a great view of the fountains. My husband then returned to the desk and tipped the clerk $20.
So it doesn't hurt to ask nicely although it made me think how many people may say the same thing even if it isn't their birthday, anniversary etc.!!!

teacher- What was the reaction of the clerk to the $20?

My husband isn't right here with me but if I remember correctly when he came back to the room he said that the clerk thanked him. No big reaction so maybe we should have done that automatically at his offer???? (My husband later confided to me that he hadn't tipped him at first because my husband wondered whether the room was really going to have a nice view or were we going to have to lean over and see a corner of the fountains.) I had read about people giving the clerk money as they asked for an upgrade but that definitely was NOT something I felt comfortable doing.

I'm actually a little surprised that people tip at the front desk. It seems even more condescending then asking for an upgrade every time you go to a hotel or airport. Essentially, you are offering a bribe since the front desk person is not providing you a service but just plugging you into a room.