What is the timeframe for these two races? Your safest bet may be to register for both, if advanced registration is necessary, and see how the conditions are for the first.
While my history at Lakefront is, to say the least, unpleasant when it comes to the wind, I would not say that my experiences reflect the typical year. Remember, getting a headwind on a point to point nearly straight shot course like Lakefront requires the wind to be out of the right (wrong) direction. Get a wind out of the north and you'd have a nice tailwind to carry you through those final miles. From what I've heard and observed on years I was not running, you are more likely to catch a tailwind than a headwind at Lakefront.
FWIW, I won't be running Lakefront this year so your chances of avoiding a headwind are that much better. 😉