Dive Bars in Downtown Chicago & Streeterville Near Luxury Apartment Buildings

When you’re looking for a quick place to drink that isn’t filled with pretentious people and $12 cocktails, a dive bar is your safest bet. Downtown Chicago has some of the best dive bars in the country, and here are ten of our favorites.

Nisei Lounge

This Wrigleyville dive bar will make you feel like you’re at home from the moment you walk in. Cubs fans who don’t want to deal with the drunks that invade Wrigleyville for every Chicago Cubs game see Nisei as a place where they can escape the crowds but remain in friendly, Cubs territory.

L&L Tavern

L&L Tavern is a tiny hole in the wall located in Chicago’s Lakeview neighborhood. L&L is as dive bar as dive bars get – a couple of chairs, cheap beers and no frills. It’s rumored that both Jeffrey Dahmer and John Wayne Gacy frequented the tavern during their respective crime sprees in the 1970s and 1980s.

Gold Star Bar

Gold Star Bar in Chicago’s Wicker Park neighborhood features free popcorn, free pool and a jukebox containing songs for everyone. If you’re the type of person who likes a $2 beer and good conversation, Gold Star Bar is your best bet.

Rossi’s

Sandwiched in between finance professionals and luxury apartment buildings in Streeterville resides Rossi’s, a cash-only dive bar that has been operating in downtown for a long time. The bartenders are friendly and you can purchase beer to go on your way out.

Rainbo Club

The Rainbo Club in Chicago’s Ukrainian Village neighborhood is a local favorite. Low, red lighting and a couple of pinball machines are just some of the good things Rainbo has for visitors. Steps away from bustling Division St. nightlife, Rainbo Club feels like a secret bar that only you and your friends know about – and you want to keep it that way.