Chicago Nightlife Tips to Have a Positive Experience | Part 2

Updated: May 27

After more than a year of COVID restrictions, everyone is desperate to get back to the city for a night out. Here are some of the best things to look forward to when we can safely get back to the dance floor.


Top Places in Chicago for a Fun Night Out

As the third largest city in the US, Chicago’s nightlife scene is quite extensive. In the last post, we covered how to navigate dating in Chicago, as well as some fun ideas and places to try out. We’ll expand on all that Chicago has to offer in this post, and give you a breakdown of everything you need to know about nightlife in Chicago.

You can be rest assured that Chicago’s skyline sparkles at night, providing a beautiful backdrop for windy city nightlife at numerous quality bars, clubs and theatres. Chicago’s most famous nighttime show happens at Second City, the legendary comedy club that’s spawned countless Hollywood careers.

Live music is all over the city, including jazz and blues clubs. Some bars still have the speakeasy vibe of the Al Capone era, whereas others are chic and modern, on rooftops or in dance clubs where DJs are playing music till the sun comes up. If you’re looking for a fun night out, check out these great spots and activities:

Broadway shows

Chicago’s rich theatre scene is on par with that of even New York City. You can find ornate, century-old theaters in the downtown theatre district, each showing (at least pre-COVID) an extravagant Broadway production. Check out smaller theatres, such as Steppenwolf, Goodman, and Chicago Shakespeare, as well, as they are flushed with tremendous acting, singing, and playwriting talent. When shows are going on, check for some excellent half-price ticket deals, even at the last minute, but if you want to go to a popular show it is best to plan in advance.

The Underground Chicago

Celebrities visiting Chicago and local VIPs enjoy partying at this club, a popular spot for post-Lollapalooza or post-game afterparties. The bouncers are known to be a bit rough and discriminating, so be sure to bring your A-game attire when you walk in the unmarked basement entrance - collared shirts and jackets for men, cocktail attire for women. It’s strongly recommended to make a reservation for bottle or table service if you really want to make the most of your experience here.

Green Mill Cocktail Lounge

Gangsters such as Al Capone would frequent the Green Mill, a long, thin, dark jazz bar that hasn’t changed much since Prohibition. In fact, Capone’s favourite booth, next to the bar, is still in use! The speakeasy charm, along with wonderful live jazz performances, has made it a Chicago institution. It’s a good late, late night spot - open till 4am - for music or a stiff Old Fashioned. Sunday nights feature the long-running and always entertaining Uptown Poetry Slam.

Second City

Second City is a comic institution, serving as a springboard for the careers of many Hollywood stars, including the likes of Tina Fey, Bill Murray, and Steve Carell. There’s a good chance that the people you see perform here will eventually make their way onto the big screen. Order a local Revolution beer or a dark rum Dark Comedy cocktail, and then get ready for a dose of big laughs with scripted comedy routines on topical subjects, followed by free-wheeling, interactive improv comedy.

The Up Room

Chicago has seen quite an explosion of rooftop bars in the past few years, and one of the best is on top of the Robey Hotel in Wicker Park. Unlike some of the rooftop bars you’ll find downtown, the vibe here is down-to-earth, and you can count on great drinks and views. A flight of mezcals or a glass of California red wine pair well with the outdoor patio’s unobstructed skyline views and low sofa seating. There’s even cosy seating inside the building’s spire.

Best Bars and Clubs for Dancing in Chicago

In the 1980s, DJs Ron Hardy and Frankie Knuckles began spinning a new strain of disco music built from bass and drum machines in Chicago clubs, establishing the city as a hub of dance culture and the birthplace of house music. And while you may not be able to bust a move inside the most legendary Chicago nightclubs, a new crop of late-night destinations has come to the fold to make sure that the beat goes on. Whether it's the jam-packed season of summer music festivals or winter in Chicago, these dance clubs keep electronic acts and talented DJs onstage late into the night. If you're looking for spots with crowded dance floors and energetic soundtracks, here are some of the best nightclubs and dance clubs in Chicago (in addition to the aforementioned Underground, of course).


TAO Chicago is located by the city’s historic River North stone castle that dates back to the late 1800s. This nightclub opened its doors in 2018, letting guests into its spacious nightclub and restaurant hybrid space. TAO is a sight to behold, as it features a multi-level lounge, restaurant, and separate adjoining nightclub. Its two floors also contain four private dining rooms and a large bar. A grand staircase, which includes round banquettes and Chinese daybed-influenced sofas, connects TAO’s ground and lower level seating.

It has a capacity of 1,000+ and its nightclub can function as two separate rooms or one large one. At the periphery of the club, guests can find secluded booths where they can enjoy some take a break from dancing. When going to TAO, dress to impress as this venue is a celebrity hotspot and you might catch the likes of Kourtney Kardashian, Taraji P. Henson, or Chicago Cubs players inside.


