Our Picks For The Best Night Out In Chicago

By Lisa White in Best Of on Apr 9, 2015 3:40PM

One perk of living in a major metropolitan city is it guarantees that you'll always be able to find something fun to do when heading out for the evening. But sometimes a bevy of options can be too much of a good thing. Making plans with friends can be tedious, leading to just another night spent at home after one too many response of "I don't care, what do you want to do?"

Thankfully our staff loves to share their favorite events to enjoy after dark. From drag shows to trivia, turtle races to taking in some fresh air on the beach, we share our favorite activities to enjoy after the sun goes down.

Tiki drinks at Three Dots and a Dash
Three Dots and a Dash is a tiki bar with a lot more to it than just tiny umbrellas in your drink. From an alley behind Bub City, descend down a staircase decked out with skulls illuminated in blue light. It's equally creepy and awesome at the same time. As soon as you enter you’ll no longer be in Chicago, instead arriving on a remote tropical island complete with a bamboo bar with a straw roof. It's just icing on the cake that they also make fantastic drinks. Considered to be one of the best bars in the world, Three Dots and a Dash is a spot that will definitely lead to a tropical best night out. — Ben Kramer

Three Dots and a Dash is located at 435 N. Clark St.

Karaoke at Alice’s Lounge
How can you beat a karaoke night where the DJ brings props, like inflatable guitars and saxophones, for your Wham! or Patsy Cline rendition? Alice’s Lounge truly hosts one of the best karaoke nights in the city. A perfect neighborhood watering hole, it's a laid-back bar with stiff cocktails and a good beer selection with the added bonus of complimentary snack mix to munch on throughout the night. The list of songs available to sing is impressive and diverse, so everyone in your group will find the perfect song to croon to way into the wee hours (they are open until 4 a.m.) The hilarious DJ participates with performers, giving it an edge over most karaoke spots in the city. Starting at 11 p.m. on Friday and Saturday nights, it's great late-night entertainment. I encourage everyone to give karaoke a shot, but it's as equally entertaining to just sit back and watch the performances unfold. — Carrie McGath

Alice’s Lounge is located at 3556 W. Belmont Ave.

Parlour Car Comedy at Bar Deville
Standup comedy is great. Free standup comedy is even better. Free standup comedy that’s actually good is the best of them all. You can find just that every Thursday night in Bar Deville’s comfy couch-filled back room starting at 9 p.m. Parlour Car comedy brings a rotating collection of Chicagoans to the stage each week and, to be honest, I’ve paid decent amounts of money to not laugh as much as I do when I go to Parlour Car. Bar Deville’s fantastic cocktails tend to put the night over the top.— Katie Karpowicz

Bar Deville is located at 701 N. Damen Ave.

Drag Matinee at Berlin Nightclub
Usually I’m more of a homebody than a party animal, but when I do go out I want to be surrounded by Chicago’s most glamorous and fabulous. That’s why I so often find myself at Berlin Nightclub. Berlin is always bringing something freaky to the table, whether it’s RuPaul’s Drag Race viewing parties, Madonna-Rama, Bowie Ball or, my personal favorite, their weekly Drag Matinee, which runs from 10:30 p.m. to midnight every Saturday. Berlin is strutting its way into their 30th year as a staple in Chicago’s gay nightlife, so you better believe they put on one hell of a drag show. The cover varies, depending on whether the performers are amateurs or world traveling acts. I’ve seen unforgettable performances that meld together Ursula’s “Poor Unfortunate Souls” from The Little Mermaid with Meredith Brooke's "Bitch." These ladies know how to work a room and the banter between host and performers is always a highlight. Once the show is over, the stage is open for the dancing crowd. So grab your favorite stilettos, disco ball-decorated bra top and your most Gaga-inspired hair-do and get ready to party down. — Erika Kubick

Berlin Nightclub is located at 954 W. Belmont Ave.

