The Whirlaway Lounge is named for a horse that went on to win the Triple Crown, despite the odds stacked against him. A man was lucky enough to have bet his money on him, and went on to open the Whirlaway Lounge with his winnings. That was in 1980, and today it's still an unpretentious neighborhood dive bar. Though that may change with the onslaught of gentrification going on in the area, for now it's still a laid-back place where bartenders greet you by name, beer is cheap, and you can still hold a decent conversation over the music.
Get travel tips and any other information about Chicago through our tripguru amanda