If you can swing the commute of just over an hour from Naperville to a hotel in River North and then another hour in the morning to the Airport, that will give you a great feel for the City. And bonus if you can get a dusk or evening boat tour. I’ve stayed at the W on lakeshore drive, the Marriott Marquis in a high NE corner suite with city and lake views, and the Hotel Chicago (Autograph) by River North and they all had good views but weren’t cheap. The latter used to be the office complex part of the corncob buildings and is a block from the river and walking distance to some great restaurants. Neat hotel with a muted, contemporary vibe. Otherwise I’m crashing at my daughter’s 5th story walkup in Andersonville that I suspect is an old convent, which is a cool neighborhood vibe with lots of good old school cool restaurants and a shitload of lesbians. It really depends on the vibe you want. My wife spent her adolescence in Naperville so she loves going back to the old neighborhood.