Pearl Jam at Wrigley Field, 2016 - three plus hours of intensity, very tightly performed. One of my measures of a great concert is the enjoyment level of seeing unfamiliar material played. I probably didn't know about a third of the songs, but it didn't matter. Eddie Vedder's voice was in great shape, and Mike McCready's solos were fantastic as was Matt Cameron's drumming. The audience participation was a cherry on top. Good sound and the ballpark made a great backdrop, as did perfect weather.
2007 Eric Clapton Crossroads Guitar Festival, Toyota Park - Sunny day with almost universally great performances by the list of artists below with a great sound mix and nice weather. Enough said.
Derek Trucks Band with Susan Tedeschi
Eric Clapton (w/ Steve Winwood and Robbie Robertson)
Metallica, 1991, Rosemont Horizon - they were absolutely at the height of their live performance abilities as a band. Hetfield's voice had all of the bark but with more power then before, and Lars played not only all of the double-bass parts but added fills here and there that weren't on records. Three hours of bad-ass intensity playing their best material. While I still like them, their live performances took a steep decline since 2000. Lars is a lazy, sloppy "drummer" now who may as well have the same kit used by the Stray Cats. Other metal drummers of similar age can still rage - because they choose to. Hetfield's live vocals no longer have any bite. And while Robert Trujillo is a good bass player, his background vocals are pathetic and that stupid crab-walk thing he does looks beyond stupid.
Lollapalooza II, 1992, Alpine Valley, WI - back when Lolla was a touring festival - Pearl Jam's 1st tour of large venues supporting Ten, Soundgarden supporting Badmotorfinger, Ice Cube, Ministry and headlined by a still relevant Red Hot Chili Pepppers. PJ was the performer of the day IMO, with Soundgarden a close second. Eddie lowered himself from the pavilion overhang by a rope. Soundgarden was awesome in every way, and seeing Chris Cornell pull of his vocals live was something. 20+ years later with Audioslave, his voice was still incredible.
Bruce Springsteen and (the entire) E Street Band, United Center, 2007 - this was my only time seeing them. While a relatively short show for them at about 2:15, it was fantastically paced. It was also one of the last shows by Danny Federici, who passed from cancer about 6 months later. Our seats were in the third level of the cavernous UC, but the band's energy made it all the way upstairs. I feel fortunate to have witnesssed the entire band, and this show met all expectations.