Upgrading a flight to Italy - probability?

We got 2 coach tickets to Italy round trip with our miles. We have the miles to upgrade to first class, but we'd have to pay the reticketing fee of $100 for each ticket. We are willing to do this if we can get both tickets upgraded. The question is, should we upgrade just one if it becomes available, knowing that we may not get the upgrade for the other?

I plan on calling the airline daily to check for available seats. One rule: We will not upgrade if only one leg of the flight becomes available per ticket, because we'd be paying the upgrade miles for all legs even if we don't get it. We are flying Lufthansa thru Frankfurt to Rome.

If anyone has any inside airline knowledge or any personal experience with this, please let me know.

Thank you so much, this is the trip of a lifetime - going to see family there and travel Italy for 2 weeks, last big trip before we try to start a family.

Christine

We normally do the tickets/upgrade in one step, and only book when we can both get a guaranteed upgrade. This usually means being flexible iwth dates. Also, try for business class, it may be an easier upgrade. Business class on European carriers is very nice. I am not sure how much nicer First class is, but we find Business class very nice. Also, Frankfurt to Rome is a short flight. Try to get the upgrade on the Chicago->Frankfurt legs and don't worry about the Frankfurt->Rome legs. That will be very hard to find an upgrade, and may prevent you from getting any upgrade at all.

It may be worth it to go to the Luftansa ticketing office (you might have to go to O'Hare) and work in person with one of their agents.

If you do get the upgrades, make sure to take advantage of the ability to sit in the Airport Red Carpet lounge or the Luftansa lounge - quite nice and relaxing before your flight.

I would go for the upgrade even if you can only upgrade the Chicago-Frankfurt leg. Getting a halfway decent night's sleep is much more likely in business or first versus coach. The upgrade will also get you access to United and Lufthansa's clubs in Frankfurt, which have shower facilities. You can also get in if you have membership in the United club or if you're a United Premier Exec member. Also, business/first class flights within Europe are not that much better than coach. You get somewhat better food and a free paper, but the seats are sometimes the same seats as coach. And Frankfurt-Rome is a short leg.

We just returned from Italy and flew your same intinerary on Lufthansa. There is plenty of room in business class, so I second the recommendation to consider that upgrade. I also agree that the flight from Frankfurt to Rome is so short that the longer leg should be your prime consideration. I don't remember seeing any first class seats on the flight to Rome from Frankfurt.