The Windy City, known for being a behemoth of jazz, blues, and house music is home to some of the best entertainment venues in the world.

Top Picks for Entertainment in Chicago

Going out in Chi-town is like nothing else in the world. The Windy City, known for being a behemoth of jazz, blues, and house music is home to some of the best entertainment venues in the world. Combined with excellent bartenders, unique venues, and luxurious lounges, you’re sure to have the time of your life in that toddlin’ town. If you’re ready to party till the sun rises, sip Pink Ladies and listen to some of America’s best musicians, then you better start checking out flights to Chicago after going over this list of noteworthy clubs, lounges, and bars.

SmartBar Chicago

Bar SceneSmartBar can only be described as Chicago’s Mecca of EDM. The club frequently hosts some of the best DJs in the local underground electronic scene like Derrick Carter, Michael Serafini and Justin Long. SmartBar boasts an impressive Funktion-One sound system that delivers crisp, deep, and bassy melodies and beats. The club is known for being low-key and well-maintained, with ventilation systems and fans making sure that those who were having a good time can stay cool. The staff is friendly and accommodating and is a haven for those looking to spend the whole night listening to good tunes. A no-frills no-pretensions place, SmartBar is a Chi-city must-see.

House of Blues Chicago

For anyone in Chicago who is looking for good music, good food, and good times, then there’s no better place than House of Blues. Located in the historic Marina City complex on the Chicago River it is a multi-faceted and endlessly entertaining venue. Stacked with multiple stages, bars, balconies, and dancing space, you won’t need to go anywhere else to start or end the night. Food here is known to be reliably delicious and cheap. Not only are the bands who perform here known for being consistently outstanding, but House of Blues has the sound system to deliver a proper show. With five floors offering drinks and entertainment, quirky old-school decorations and high-quality customer service, there’s no better place to spend a first date or fun Friday evening.

Ready to enjoy the night life of the Windy City? Better start comparing flights to Chicago! 


Chicago is known for pushing out some of the music industry’s most talented artists, producers, and DJs. Kanye West, Common, and Chief Keef – to name a few – all have their roots in the Jewel of the Midwest. And the likeliest place to find the next up-and-coming artist is at SpyBar. Hosting hot local DJs like Dustin Sheridan, Dabura, and Paul Johnson, SpyBar is constantly finding and delivering Chicago’s hottest talent. And they do it in the trendiest and coolest way possible. Though cover is usually $20, if you get there before 12:00 am you can skip the fee. With specialty nights focused on things like Latin music, hip-hop, and pop, there’s always a variety of talented musicians delivering the hottest and freshest beats from their genres.

Rosa’s Lounge

(Image via Flickr CC - Connie Ma)
(Image via Flickr CC – Connie Ma)

Hands down, the end-all be-all blues club in Chicago is Rosa’s Lounge. If you’re looking to have a genuine jazz and blues experience with some hometown warmth generated by a family-run business (because who wouldn’t?) then you can’t miss Rosa’s. Not only does Rosa’s family stick around the man the musicians and tables – making sure all of the customers are satisfied – but highly skilled bartenders are constantly serving delicious cocktails at a fair price. But be warned: Rosa’s isn’t for the faint-of-heart. It’s artists will bellow and belt it right into your soul. Overall, it’s hard to decide who steals the show: The decoration, the musicians, or the staff. Rest assured, you’re sure to have the show of your life.

Studio Paris

If you’re already an internationally revered and respected DJ then you’re likely to be found spinning sets at Chicago’s Studio Paris. The club has a reputation for being one of the best clubs in Chi-Town, and considering their all-star sets, it’s no wonder. Artists like Calvin Harris, Steve Aoki and Cee Lo Green have all graced the club’s stage. Celebrities are frequently spotted in Studio Paris, only adding to the mystique and excitement associated with the club-meets-lounge. If you’re looking to have your next best birthday, bachelor, or bachelorette party the club provides top-of-the-line bottle service. Paired with what was once Paris Club Bistro & Bar, now Il Porcellino, guests can fine dine and then head downstairs to finish off their night. But beware, all this glitz, fame, and glamor doesn’t come cheap.

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