I have a new condo lisitng in a highrise on Marine drive. It 's another good reason to bring attention to this type of lifestyle in Chicago for a modest budget.
When I have clients who want to live in Lakeview or on the lakefront for $200,000, I usually suggest several highrise buildings. I particularly like 3550 N Lake Shore Drive, 3660 N Lake Shore Drive and 4250 N Marine Drive. You can pick up a 900 sq/ft one bedroom condo in these full amenity buildings for $160,000 to $199,000 easily.
I suggest clients buy one of the cheapest in original condition they can find. Hire my contractor with a budget of 20K and you can get a new kitchen, bath, closets paint and air conditioners. A nicely updated, great looking unit can go for $175K on average (I'd rather pay $10-15K less and put in my own stuff). However, this is not for everyone. A finished home creates less worries and hassels.
So, have a budget of $200,000? The lakefront in a full amenity building on lake Michigan is hard to beat. With the lower entry price, you'll be able to afford the assessments of $350-$400 (which includes your heat, cable, fitness room, doorman, pool etc...). Garage parking generally rents for $150 bucks a month.