Award travel

Separate tickets, so you move the luggage.

You might want to travel with carry-ons only.

Agree you should do carry on only. If you check a bag in Milan, you will need to get the bag at IAD and then re-check it. I'm not familiar with IAD, but my guess is that you would need to exit through international security and then re-check your bag, basically like starting over with new flight. Because from the airline point of view that is what you have, a new flight, not a continuation of travel. Two hours is not enough time to do all that. If you have a carry on, you should be able to navigate security, customs, etc, in under two hours. But you probably should do on-line check in for your final leg back to IND, so that you have a boarding pass in hand. That way you can just make your way to your domestic gate for the final leg, hopefully avoiding some security lines and headaches within IAD. For more specific info on navigating IAD, I suggest studying their website and also look at flyertalk.com, that forum has a lot of expert advice.

Two hours is plenty to do all you have to do at Dulles, luggage and everything.

Grier, I'm very familiar with Dulles. What airlines are both legs on? There are two immigration areas in Dulles. What happens depends on which airline your international leg is on.

Laura - All flights are on United.

Grier, First make sure it is a non-stop flight from Milan (MXP?) to IAD. Currently, United does not have a flight out of Dulles to Milan (they route you via Newark) but perhaps they are adding a new route and haven't announced it. If both flights are on planes operated by United, they should be able to check your bag through to IND. You will need to show them both of your tickets in Milan and ask them to do this. Some airlines are no longer willing to interline bags on separate tickets, but I haven't heard anything when both flights are operated by the same carrier. Your bag's destination is important when on an international United flight to Dulles. Dulles has two different immigration areas. United international flights generally arrive in the C terminal. Connecting passengers go through immigration in the C terminal which is the terminal where most United flights operate out of. Passengers terminating in Washington get on a mobile lounge which takes them to the International Arrivals area in the main building. The luggage is directed accordingly. While I think it is possible to do this, I would probably try to get a longer layover on two separate tickets. Usually, I've zipped through immigration and customs, but I had one flight where it took me 30+ minutes to get through immigration and another flight where a container got stuck in the luggage hold and it took the airline over an hour to get the bags to customs. Here is the detail for international arrivals at Dulles: http://www.metwashairports.com/dulles/884.htm

Are you sure you have to pay for the leg from IAD -> IND? Are you sure you really need (or want) to go via IAD at all? A quick look at United's award calendar next fall shows seats available all the way from MXP to IND virtually every day. None of the United flights go via IAD (they all go through EWR), but there are other routings on other airlines, including a couple that do go through IAD or DCA. If it were me, I'd just get the award ticket MXP > EWR > IND and not worry about it - you're on one ticket, so you (or your bag) would be accommodated in case you misconnect. If you're on two separate tickets, you could be stuck. If you do it all as an award ticket, it costs you no more miles. Unless you have some reason to want to pay for the extra leg...

Do you really need to fly out of MXP? Which segment is actually holding you up? Are you sure that they are looking for star alliance availability, or just United seats?

Is it no longer possible to buy one entire ticket and pay part of it with award miles and the balance with actual money? Did you buy a one-way ticket to Milan, or am I not understanding the post? Do I need coffee or what?

Thanks for your responses. I'm planning a trip to Italy next fall. I don't usually plan this far in advance but thought it would be easy to use miles for the flights. I got the outbound flight the first day it was available. For the return, there have been no Saver award seats available for my date. Reviewing my options: 1. Keep trying and hoping that a Saver award comes available. If it doesn't, will have to buy a one way ticket at some point. 2. Use miles for the Milan to IAD or other intermediate point, and buy a ticket for the IAD to IND part. Zoe, I called yesterday and was told I couldn't combine two payment methods (award and money) for one ticket. I can fly carry-on for my outbound flight but will likely check a bag for the return flight so I was concerned about re-checking my bag at IAD in the two hour time frame. I should be able to check into all flights in Milan and I was hoping they would check the bag through to IND even though it would be two tickets but wasn't sure. The flight is Milan to ZUR on Swiss Air (partner of United) to IAD on United.
3. Buy additional miles to qualify for a Standard award ticket where there are several options available for my date for Milan to IND, including the one-stop Milan to EWR to IND option. United has a 25% off deal now on buying miles. Option 2 ($255) would be cheaper than Option 3 ($536) but would have some uncertainty with it. I have no flexibility in my date.

