Having been frequented by a variety of personalities and iconic names throughout its history, visiting here will make you feel apart of something larger than life. Discreetly located underneath the Canterbury Courts apartments, this is the place to go when you want to sing the night away. This piano bar in the Gold Coast proudly totes the third oldest liquor license in the city. Although it dates back to the ’20s, step inside this vibrantly decorated space and it’ll instantly feel timeless. This family business has worked for decades upon decades to provide top-notch, regional Italian eats, and has one of the most impressive collections of wine in the city to back it up. Treat yourself to not one – but three restaurants in a single, historic location. Italian Village Photo Credit: Italian Village
This breakfast diner is known throughout the world, having been visited by politicians, celebrities, and athletes alike, making it a staple among Chicago’s oldest restaurants. The level of hospitality provided at this place rivals none, and anyone who’s been there can attest! The second you walk in, you’ll feel like you’re dining with family, and it’s been that way for decades.
Today, it has a modern speakeasy downstairs called The Drifter, where you can experience what it may have been like to come here in the ’20s.
#HISTORIC GAY BARS CHICAGO CODE#
The name comes from its green door – a secret code that served as a beacon for anyone trying to get some of that giggle water. Green Door Tavern Photo Credit: Green Door Tavernīuilt shortly after the Fire, one of the city’s most well-known, long-standing establishments was one of the only wooden buildings left after a law was passed to prohibit them. An absolute staple in the Taylor Street area of Little Italy, it’s a true veteran of Chicago’s oldest restaurants, and the food will have you coming back for more, guaranteed. There’s something about Italian food that it just seems to taste better if it’s made with generations of family tradition behind it. Advertisement Pompei Photo Credit: Pompei