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I've flown the Chicago shoreline dozens of times. With O'hare and Midway nearby, it can be an intimidating bit of airspace. However, review of the terminal area chart reveals a lakefront transition can be done easily and safely. I like to pick an odd altitude, something like 1900 or 2200ft. but rarely higher than 2600ft.

My office is downtown, and I've landed at Meigs a number of times for the commute. Wheels-up to touchdown is only 15 minutes, but by the time I get to the airport, prefight, fly, and grab a cab to the office, I might as well take (my regular) train. Anyway, have a look at a few shots below.
Chicago lakefront approaching from the southeast. Northbound along the Chicago lakeshore at 2200 ft. I'll fly between 1800 and 3000 feet to remain above Meigs traffic and under O'Hare airspace. As a point of reference, Lake Michigan is about 600ft. (above sea level).
Downtown Chicago view from over Navy Pier. Just passing the downtown area where the Chicago River cuts through the city. The artificial canyons are almost surreal.
Downtown Chicago approaching from the north. Southbound along Lake Michigan approaching Chicago. With O'hare looming just 15 miles to the west, the airspace can be intimidating to those the first time through. The depth of the downtown area is breathtaking.