Luggage Logistics - Weird Flight Routing
 

Why do I do these things to myself?

I wanted to be on the first AA flight from PHL to ORH and back, so I bough those tickets a few months ago. Since I live in Worcester, that also means I need to get myself down to PHL first. I now found out I will need to fly to DEN that weekend, ideally that evening but possibly early morning the following day if I need to.

Ideally, I would fly down to PHL with luggage, have some place to leave it there while I fly to ORH and back, and then take it with me to DEN. But how can I manage that? I could check the luggage this time, but I may be flying UA and I don't know if I can check it inside security that far ahead of time. I could always get a hotel room for the day, but that is awfully expensive to hold luggage.

I'm a little confused. How long do you need to store it for?

I have had luck at some hotels, but not others, to store luggage at the bellhop without actually staying there (convention centric hotels almost never seem to be a problem). I always tip pretty well upfront for that. As another thought, I've never done it before, but would it be cheaper to rent a car and put the bags in the trunk and then drive it to an airport parking lot? Probably get a free shuttle from the lot back to the airport, and even with airport parking fees, it is probably cheaper than a hotel room and just as secure.

is the turnaround time in ORH long enough to where you could run back to your car (presuming you could park near the terminal) for the bag after arriving from PHL?

about 12 years ago I was flying back-to-back trips on UA to ATL and BOS in Feb; ATL was in the 70s and BOS was getting freezing rain and snow ... I packed a separate garment bag for each trip, left the one with my overcoat and a couple sweaters in the car in the terminal garage at IAD, and swapped bags during the 1+15 connection

It would be close, as security in ORH is a pain. But, my car will be at BOS since I can't get down to PHL before the first flight. I like the car rental idea, but I don't think I will have enough time between flight sin PHL, as the flight to DEN leaves 1:30 after I arrive, and I expect the ORH flight to be a little late due to festivities.

I could try that.

So just to confirm - you're doing
Ticket 1: BOS-PHL
Ticket 2: PHL-ORH-PHL
Ticket 3: PHL-DEN//DEN-BOS

Correct?

If so you have a few options:
1. Don't pick up your bags from BOS-PHL, then pick them up when you come back from PHL and check them with UA. The cut-off is T-45 mins.
2. Check bags with UA early - they should let you do that as they have numerous flights ex-PHL. You may want to make sure you can do that before picking up your luggage in PHL.
3. Don't check lugagge :P

Option 3 is the preferred. Problem is PHL to ORH and back is an E145. So that means gate check - yuck. But I suppose that is going to be my burden - I don't want to risk loosing it along the way. I've seriously considered picking it up while I am in ORH, but I don't think there will be enough time.

Ship the bag (i.e. UPS Ground) to the hotel in Denver earlier in the week.