I'm a 1K needing about 15 additional segments by the end of the year to requalify. Hopefully UA will do the Double EQS promo!

Can you recommend the cheapest possible Segment Run from ORD? I would be flying these end of November/early December time frame. I hear the ORD-IND route is a fairly inexpensive one that I could devote an entire day going back and forth on. But perhaps there are better ideas out there?

Thanks for your help!

I, too am based out of ORD. I think I'll be within striking distance of 1P with a segment run, so I was trying to figure this out myself.

It might not be comfortable but using ITA I found segment runs (unfortunately using a lot of US metal) from ORD to PIT. (There was a thread in the mileage run deals forum that mentioned this routing.) I'm probably not the best searcher on the ITA system, but I found runs of 6 segments in a day. I didn't find any other cities that looked more attractive / feasible. Still, I'm worried about hitting a day with bad weather.

ORD - MSP/IND/DTW/ all on mainline airplanes. I can get 5 segs in per day if the weather is good. IND is going to start getting a little harder as they pulled 500/985 out of the system. I guess UA finally caught on to what I was doing :)

Anyway, a bunch of one hour flights back and forth. If you aren't planning anything for a Saturday it will take up the whole day. I've been known to pull 10 segs in one weekend. $118 r/t ai for each of the above routes.

I've only been asked a couple times what I'm doing by the FA's since they were on my morning ORD - DTW r/t and then joined me on the ORD - IND r/t. They didn't seem to care though, just shrugged and said, "It's your money."

Depending on which part of the year you are looking at, UA has added one mainline trip back on the ORD-IND route, but the scheduling is not as convenient for MR's.
I have sometimes found IND-ORD-xxx-IAD-LGA RT for $139-169(all in)(usually for Saturday travel) so for somewhat less you can get 6 segments when starting at ORD. Yes, this routing is especially weather sensitive, but I've had surprisingly excellent help at the IAD RCC when things go bust.

Some four-segment itineraries available on 2 Dec:
ORD-BUF for $149, stops in IAD outbound and PHL inbound. 1/4 US.
ORD-PIT for $139, stops in IAD outbound and PHL inbound. 2/4 US.
ORD-SDF for $136, stops in PIT and CLT outbound. 2/4 US.

However, for truly high segment yield you'll need to do the grand US Airways tour. ORD-PHL-PIT-BDL-PHL-ORD on 10 Nov gives five segments for $157.

Too bad that UA's $98 BNA fare appears to only be for nonstops.

How do I book some of these multi-leg fares on .bomb?

Generally, I've found that you don't book these itineraries on .bomb. I have sometimes had luck figuring out the itinerary with ITA, and then setting up a multi-city itinerary specifying exactly where I want to go. I can sometimes get to confirmation screen (immediately after you select the flights and .bomb verifies that you're not violating minimum connection times, etc.), but beyond that it errors out. I have successfully called the web support number (listed in the error message) and managed to ticket the run.

I've heard that sometimes people can book multi-segment runs on UA via Expedia but have never tried that myself.