Best Bar Nightclubs and Entertainment in Chicago

Chicago has come a long way from being a post-shift, whiskey-and-beer town. These days, the city’s bar scene thrives with creative bartenders and mixologists experimenting with ingredients, techniques, and philosophies. Whether seeking out austere, polished classics in the Loop or heading to Logan Square—where new cocktail dens open regularly—for playful tiki drinks, there’s something for everyone. Just want that beer and a shot? No problem, that’s still an option. Below is our list of top Chicago’s best bar nightclubs:

Uptown underground

The Uptown Underground is one of Chicago’s favorite places for dancing, drinking, and people watching. It’s fun to dress to impress at this club in River North where you’ll move to beats dropped by a roster of internationally-known DJ’s. The Uptown Underground opened in February after some months of wrangling over its liquor license because of its desire to offer entertainment of the burlesque sort. But the Uptown Underground is very much up and running. The best known of its entertainment. Uptown Underground is a speakeasy-themed club in a warehouse-like space with a large main stage and intimate lounge.

The nightclub’s entertainment schedule is jam-packed six nights a week with all sorts of surprising, intriguing and provocative acts, but the flagship show is “The Kiss Kiss Cabaret,” a sort of burlesque/comedy/variety show that can feature stripteases, bawdy jokesters, bowling pin jugglers, balloon animal swallowers, pet monkeys and … almost anything. This 7,000-square foot entertainment venue features a 150-seat main stage theater and a 50-seat lounge hosting regular burlesque shows along with other retro performances including vaudeville, comedy, cabaret and magic acts…

Location – 4707 N Broadway, Chicago, IL 60640

Berlin Nightclub

Berlin is an indie dance party featuring live acts, theme nights and some of Chicago’s best DJs. Steps from the Belmont L stop, Berlin has been a gay destination with a very diverse crowd of gay, gay-curious and gay-loving individuals. Berlin is charged with inquisitive, pulsing energy. Truly one of the best people watching spots in the neighborhood, things really start jumping around 2 AM when other bars close.

Berlin is critically acclaimed as the “Best Dance Club in Chicago” from New City, Rolling Stone, & Spin Magazines. Best bets for a good night are Tuesdays when Chicago legend Ralphi Rosario takes the turntables and Fridays with DJ Greg Haus. Weekends find the bar turning heavily gay male after 2 AM, usually filtering in from Halsted.

While the website clearly states no roller skates or hoverboards, Berlin is a dress-code-free, high-energy Chicago nightlife staple. Open until 4 am most nights, the place is a non-stop party for droves of locals, with a host of live DJ’s, a variety of themed dance parties, and plenty of all-inclusive, super-freaky gender-bending drag shows. With a powerful belief in equality and great music, Berlin is a progressive, always-thrilling, exuberant weekend hang out.

Location – 954 West Belmont Ave, Chicago, IL 60657

Baton Show Lounge

A taste of Vegas in Chicago? Sure, why not. You might want to wear a little extra lipstick tonight if you hope to outshine the drag queens here. The Baton Show Lounge has been staging raucous performances for more than 45 years now, and bachelorettes go crazy for it. Expect large estrogen-filled groups hooting and hollering at the stage and service that’s fairly disinterested. Shows are Wednesday through Sunday at 8:30 and 10:30 pm, and 12:30 am.

Baton Show Lounge offers a wide variety of classic American dishes. Enjoy a refreshing beverage from the full bar at Baton Show Lounge. Be sure to swing by Baton Show Lounge for frequent performances from live DJs. Noisy crowds plus raging music creates a very loud environment at this restaurant. Prepare to face the crowds if you visit on the weekend — Friday and Saturday are Baton Show Lounge’s busiest days.

At Baton Show Lounge, you can find ample parking that is readily available any time of day. Hop on public transit if driving’s not your speed; accessible stops include Merchandise Mart (Brown, Purple), Grand-Red (Red), and Clark/Lake subway (Blue). Baton Show Lounge is a prime location for cyclists to park their bikes and enjoy a bite to eat.

Location – 436 North Clark Street, Chicago, IL 60654

Boystown (Lake View), Chicago

Whether you’re gay, lesbian, or a supporter you will most certainly enjoy yourself when you visit the historical Boystown/Lakeview neighborhood in Chicago. The moment you get there you will feel the eclectic energy drawing you in. Boystown, in fact, is the first officially recognized gay village within the United States making it a cultural focal point for the LGBT community.

At night is when the Boystown/Lakeview neighborhood really comes to life! One of the more popular clubs to visit is Hydrate. Every night there’s something exciting to see. The club hosts drag nights, topless men dancing, and live entertainment you’ll enjoy from beginning to end. Put your dancing shoes on and come out and mingle while having a great time. Hydrate is open 7 days a week until 4 am or later.

The small slice of East Lakeview that makes up Boystown packs in lots of bars and restaurants. Whether you’re looking for the best gay bars in the city or a quiet place to grab a craft beer or wine and cheese at a wine bar, here’s where to drink in Boystown:

Bar Pastoral

You can’t eat at Bar Pastoral if you’re lactose-intolerant, and you can’t eat there if you’re concerned about your fat intake. On this, there is no budging. At a restaurant opened by a cheese shop, cheese is not part of the experience—it is the experience. So you have to love the stuff. Bar Pastoral is a place for eating that rillettes, or salumi—anything you can slap on bread (and the bread here is very good, crusty and soft in all the right places).

