Disability Travel - crutches & carry-on coordination for connecting flights

I had the joy of acquiring a stress fracture in my foot while on vacation in CA. I'll be flying home in a few days and am trying to figure out the logistics of traveling alone on crutches with both a backpack and rolling carry-on bag--no checked luggage.

I've never been on crutches before and I can't imagine how I would be able to maneuver a rolling carry-on in them, not to mention through airports/onto and off of planes (and I'll have on a larger backpack as well).

I'll be flying from Portland to O'Hare to Dulles and then to a small airport in weyer's cave, VA. Obviously, when I purchased my tickets I didn't anticipate needing any special assistance from the airline (UA), so how/who should I contact and what should I request?

Any tips/advice would be very much appreciated. I'm a rather anxious person by nature so the more information I have and the more prepared I can feel, the better. I leave July 12.

Thanks in advance for any help!

Call and have them note your reservation. You'll be taken to the gate in a wheelchair and boarded first. You should be able to hold your bags on your lap and/or prop them on the foot rest. I always tip the person who helps me as they are usually not airline employees.

From United's web Site:

Home > Services & information > Children, pets & assistance > Travelers with special needs > Mobility assistance

Mobility assistance
Airport and flight connections assistance
United will provide in-airport wheelchair service at no charge to passengers with mobility impairments or other disabilities. This service is intended to assist passengers in moving through the airport to reach a gate area. Wheelchair attendants are able to assist semi-ambulatory customers in getting to and from the aircraft seat during boarding and disembarkation. They may also provide assistance in getting passengers to an airport lavatory, but they cannot provide any assistance within the lavatory.
In-flight assistance
Every United aircraft and gate area has available a specially designed wheelchair for mobility-impaired customers to use. These wheelchairs are referred to as "aisle chairs" because they fit in the aisles of our aircraft and may be used to move about the cabin.

Agreed. But you can also request wheelchair service at the airport (and you may have to re-request it at that point, even if you've called in advance).

Are you driving yourself to the airport? If someone is driving you and/or you're taking a bus or shuttle, you should be able to get wheelchair assistance from curbside check in on.

Allow extra time - since you're new to this, an extra hour is not unreasonable. If you're not in a big rush, you won't be as anxious.

Minimize your luggage as much as possible, remembering that the crutches are an extra thing to carry when you're being pushed in a wheelchair. Consider checking your roller bag. And at the risk of re-igniting the wheelchair pusher tipping wars (http://www.flyertalk.com/forum/disability-travel/886349-wheelchair-assistance-tipping.html), I'd advise you to take a bunch of small bills and plan to tip the wheelchair pushers.