Personally, I would prefer to be closer or further South than Lakeview just knowing the area and what I prefer for neighborhoods. But it is definitely doable to Ohare if you live close to a bus route that goes direct to the blue line stop. I had a girlfriend for over a year in Wrigleyville, a block from Wrigley Field (which is a part of Lakeview area) so I was going to/from the airport from her place sometimes. It's a bit of a hassle and I never liked doing it.

You have two options, you can take the bus to the blue line, I took the Addison ave bus, to the Addison Blue line stop. Took about an 1:00-1:05, just depends if you get perfect timing on a bus/train or not. Annoying to have to ride the bus during rush hours though with luggage. Imagine a bus "packed" full of people going to/from work and you have to carry all your luggage on there. Train is the same but much easier than the bus.

Or you can ride the Red line into downtown and transfer to the Blue line. This takes a little longer. Maybe 1:10-1:15. I never really did this much. Red line doesn't run as often it seems and I would always just barely miss the other train leaving at the transfer and I would have to wait like 15 minutes to transfer.

If you are commuting for a line, twice a week, no big deal but Reserve though with a 2 hour call out. Makes a big difference to live closer. You "may" have to go in and back every day sometimes, plus with only 2 hours notice you aren't nearly as rushed and can handle a delay easier, if the train breaks or stops for 15-20 minutes (happens sometimes). If you have a car, disregard and it doesn't matter. Parking in Chicago without a reserved dedicated parking space is a nightmare though, just a warning.

Places I would avoid are living near the Blue line anywhere between ORD-Belmont stops. They aren't good areas. You have to go all the way to Logan Sq before it starts to get Ok, that area is transitioning to a better area, then it gets better as you get closer to the city, Damen, Division areas are really nice but more $$$, then the train goes underground into downtown $$$. My friends in Lakeview always had to come meet us further south, we never went up there much. It's not that it's "that" far, but for some reason most people just never want to take the trek up to Lakeview unless going to a Cubs game.. Outside of Wrigleyville bar areas, not that much going on up there. Lakeview is not a bad area, just more dead IMO, which is good for people who like that or maybe married. I guess (Boys-town) is in Lakeview also if you are into that kind of thing..