Butterfingers,
I hear you. I am moving to Chicago on Aug 1 from about 1000 miles away. I was apartment hunting from afar for about a month and lost out on three apartments because they just turned over faster than the realtor could send me the photos. I was immensely frustrated. About two weeks ago (six weeks before my move-in date), I flew out for 48 hours, viewed 14 apartments and picked one. It was exhausting, but it worked. I love my new place and I had everything squared away six weeks before the move in date.
I made my appointments from about a week ahead of time for my favorite places (though a couple of those rented before I got there) up until I was boarding the plane in Boston to fly out to Chicago. I also kept checking the listings while I was there and scheduled viewings for a few places almost on the spot. It's absolutely one of the most stressful things I have done. And I've been apartment hunting in Boston a half dozen times in the last ten years. Chicago is just something different altogether. But it is possible. I saw a number of listings for Sept 1 in the neighborhood I'm moving to, but it might not be the same part of the city as you. I'd definitely say to pick more than 3 or 4. I had 4 top choices, three of which were great from the descriptions and photos and utterly disgusting in person. 14 was probably too many, but I figured if I was there, I may as well just spend the time looking at everything within my price range and move-in date.
Good luck!