I know chicago isn't known for its pastrami, but there's a hidden spot in the french market underneath olgilvie station in the loop called fumare, and they have this montreal style pastrami that's incredible. best pastrami sandwich I've ever had. you pretty much have to go during lunch (around 11am) during the week since they sell out pretty fast. the aesthetic of the french market is pretty grand too.
then there's harold's chicken... with one being right off of wabash in the loop. fuuuuuuck I might have to go tonight lol.
if you want one of the best burgers in chicago, there's au cheval and small cheval, but a lot of times the wait is 3 hours at au cheval since they don't take any reservations. an alternative burger spot would be the metal burger bar "lockdown" which is similar to kumas corner but better. $10-15 is kind of a lot for a burger from both places... but it's worth it.
the lagunitas brewery in Chicago is very aesthetically pleasing and anyone I bring there from out of town loves it. it closes at 9pm though since it's in a bad area.
from there go into wicker park which is like lincoln park/ lakeview/ wrigleyville without a lot of the cost/ congestion/ prices. However you will see neck beards and other forms of hipsters. Over there check out hot chocolate (great fancy bar and good hot cocoa, lol) and the blue line tap.
wicker park has/is changing to a more yuppy & bro crowd. when I moved out of the wicker area in October a lot of the bars were becoming overrun by the bro-type dudes with beer trolleys constantly passing through. still an awesome area though.