It’s a place for drinking wine, and they make it easy to do so—half glasses are just $5, so you can. It’s a place for Camba’s impressive housemade English muffins, spread with soft quark cheese, orange marmalade and a small piece of crisp bacon.

Elixir Lounge

At this shoebox of a cocktail bar, the drinks are skillfully prepared, the crowd is kept to a minimum by the doorman, and the music never gets so loud that it drowns out your insights on Jean Genet. The clientele is mixed in age but not in gender, and everyone is on their best behavior, which makes it an altogether more sophisticated and adult experience than Elixir’s next-door sister, Hydrate.

Duke of Perth

You’ll never know how relaxing Celtic music can be until you spend an afternoon at this Scottish alehouse. Listen closely as you hang out on the serene outdoor patio, eating fish-and-chips (it’s all-you-can-eat on Wednesdays and Fridays) and drinking from one of the best Scotch whiskey lists in the city—soon you’ll be humming along.

The Drifter, Chicago

The Drifter is an intimate basement-level former speakeasy/cocktail bar with eccentric nightly entertainment and a tarot card-inspired cocktail menu. Located below the Green Door Tavern (which was an actual speakeasy during Prohibition), its burlesque shows goes down quick and dirty with no announcement and no advance warning on a small stage that makes it feel like the show is just for you. Members of the Chicago Starlets shake their stuff in between musicians and variety acts amidst charming, vintage décor.

Location – 676 N. Orleans St. Chicago, IL 60654

The Violet Hour

Chicago’s The Violet Hour – the name comes from TS Eliot’s The Wasteland is acclaimed with good reason. This place is far more than just another speakeasy-style bar, it’s an institution and one that needs to be experienced. There’s no sign outside, just a bulb above the door marking the entrance; the interior is dramatic, all gorgeous blue walls, velvet drapes, and crystal chandeliers. Candles flicker on tables and the sound of low, happy voices fills the room.

This is the Violet Hour, which is 2007 introduced speakeasy style and the nascent “cocktail culture” to this hard-drinking town. The service at the bar is impeccable. The bartenders truly take care of guests, spending time getting to know their palates so they can offer up just the right drink. A set of house rules no cell phones, no light beer, a request not to bring anyone with you who you wouldn’t take to your mother’s house for dinner – ensure the atmosphere is always civilized, allowing a welcome focus on conversation and, of course, the contents of your glass.

Location – 1520 N. Damen Ave at Pierce Ave. Chicago

Lite Nightclub

LITE offers Chicago the best in service and experience, distinguishing itself from the cookie-cutter nightclub. Located in the uber-trendy area, be treated to unrivaled service where every need is met. Nothing is too good for the guests of LITE. Elegance and luxury, the way it should be. Dress code strongly enforced. (No sports attire, gym shoes, baseball caps, logo t-shirts-Tims, Ladies no flats) Heck

It’s your party, Dress to Impress! Dress code restrictions are at the discretion of the Door Manager and pertain not merely to articles of clothing: but more importantly to style and execution. Dress code subject to change without prior notification. Dress code enforced at nightclub’s discretion. Recommendations Men – Dress Shoes, Blazer

Location – 215 W Ontario St, Chicago, IL 60654

Brando’s Speakeasy

Brandos Speakeasy, the Chicago Loop bar in the historic South Loop, is where everyone wants to be. Once you enter Brando’s Speakeasy, which is a landmark status building, you will be impressed and welcomed with the intimate, warm, feeling you get from the staff as well as the patrons. Nestled in the Loop, Brando’s aims to offer something for every crowd: martinis for the lounge set, Italian food for the snackers, karaoke for entertainers at heart, DJ dance parties for clubbers and drink specials for the frugal. Lounge tunes, old-school standards, and classic rock tunes fill the air during the week, and weekends lend themselves to plenty of dancing to house beats and Euro-club mixes.

Location – 343 S Dearborn St, Chicago, IL 60604

Reverie Nightclub

Reverie is both a bar and a restaurant. Different days call for different remedies, different dreams. Seal the business deal over lunch, catch up with your friends over dinner and cocktails, or melt away the week in our upstairs lounge. This Private roof deck in the heart of Downtown Chicago has everything one would need. The laser cut panel and custom radius bar base give this space dimension, with accent lighting and plenty of refreshments behind the bar, this is the place to be on a nice warm Chicago night

Location – 414 N Orleans St, Chicago, IL 60654

The Pink Monkey

There is no doubting that Pink Monkey is a popular venue and it has won several awards to prove it. They offer a decadent night out for men ‘on the town’ as well as a great location for birthday, bachelor and divorce parties. On Saturday nights you can expect bachelorette parties as the club sometimes runs a male revue. In fact, the clientele is generally of mixed gender as plenty of couples attend the club together.

The venue has private booths, an open lounge seating arrangement, and VIP areas. The stages and podiums are well-lit and offer everyone a great view to enjoy the topless dancing and entertainment. The venue is quite small with a maximum capacity of around 200 people but offers an intimate experience to enjoy the show. Seating is arranged more like a restaurant than a typical ‘seats at the front of the stage’ establishment. Overall, the Pink Monkey is a mellow gentleman’s club that offers the best nights on the weekends and can be a bit pricey.

Location – 750 S Clinton St, Chicago, IL 60607

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