The “Windy City” of Chicago, Illinois is the third most populous city in the United States, beat out only by Los Angeles and New York City. As you would expect from one of the three most populated metropolitan areas in the country, the city is brimming with culture and is home to a booming nightlife. Chicago may have a more working-class, less glamorous connotation than its cousins to the West and North, but don’t let that fool you; “the Chi” can hang with the best of them when it comes to the bar and club scene.
If you are looking for the hottest dance clubs in the Windy City, Smart Bar is going to be one of your best choices hands-down, featuring both top-notch resident DJs and a packed calendar year-round of the hottest national and international DJs and electronic artists. Berlin in Lakeview is another locals favorite, known for welcoming the straight and gay crowd alike. As long as you like to dance, know how to have a good time, and are down with OPP you should feel right at home at Berlin. Vision is what you would expect from a top nightclub in one of the biggest cities in the country, featuring multiple floors, an indoor waterfall, booming sound and pyrotechnic lighting, and famous touring DJs of the likes of DJ Tiesto and Armiin van Buuren.
Chicago has a rich musical history ranging from rock to blues to hip-hop to jazz. The city is an excellent vacation destination for the live music enthusiast, as there are a plethora of venues catering to all varieties of music lover. The Green Mill on North Broadway is a truly legendary venue with history ranging back to its days as a prohibition-era speakeasy and a frequent hangout for gangsters including Al Capone. For an authentic jazz experience in Chicago, look no further, the Green Mill is the place to be. According to legend, secret tunnels under the Green Mill lead to the basement of the Aragon Ballroom, another historic venue in Chicago where legendary alternative rock bands like Chicago’s own Smashing Pumpkins as well as Nirvana once performed. You might catch one of your favorite national acts at the Aragon any night of the week. Having been home to legendary blues pioneers such as Muddy Waters and Howlin’ Wolf, Chicago is known for its blues music. Check out Kingston Mines or B.L.U.E.S. on North Halsted Street in Lincoln Park, or visit Buddy Guy’s Legends, Rosa’s Lounge, or Lee’s Unleaded Blues for some of the most authentic live blues you will ever have the privilege to hear. Chicago is also known for its hip-hop culture, having been home to some of the top artists in the genre such as Common and Kanye West. Check out the Shrine, the Mid, the House of Blues, and the Beauty Bar’s events calendars for weekly hip-hop events and national touring acts.
If you are looking to check out the dive bar scene in Chicago, hit up the Mutiny in Logan Square for their signature 36 ounce beers and no-cover live music. Gambler’s in Albany Park is a quaint dive featuring classic video game machines, darts, and pool. You might also want to grab a few drinks at Chicago punk bar the Exit in Noble Square, the Liar’s Club in Lincoln Park, or Sidekicks, a karaoke-oriented bar in Irving Park.
For comedy in the Windy City, be sure to hit up Mick Napier’s Annoyance Theatre and Bar, a Chicago staple specializing in improv and sketch comedy for 20+ years. iO is a long-form improv club a half-block from Wrigley Field where comedic greats such as Mike Myers and the late Chris Farley once cut their teeth. Longtime Chicago stalwart Zanie’s, open since 1978, the Comedy Bar, located in Ontourage nightclub (offering shows on Friday and Saturday nights), and Chicago Underground Comedy in Roscoe Village are other great options for visitors looking for a laugh during their Chicago stay.
Due to Illinois’ restrictive laws when it comes to adult entertainment, Chicago does not have an abundance of strip clubs, and some either don’t serve alcohol or are topless only. Some of the better ones are located in the suburbs outside the city due to less restrictive regulations. However, there are still some solid options either in or outside of the city proper. VIP’s is a popular club due in part to its proximity to the most prominent neighborhoods for Chicago nightlife, so if you are out in the downtown area of Chicago and want an adult-oriented nightcap this might be your venue of choice. Hit up the The Pink Monkey for hot girls and cold drinks on a budget as the Monkey is a BYOB (bring your own bottle) club. Polekatz is a self-proclaimed “Vegas-style” gentleman’s club offering over 150 dancers, VIP and champagne rooms, a full bar, and full-contact dances. Although gentleman’s clubs are not necessarily Chicago’s strong suit, you should still be able to find some adult fun in and around the Windy City.
Gay nightlife in Chicago mainly centers around Boystown, a gay-friendly district located in the popular neighborhood of Lakeview. Hit up Roscoe’s, Hydrate (which features some high-profile resident DJs), or the aforementioned Berlin to dance the night away in Boystown. For a mellow outing at a low-key bar, check out Little Jim’s Tavern, Bobby Loves, or Wang’s. Boystown isn’t just for the boys either; Closet is a good lesbian bar catering mainly to women but welcoming to men as well. Depending on what you are looking for, you might also want to check out Buck’s Saloon or the North End (sports bars), leather bar Cellblock, video bar Sidetrack, or male dancer bar Lucky Horseshoe Lounge. As long as you are gay-friendly, there is a lot of fun to be had in Boystown. Although centered around gay culture, it is a very accepting neighborhood and some of the clubs (such as Berlin) draw a mixed crowd.
Whether you are in Chicago for business, pleasure, or a combination of the two, if you are looking for some fun after sundown, suitable venues for your evening pursuits abound. Be sure to pick up a Chicago Reader and see what events are going on during your Windy City stay, and above all else, be safe!