Chicago

Having only ever been to 390 (and numerous times over the years at that), it has my vote.

I second Elitis. If you only have one free night, Club 390 is hard to beat in the general area. Assuming you're staying somewhere in the vicinity of downtown Chicago, you're looking at only a 30-40 minute (worthwhile) commute each way. The only thing I'd advise is to not go too late (they're open until 5am and 6am some nights), because it's in The Heights, which can be a hit or miss area with regard to overall levels of sketchiness.

YMMV of course, but there have definitely been multiple weekend nights where I've left after 3AM and been perfectly fine. Just keep your wits about you as always.

Will also add that I've only ever been on a weeknight once or twice so if that or daytime is what you're looking at, there may be better options. I think (IIRC) the last time I did so, the dancer I was talking to mentioned either Wednesday or Thursday nights were pretty popular.

Probably Friday around 7pm ish give or take

Chicago is a horrible strip club city. It’s sad a city that large and beautiful doesn’t have good strip clubs. Damn shame.

Try Ricks

Club O was great, rip. Blackjack's is very meh for me and songs are short, especially if they have any specials. If it's just laps, Polekatz is probably best right now (tons of girls, many very hot). For a shot at extras, Atlantis and 390. Oh, and Rick's is ok at best and last I heard still gives air dances.

Can you touch at polekatz? I’ve seen mixed review

Yeah clubO was great back in the day

Yikes!

I've always been able to touch at Polekatz, granted, I don't go nearly as much as I used to. I've also seen people get warnings (nothing harsh). Just be discreet and let the girl lead.