I have no fondness for the South loop. Tons of new high rise condos, but lacking in character
South Loop is most assuredly a work-in-progress. There are a lot of options currently primarily because of its greatest benefit--proximity (Grant Park, Loop, West Loop, Chinatown, Pilsen, Greektown, Maxwell St., etc. etc.) and a lot depends on where you wind up (22nd & Indiana? Polk & Dearborn?). If I were asked to pinpoint ground zero today it would probably be the corner of Wabash and Roosevelt (w its convenient CTA station right there and, perhaps, a nice little corner table in the Bongo Room while you figure it all out).
"The fork with two prongs is in use in northern Europe. In England, they’re armed with a steel trident, a fork with three prongs. In France we have a fork with four prongs; it’s the height of civilization." Eugene Briffault (1846)