Scarlet Bar

As the name suggests, Second Story Bar is hidden away above a restaurant in the River North area of Chicago. This bar is dark and divey with an old school charm that has remained untouched by the upscale modernity of the street below. Inside a sketchy looking unmarked entrance, you'll find a perfectly friendly bar serving cheap drinks to a soundtrack of camp dance classics. This is a true hidden gem and a unique venue among its modern neighbours.

Meeting House Tavern is Andersonville's newest and most unique entertainment experience. This space offers multiple types of entertainment along with a rotating selection of cocktails, nightly drinks specials and regular themed nights. Alongside traditional pub and arcade games, Meeting House also offers a range of board games and video entertainment. Large communal tables and lounge spaces allow for big groups to hang out and play their favourite games or just have a drink with bar snacks and pizza.

Sidetrack is the biggest and one of the most popular gay bars in Chicago. It's a video bar with a large lounge, multiple fully stocked bars, and a rooftop deck (which is great for people watching) and attracts a mixed but slightly older gay crowd. Themed events range from dance and lip-sync parties to a Tony Awards Viewing Night, so no matter what kind of night you enjoy, you can have a great time here complete with legendary slushy cocktails.

Roscoe's Tavern in the heart of Boystown has been a leader of Chicago's nightlife and entertainment scene for over 30 years. It's a friendly neighbourhood bar where people of all identities come together and catch up over pool or a drink in the lovely outdoor spaces. Super friendly staff create a safe space for everyone to let go and have a great night of dancing, good food, and cocktails.

Bobby Love's is a gay karaoke bar in Boystown. During the day it's a neighbourhood bar that's home to loyal regulars enjoying a variety of specials that are on offer throughout the week. People pack into this tiny bar, especially on the weekends, to sing karaoke fuelled by strong drinks but throughout the week the jukebox is always playing great music as well.

The Kit Kat Lounge and Supper Club is a premier destination for every type of occasion and every demographic. An imaginative and extensive cocktail list coupled with upscale contemporary cuisine makes for a super stylish night in even more stylish surroundings. Entertainment is provided by world famous drag queens, and Kit Kat Lounge is known across the country as a destination for a memorable meal and night out.