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Windy City Magazine
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Karaoke Bar

Sidekick’s

About

Sidekick’s Entertainment Lounge & Restaurant is a karaoke and darts bar at 4424 W Montrose Ave in Irving Park, between Kostner and Kenneth avenues. Karaoke runs seven days a week with no cover, on a raised stage in front of a large dance floor, and the song book holds thousands of titles. The kitchen turns out appetizers, pizza, hot and cold sandwiches, main plates and Chicago-style hot dogs.

What to know

  • Parking is free.
  • The bar takes cash only, according to The Infatuation.
  • Song requests go through an app, so a charged phone helps.
  • The Montrose station on the Blue Line and the 78 Montrose bus serve the block.
  • Time Out Chicago, The Infatuation and Do312 all included Sidekick’s in 2025 karaoke guides.

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