Originally Posted by pjhyett

I purchased a one-way SFO-ORD a while back and I was looking at purchasing the return ORD-SFO but I noticed it's the same price if I just purchase the roundtrip ORD-SFO-ORD tickets. Since I travel to Chicago often, I figured I could just pick a date in the future when the one-way ORD-SFO is cheaper and save a decent amount of money.

My question is, with the long duration between my ORD-SFO and SFO-ORD flights, is there any issue with booking trips while that itinerary is still happening? I'm guessing there isn't a problem doing this, but it just occurred to me that I've never done this.

Thanks in advance.