The Best Bars in Chicago's Logan Square

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Float to a faraway land inside Lost Lake. Banana leaf-print wallpaper and cocktails served in giant seashells send love notes from tropical paradise. The concept pays tribute to the world’s first tiki bar, Don the Beachcomber. Sophisticated sweet drinks top the menu, but don’t stop there. The kitchen serves up Polynesian-inspired dishes to keep the island vibes going. An authentic tribute with light-hearted ambiance has earned Lost Lake a James Beard Outstanding Bar Program semifinalist title four years in a row.

Everyone loves a good speakeasy, and Golden Teardrops delivers undiscovered verve. Hidden in the basement of Lonesome Rose, the small drinking den is beautifully arranged to evoke an air of secret sophistication. Try karaoke on Thursdays and spirit-forward cocktails that pack a punch. The dark and intimate atmosphere is a great spot for a post-dinner nightcap at one of Logan Square’s critically acclaimed restaurants.

A classy bar with a neighborhood feel, Billy Sunday is an ideal date night spot. The cozy pub atmosphere illuminated by candlelight has a bit of fun with bar snacks like puppy chow and cheese popcorn. Owner Matthias Merges had earned himself quite the reputation as a standout chef and restaurant owner before opening Billy Sunday in 2013. The place is named after a former White Sox player turned evangelist. The bar plays up its artsy side with lovely looking drinks and intimate monthly cocktail workshops.

If you’re trying to catch a sports game but don’t want to miss out on Chicago’s coveted patio season, this is the spot for you. HD televisions line the walls of the interior at The Moonlighter, while a spacious outdoor area charms with string lights and picnic tables. The concept is refreshingly improvized and characteristically Logan Square-esque; piña coladas chill on tap while an aroma of cheese curds wafts from the kitchen.

Blues music is woven into Chicago’s cultural framework, and there are a number of downtown lounges where you can see talented performers sing their hearts out. Less touristy than some of the other options, this neighborhood lounge spotlights performers singing both modern and classic blues. The owner opened Rosa’s as a tribute to South Side Chicago blues bars in the ’80s and named it after his mother. Still family-owned and operated today, this spot is the real deal.

Groove to Latin tunes sipping Caribbean spirits at this good vibe getaway. Situated on a corner flooded with natural light, Estereo exudes an urban tropic energy. The daily drink menu is displayed on a colorful sign that hangs on the wall, as one might see in a Mexican market. Taste test pisco from Peru or cachaça from Portugal, or just charge up for the dance floor with craft coffee served all day.

Part dive bar, part nightclub, there’s always something going down at this two-floor party den. Try your hand at Skee-Ball while drinking cheap beer, or head upstairs to enjoy a proper cocktail. Either way, don’t leave without breaking it down to whatever DJ is spinning on the dance floor in the back. Dimly lit by an ever-present red light, this lively late-night favorite will put you in a trance.

A backlit sign across the fridge reads “Fancy Cocktail Bar,” but there’s nothing fancy about Good Intentions. The owners grew up in Wisconsin and wanted to create a homely feel with no frills. Wood-paneled walls, checkered floors, and a signless entry with a basic backyard patio all lend a nostalgic charm to this place.

This article is an updated version of a story created by Matt Persson.