Chicago

I'd recommend the deep dish and some Jazz.

Become friends with Rosey Palm

In which part of Chicagoland will you be? Depending on the area, I like:
* south suburbs: Club 390 and Jimmy's; Arnie's for extras
* west side: surprising fun can be found at some bikini bars in Stone Park near Mannheim Rd and Lake St: Bobby's, Carl's, Louie's
* NW suburbs: Heavenly Bodies in Elk Grove Village; extras at Blackjack's in Elgin

The Chicago area is not great for strip clubs, but almost all of my 60+ visits to SCs there over the last 10-11 years have ended happily. The only extras have been BJs: one at Blackjack's, two at Arnie's, and three OTC from a Jimmy's girl.

Extras at 390 and Atlantis too but it's $$ and very girl dependent.

Try not to get shot.

Drive to Detroit.

Get your educational rocks off at The Field Museum, Shedd Aquarium and the Art Institute, which is is one of my favorite museums that I've ever been to (mainly because it has my absolute favorite painting: The Old Guitarist by Picasso).