If your airline is in an alliance with other airlines, as United is, call their 800 number and talk to a real person. They may be able to work out flight arrangements for you that will get you around the way you want. I did notice that on United, it "costs" more miles to use their partners. That may be a deal breaker for you. I suggest you call that 800#, anyway. See if you can get some help there.

Even better than talking to an agent is to do your own search online - the new UA (old Continental) booking engine is awesome for award travel searches. Try breaking the search into distinct segments and then search individually. I have generally found that Air Canada has lots of availability - this may also be an option using a combo of AC, UA, etc. - may add an additional flight but will save you $s.

Grier, Be patient. Here is my story. I began looking for a 'saver' flight from Chicago (ORD) to London (LHR) for my wife on July 1 for a June 2013 flight. Unfortunately at the time, there were no direct 'saver' flights to LHR. I kept looking daily and on July 20th I decided to book a one stop 'saver' flight from ORD to LHR via Newark (with a 4 hour layover). Yuck. But I needed to get my wife to London by 7:30am on a specific date and I was afraid that I would lose my 'saver' ticket option. I kept looking EVERY day on United's website which, as mentioned earlier, is excellent. Finally, on November 21, BINGO. A direct 'saver' flight ORD to LHR showed up with a 5:55am arrival. Exactly what I needed. Since my origination and destination cities were the same I was able to change flights for no additional cost. I realize that your situation is slightly different in that you haven't been able to snag a 'saver' flight but my point is that you should keep looking. I know that multi stop 'saver' flights from MXP to IND exist from time to time as I picked a date (Sept 28) and there were two such flights. Hopefully, a 'saver' flight will surface for your date. An option to consider is to book the 'saver' flight MXP to IAD (don't buy IAD to IND) and KEEP looking for a 'saver' flight from MXP to IND. If you find it, return your miles to your account (cost is $150, I think) and immediately rebook from MXP to IND. If a 'saver' flight doesn't show up, buy the IAD to IND leg sometime next year.

Thanks, Tom. Yes, that's definitely an option. I have been checking several times a day and there haven't been any Saver flights for my date but there have been for other dates, even for other Sundays. Must be something going on in Indy that weekend. I will keep checking. Thanks, again.

Grier, why do you need to go to IAD? Why not MXP to EWR, or any of the other major hubs? Or why not ZRH to EWR to IND? My feeling is that you are focusing on IAD, but may be missing other options? For award seats, a little bit of flexibility is important (which often means longer times)

Nicholas - I don't need to go through IAD and have been checking other connections for several days. The flights through IAD had the best times and connections for me. Unfortunately I don't have much flexibility this trip. Thanks for responding.

Grier - Have you checked each leg of your entire return trip for saver award availability? A couple of years ago, I couldn't get a United saver award on the date I needed from AMS to SFO. But when I called, they were able to piece together an AMS to LHR flight and a LHR to SFO flight together as one saver award ticket flight. They searched the LHR to SFO flight first and then somehow added on the flight from AMS to LHR for no extra miles. I did have to call back a couple of times to get a knowledgeable agent who understood what I was asking...

Grier, Hopefully you will be able to work out a flight all the way home. However, if you do end up at IAD then: 1) If you are able to check your bag all the way to IND, 2 hours is plenty of time barring no delays. 2) If you are only able to check your bag to Dulles, you would need to go over to the main terminal baggage claim and then go back through security to your terminal. There are security checkpoints on the lower level by baggage claim and ones on the upper level by ticketing. Usually the lines at the security checkpoints on the lower level are much shorter.

United charges $25 a person to get help from a human, and for me last year it was well worth it. Got a good agent who used Swissair for the "missing link" part of an AUS-EWR-GVA-ATH/FCO-IAD-AUS itinerary. Note that they charge $25 per person whether or not you accept a suggested itinerary; I had status then so it might have been easier, but I had no luck clearing any seats at all in several weeks of obsessively checking for award seats.
Know which flights you want and have tabs open on your computer with the potential connections. Surely $25 is less than a one way ticket.

Thanks, everyone.