5 of the Best Entertainment Destinations in Chicago


Image via Flickr by Jamie McCaffrey

Chicago is one of America’s most iconic cities. Its rich history, bustling nightlife, and cultural heritage make the Windy City an enchanting travel destination. If you’re looking to see what this town really has to offer, check out our list of the top 5 best entertainment destinations in Chi-Town.

Jazz and Blues


Image via Flickr by Aaron Warren

Buddy Guy’s Legends is nestled in the heart of Chicago’s jazz and blues South Loop. Founded by Buddy Guy in 1989, this venue features some up-and-coming artists as well as the most famous legends of blues, including Stevie Ray Vaughan, Lou Rawls, and BB King. The venue is filled with classic jazz memorabilia including instruments and awards won by the greatest pickers and players of our time.

Punk Explosion

Reggies is just a few steps away from Buddy Guy’s and offers a wide array of pure, unadulterated punk, metal, and rock music. Downstairs, you can peruse the old school record shop, but once the lights go down in Chi-Town, Reggies becomes a rip-roaring explosion of thrashed-up metal goodness.

Old School, New School


Image via Flickr by M. Jeremy Goldman

The Double Door is a surprisingly quaint club, but don’t let its appearance fool you. This venue has hosted the likes of the Rolling Stones and Smashing Pumpkins for amazing impromptu shows. New bands and old Chicago standbys alike haunt the DD clubhouse, but the best part of the Double Door is you never know who may show up to play the next set.

Dance Club Fever

You never know when heading out to go clubbing in a new city – any location can be a complete hit or terrible miss. If you’re looking for a winner, check out Dolphin. This LED-saturated dance venue features both local and international guest DJs that are guaranteed to get you moving.

Whether it’s house, techno, or dubstep, the Smart Bar is one of the best spots in Chicago to get your fix. At one time, this club hosted some of the best grunge bands in the city. After a complete makeover, the Smart Bar features a true dance club atmosphere coupled with music spun by the city’s most well-known DJs.

Take in a Show


Image via Flickr by Bradford Timeline

If music clubs and venues aren’t your thing, Chicago’s theatre district will fit the bill for what you’ve been craving. Are you an avid fan of all things Johnny Cash? Book a show at the Apollo Theatre for Million Dollar Quartet. This musical is based on the famed 1956 recording that brought together rock and country legends Johnny Cash, Jerry Lee Lewis, Carl Perkins, and Elvis Presley.

Chicago’s Music Box Theatre is the perfect place to come in from the cold and catch a cult classic. Rated 4.5 in the Gogobot Chicago travel guide, this theatre is charming and cozy. In October, the Music Box Theatre features a spooky 24-hr horror film festival that is certain to raise your spirits.

However you plan your next trip to Chicago, the Windy City is sure to capture your heart. Chicago’s old-world charm and new-school edginess offer something for everyone to enjoy.