So you're driving back to Chicago* from Northwest Indiana (or anywhere farther south or east) and so you're coming up 65. First off, to me it's well-worth the $3.50 for the Skyway** to not have to rub bumpers with all the trucks on 80***. And then, right after you've paid the toll, Google Maps, et al, would have you stay on 90 and then take 55 to Lake Shore Drive. Boo. Take the second exit to Stony Island Ave and take that to the Drive. It's the Chicago equivalent of taking a scenic byway instead of the highway. You're immediately in the city. Oh, my wonderful Chicago. You get the grand thoroughfare that is Stony Island, then wind your way through Jackson Park, pass the majestic Museum of Science and Industry, and then approach downtown with Lake Michigan just to your right. What could be better? And Google Maps agrees that it only adds five minutes to your trip. Earlier today we went an hour out of our way in Kentucky to take a scenic byway (and visit a distillery). This little bit of tourism in your own city will only cost you five minutes (and $4.30 or so).
* And you live on the northside reasonably near the lake. Like me. Look, this is all about me, anyway, so don't worry if this is a terrible route to your house, just share your awesome tip in the comments.
** Plus the 80¢ or whatever for the Indiana Toll Road part of 90.
*** Yes, even with all the weird construction on the Indiana Toll Road. Still better than trucks.