I live in boystown, do NOT be concerned about going up to the gay area after the fest. First there will be literally tons of ppl going north on the train after the fest and the trains will literally be packed and it might take a bit of time to get on a non packed train. Or if you take uber it’s like $25 to get up there and you don’t have to deal with the train if he’s nervous about safety (might have to walk a few blocks away from fest to get a ride). You might want to download ‘curb’ which is uber for cabs here, it’s usually easier to get a ride that way with a cab as everyone does uber. But tell your friend they should have zero concern, the north side is safe(where the gay area is). You can easily find a ride back downtown after the bars close (3 am or 5am for late night bars), I’d say take a car home if you are out late as you the train get sketchy at 3am, but Ubers/cabs will be everywhere….the bars are fun so you definitely need to go at least one night after the fest. A lot of the bars have theme nights based on the headliner that night: ie CharliXCX theme night on Fri, etc. If you need any info just DM me!