Prysm is located in the Lincoln Park neighborhood just minutes outside of downtown Chicago. The club is known as one of Chicago’s top-rated hybrid venues and allows its guests to experience live music acts, private special events, and nightclub performances. The massive venue is 10,000 square feet and consists of three distinct spaces: the Main Room, the Mezzanine, and the Champagne Lounge, which is also known as No. 9 to its more regular patrons. The Main Room and Mezzanine feature EDM, while the Champagne Lounge typically has a hip hop DJ.

Offering a perfect blend of concierge service and incredible energy, PRYSM also has state-of-the-art sound and lighting, as well as a 20 square feet LED wall. With a total capacity of 850, PRYSM can host a range of group sizes, providing both intimate atmospheres for smaller groups, and a larger room experience for bigger events.


LiqrBox is a vibrant bar and lounge located in River North. Created by BDG Hospitality Group and 8 Hospitality in 2018, it boasts three-level 7,500 square foot space with an electric ambiance fueled by rhythmic lighting and a custom street-art inspired design. Guests are able to enjoy music from DJs and live entertainers playing top 40, hip-hop, and EDM music as they dance the night away. Liqrbox is best known for its iconic “adult” juice box cocktails.

The club’s whimsical food and drink menu brings back childhood classic dishes and beverages with a creative adult spin. Guests are able to enjoy elevated versions of nostalgic dishes like pizza rolls (the exterior is a crunchy wonton wrapper with three cheeses and Italian sausage), corn dogs (with shrimp rather than a Weiner sausage), and their own spin on lunch-ables (box-ables which feature a fancy selection of cheese and cured meats).

And even the way the drinks are prepared as served is unique - beverages are served up from convenience store-inspired drink dispensers and slot machines, and the aforementioned juice box cocktails speak for themselves.

Sound Bar

Another River North hot spot, Sound Bar is an upscale nightclub that revolutionizes Chicago nightlife by boasting style, luxury, and state-of-the-art technology. The club prides itself on having a variety of separate areas for its guests to enjoy themselves, including a total of nine bars and several levels of entertainment within its 20,000 square feet of space.

Sound Bar’s European, minimalist decor features flat screen monitors, laser lights, and floor-to-ceiling video projection walls that enable its clients to project audio-visual presentation throughout the club. Occasionally, guests can enjoy exciting performances from costumed dancers as they sip on some cocktails. The music never stops inside the club which (prior to COVID) has different guest DJs every weekend.

Joy District

Let’s continue with the River North theme, shall we? Whether you’re visiting Chicago from out of town or you’re a regular, you’ll be sure to find enjoyment at one of Chicago’s premier dance clubs, located on the second floor of Joy District’s multi-level dining and drinking structure. At the Joy District nightclub, patrons will be able to immerse themselves in the ultimate partying experience thanks to the venue’s roster of the hottest local DJs and spectacular bottle service. And Joy District is a dance party hotspot for local and visiting celebrities - it has seen special guest musical performances from artists such as Demi Lovato, Ludacris, Travis Scott, Louis The Child, and DJ Flosstradamus.

Innovative Nightlife: Brought to You by COVID

How is Chicago nightlife adapting to changing times and varying regulations? Innovation.

Auris Presents is a new independent event production company, founded by multiple Chicago music industry veterans. Auris - Latin for “ear” - will be a vehicle for “unique projects and experiences” involving the cooperation of nearly a dozen promoters, producers and venue owners from across the spectrum of Chicago’s nightlife scene.

Partners in the initiative include Nick Karounos (owner of Radius and Prysm, partner in Concord Music Hall and former partner in React and co-owner of The Mid) and Stuart Hackley, founder and operator of Loud Crowd and former senior talent buyer for Disco Donnie Presents. Managing Partners in Auris include Chicago nightlife legend John Curley (co-founder of Paradigm Presents, lead programmer at Spybar and promoter, DJ, and all around impresario for much of the last three decades) and Joe Quade, founder of BAM Creates. Rounding out the team are Carson Rhoads, Dom Brown, Mike Lang, Garrett Birch, and Joe Calderone.

Auris is planning what they’re calling “innovative, experiential and curated events” held at “unique locations.” “We’re looking outside of the box,” an Auris spokesman told 5 Mag in an interview. “The fan experience goes beyond four walls and you’ll see that from Auris. That’s all we can say now, but we have announcements coming soon that will give you a better idea.”

The Bottom Line

As you can see, if you know how to traverse the nightlife scene in Chicago, it can be an absolute blast. Be wary of commuting, plan out your evening, and be sure to check out some of the awesome spots that Chicago has to offer. And in the next post, we’ll dive into what you need to know about the Chicago fashion scene.

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