Benefit to checking in online a day before?
 

I'm traveling for work Monday and Hilton offered me to check-in online now, and to "just swing by for the key" when I arrive. I'm wondering if there's any benefit to it since I'll still need to go to the front desk - maybe by getting online earlier there's a chance at an upgrade as Gold? But on the flip side if there are travel disruptions (currently my flight is not affected by the southeast weather but things could change) will being checked in affect my company's ability to modify, etc.?

The advantage is you may be able to lock in a really good room, especially if they've pre-upgraded you to a higher room class. A related advantage is, if you're arriving late, you can prevent being assigned the dregs, which is particularly important at hotels which do not pre-block room assignments. There's a thread on this, and the general consensus is you need to make a judgment call whether you're likely to do better with the mobile room selection or at the front desk.

Hilton is IME the only chain where mobile check-in can in fact provide a meaningful benefit.

I agree with Kacee. I always try to do the online check-in. If I have been pre-upgraded and get to really choose my room, I complete the process. If I don't see the pre-upgrade and think that I might do better without completing the process, I just let it go. The message when you do the check-in is that they will still try to upgrade you when your arrive in the hotel but some hotels are really cheap (recently there was an example on the Hilton threads about one of those hotels in Boston) where they tell you: "Well you chose that room, so you stay in that room".

For the uncertainty about being able to get to the hotel if the weather is really bad, I consider that I already have a problem with that since all the hotels have a cancellation time. The Hilton I'm going today used to have a 48 hours cancellation, it just switched to a 72 hours. I think if the weather is really bad, the hotel can make a judgment about that and not penalize you for already checking-in. Not only that, but if you end up having to pay for the first night and you are traveling for work, work better pay for it. My employer does that. As it should.

Yes, this is key. You can bail on mobile check-in if you don't like the room choices. I do that about 50% of the time.

Haha yeah, coming from Hilton and now spending a lot of nights with Marriott, I always get a good chuckle when Marriott asks me to do OLCI - it consists of clicking a button and being told "Great, that's nice; we haven't upgraded you or assigned you a room, and you'll need to go to the desk when you arrive". What the purpose of their OLCI is, I have no idea.

Even better, on a Hyatt stay three nights ago (Bloomington, MN), the property claimed I was downgraded from my paid suite to a basic room because I had used mobile check-in (which had seemed to me like a good idea with a midnight property arrival). They were likely making stuff up, but still . . . .

You can still cancel as per room terms after you have checked in.

I rarely see a significant upgrade offered with OLCI, and I no longer accept the "best of the bunch" despite the "we'll do our best to upgrade you" statement. Once, I selected a room and, when I arrived at the front desk and asked about an upgrade, I was told that they would have already upgraded me (as a Diamond), but the front desk staff are not allowed to touch a reservation when the client has selected a specific room.

Pre-selecting, or even checking in on OLCI with the offered room, also carries another risk: The complimentary bottled waters and sometimes a welcome letter from the manager may already have been placed in that room, and the front desk staff may want to keep you there instead of making a change.

I had one instance where the hotel charged for the night because "I checked in online and there was nothing they could do". The good side is my reservation wasn't cancelled since I was checked in and my room was waiting when I arrived the next day.

Since it was business, I didn't argue but I think it was a BS answer.

Which is true to a degree, you've selected that room as far as they're concerned, however if you're stood at that desk then that's a different matter.

This is my main reason for online check in. If I am arriving late, I want to make sure I'm not stuck in a closet by the elevator.

^ same. Last time I didn't check in, arriving late, I ended up with the worst stay I've had in years. Wrong room type, right across from the elevator, and on a low floor under some of the noisiest people I've ever encountered in a hotel.

That's why I said that I only complete the OLCI if I have been upgraded to the Executive Floor and, even more, if I have a choice of many rooms in my upgraded floor.

I only care about a letter from the manager if it comes with chocolates and wine. In the US, it never comes with anything for me as a Gold. In Europe and Asia, most times the letter comes with something really nice but then in Europe and Asia I'm upgraded to the Executive Floor 98% of the time and the Executive Floor has wine and pastries. If the letter from the manager comes with fruits, I'd rather not get the letter and the fruits as they end up rotting in the room.

In the US, I end up being upgraded to the Executive Floor about 75% of the time.

If I don't have water in my room I ask for it when I go to dinner. It's usually in the room by the time I come back from dinner.

Online check-in the day before is for me has mixed results. Some hotels either pre-upgrade you or open OLCI with upgraded rooms available to you. If you see a room you like, particularly if you know the hotel well, then it's one thing less to sort out on the day, particular if you can get the Digital Key to work. And that feature is generally getting better in my experience. When I find myself at a Marriott in particular waiting to check-in I am reminded why I prefer the Hilton family.

The caveat is that in some locations, perhaps a majority, you may get an upgraded room if you check in at about 7 or 8 am on the day of arrival, local time. I haven't totally understood the process, but some local practices seem to keep the better rooms back, and if the hotel is going to be relatively busy they won't necessarily give out an upgraded room the day before. If you know the hotel is going to be full, and the better rooms aren't that special, then you may still want to check-in the day before to at least get something acceptable.

If you don't know the hotel well and if you have particular factors that are relevant in room choice then you best check in on the day, particularly if you aren't arriving late. In that respect it's unfortunate that the App / web check-in does not disclose all room features (e.g. shower versus bath tub, refitted room).

Clearly at Hamptons, Tru, HGI (etc) then typically all rooms are the same anyway so there isn't much reason to wait, other than if (e.g.) you booked a twin room but you'd rather have a king or queen bed.

Mostly I do check-in online, and use the Digital Key, but it may well be on the day of arrival. I almost never change room after that but I know I have that option if necessary.