Brando's has been doing karaoke in the Loop since 2007, and at this point it's something of a Chicago institution. The setting inside the historic Fisher Building leans into the vintage aesthetic with red velvet curtains, dim lighting, and a soundtrack that runs through Sinatra and Dean Martin during the quiet hours before things get going.

The song library sits at over 300,000 tracks. If something isn't in the system, they can look it up and download it on the spot. Turns are managed through a smartphone app. Two rooms give people the option of either being in the thick of it or sitting in the adjacent cocktail lounge to watch without participating.

Happy hour runs 5 to 7pm and the deals are real. After 7:30 it gets packed, so arriving before then is worth doing if you actually want a seat and don't want to wait twenty minutes for a drink. Good for groups, great for birthdays, essentially perfect for anyone who's been building up courage to sing since 2007.