401 N Wabash (Trump Tower) is probably my favorite building to go up in Chicago this century, even with the tacky letters plastered on ~5 years after completion. I love how it rises dramatically from the river and how its curved edges catch the light. It's quite the blend of late 80s/90s postmodern vanity with more contemporary materials and form... a fitting addition to the city's "skyscraper museum" along the river. Doesn't hurt it was the precursor to the tallest building in the world, either.
NEMA Chicago is a solid contender, although less compelling from some angles.
view that captures both:
Honorable Mentions:
- One Chicago
- Aqua
- St. Regis
- The Row
- Legacy @ Millennium Park
- One Bennett Park
- RUSH University Medical Center (East Tower)
- The Godfrey Hotel
- WMS Boathouse
- Embry
- 300 N LaSalle