I was just in Chicago to see Nick Cave & Warren Ellis.
Jazz bar - decent food but $$$. You need to reserve a table.
A dive bar - Grab a can from the fridge and take it to the bar to pay for it type of place - cash only btw - no frills.
Relevant to my needs…an English pub for a good roast on a Sunday. The Red Lion Pub
A DiS friendly bookshop Picked up a signed copy of Warren Ellis’ Nina Simone’s Gum
Big fan of the Art Institute of Chicago too
that should cover a few bases.