Just came across milepoint today, and love the site thus far! I'm CO Platinum and am at 57 Segments YTD. I've yet to ever go on a MR/SR, so this is new to me. I have a $200 & $50 credit from UA which I would like to apply (I don't think I can use it on CO operated flights)? I have December 5th-26th off. A few questions: 1. Does anyone have any good routes from ORD in mind? I'd prefer something on a A320 or greater (so I can try to at least do this as an upgrade). 2. Does it make sense to just book a RT with a connection both ways (4 segments) or a connection + 1 way? 3. Is it better to book via ITA Matrix or directly with UA? 4. I have plenty of hotel points, so does it make sense to do this in 1 day or 2 (which is cheaper)? I'm willing to spend ~$100 out-of-pocket to get a better route on larger equipment. However, if it's cheaper to go East vs. West from ORD (and possibly do it in 1 day), I wouldn't mind ERJ type aircraft to get it done faster. Any help would be awesome!