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Saturday 31 October 2020
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My Chicago: What is the most entertaining bar in the city?

THE QUESTION: What is the most entertaining bar in the city?

 “Spy Bar in River North. It’s a swanky lounge that is unpretentious, but you can smell the money. The women are appropriately underdressed.”

— GEORGE M.

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“Debonair in Wicker Park. It’s the perfect place to grab a drink and dance all night. The DJs do some really sweet hip-hop/dance mixes, and it’s a lot of fun. And Monday nights are themed if you’re looking for some costume action.”

— TRISH GARCIA | ARTS & ARTISANS

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“I love Uncle Fatty’s Rum Resort. They have great cover bands, and the atmosphere makes you feel like you’re on a Caribbean vacation.”

— STACY M.

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“Crimson Lounge. It’s filled with beautiful people and full of energy and sexuality through its muted ambiance. Real eclectic place, but fun.”

— JEFFREY

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“The bar at Tavern on Rush is one of my favorites. The crowd is a mix of all ages, and the food is great. It is always bubbling, though not too loud to interrupt a conversation.”

— ROANA BAXTER | CONCIERGE AT THE DRAKE

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“Boston Blackies is great for burgers and $10 buckets on Monday and Tuesday. I like Small Bar too, with its food, great craft beer selection and outdoor patio.”

— KATIE B.

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“Juicy on Milwaukee Ave. is a phenomenal wine and cheese bar. The upstairs lounge is cozy with booth seating and a great DJ. It’s a trendy neighborhood bar without the pretension.”

— CHASSIDY WHITE | CONCIERGE AT THE HYATT REGENCY

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“The Tilted Kilt brings all the best elements of a good sports bar together. The scenery is great, and the beer, food and TVs aren’t bad either.

— SCOTT BIENIASZ

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