Chicago perfected the art of delaying judgment. From the first liquor license after Prohibition to Capone's favorite booth, the continuance is granted nightly.
- 1 · The Cold Open
The Berghoff
When Prohibition ended, Chicago handed The Berghoff liquor license number one and the family still has it framed. Dortmunder beer, schnitzel the size of a plea deal, oak everywhere. Open the proceedings properly.
est. 1898 · lunch till evening · verified Jul 2026
- 2 · The Detour
Billy Goat Tavern
Under Michigan Avenue where the newspapermen hid from their editors. Royko held court here, the Cubs curse was allegedly born here, and the grill still barks cheezborger cheezborger. No fries, chips.
est. 1934 · day into night · verified Jul 2026
- 3 · The Anchor
Gene & Georgetti
Chicago's oldest steakhouse, under the L tracks since 1941, where Sinatra ate when he was in town and the waiters have opinions they will share. Order the bone-in strip and cross examine nobody.
est. 1941 · dinner · verified Jul 2026
- 4 · The Wildcard
Old Town Ale House
Roger Ebert called it the best bar in the world that he knew about. Scandalous paintings of politicians, a library in the corner, regulars who survived every era of Chicago. Cash, and courage.
est. 1958 · till 4am · verified Jul 2026
- 5 · The Last Call
Green Mill Cocktail Lounge
Capone's booth faces both doors, the tunnels below ran liquor, and the jazz has not stopped since 1907. The poetry slam was invented here on Sunday nights. The last set runs late; the continuance is granted.
est. 1907 · jazz till 4am · verified Jul 2026