A DIY Tour of Chinatown
One of the best ways to really get to know our city is diving into a neighborhood and exploring. And although I enjoy Chinatown, one of my favorite neighborhoods, during the daytime, I really love spending a night out off the Cermak stop. First, stop by Phoenix and grab a dim sum snack, if you’re feeling adventurous try the curried baby octopus. Head a few doors down and grab some treats at the Chinatown Market (2121 S. Archer Ave.) before they close at 8 p.m. They’ve got a wide selection of noodles, candy and even live proteins, it’s a far cry from your usual Jewel trip. While near the plaza, satisfy your sweet tooth by picking and choosing a variety of candy options at Aji Ichiban. Walk over to Wentworth after and grab some baked goods at two of my favorite spots. Pick up some coconut and BBQ pork buns at Wan Shi Da bakery (2229 S. Wentworth Ave.) and then stop across the street and grab some Portuguese egg tarts at Chiu Quon bakery. Make sure to stop by the ATM, both bakeries are cash only and super cheap for delicious treats. Now that you’ve got snacks for later, grab dinner at one of your favorite spots (I’m partial to Lao Hunan or Go 4 Food) then afterwards sip some tea at Saint Alps (my go-to is coconut milk tea). If you are the type to enjoy karaoke, stop by Pop KTV, the recently opened and most sleek and modern lounge with plenty of large, private rooms for a whole bevy of friends to enjoy living out their inner rockstar dream. Chinatown excels at late-night dining, so stop by one of the popular spots that stay open until 2 a.m. or later, like Triple Crown, Chi Cafe (2160 S. Archer Ave.) and Sweet Station. And on your ride home, you’ve got those snacks from earlier to keep you company and soak up any beer from those rounds of karaoke. — Lisa White

Trivia at Parts and Labor
Trivia Night on Monday at Parts and Labor stands out among so many other trivia nights since prizes can be earned after every round (a rare thing), with the team in 1st place at the end of the night earning one epic prize. Sponsored by different beer companies each week (there have been Pabst, Schlitz and Revolution Brewing nights so far) with related prizes, including free rounds of beer and Parts and Labor gift cards, it is a great way to beat the Monday blues. The trivia rounds include general knowledge, sports, entertainment, bar life and more. The game starts promptly at 9 p.m., but I suggest getting there a bit early because they really pack them in for this incredibly fun and fiercely competitive trivia night. — Carrie McGath

Parts and Labor is located at 2700 N. Milwaukee Ave.

Turtle Racing at Big Joe’s
With a title like this, do I really even need to say more? Big Joe’s may seem like just your typical dive bar, that is until you witness the turtle races. Every drink you buy gets you a raffle ticket, those chosen are assigned a turtle and if your turtle is victorious you win a Big Joe’s t-shirt. Needless to say, when the challengers take to the starting line, the cheering gets fierce! Be sure to pick a race night and get there early, it fills up quickly. — Sophie Day

Big Joe’s is located at 1818 W. Foster Ave.

A Fried Fish Picnic in the Park
A few years ago, I bought a 1991 little red Honda Civic from someone I knew who was moving to Portland. It was the perfect kind of car to aimlessly drive around the city while listening to music during Chicago’s notoriously nice spring and summer nights. With the windows down and air brushing my face as I sped along Lake Shore Drive under the moonlit sky, I knew this city was home. The car died a few years later, it needed a new engine which made sense considering it was like 20 years old.

Sometimes I miss having a car and being able to drive whenever the craving hits. When I find myself feeling restless and wanting a night out on the town, I gather some friends, borrow a car from iGo and head north. My preferred plan is to stop at the Fish Keg. Fish Keg is a small, no frills fish fry joint in Rogers Park that serves well portioned cuts of fried fish at a fair price. Their building on Howard is adorned with a giant neon sign that literally says, “The Fish Keg” so you can't miss it. I usually grab a pound of catfish and glass of lemonade. Once I have my food, I head to Loyola Park, find a place near the water and enjoy the evening with friends.— Justin Freeman

Fish Keg is located at 2233 Howard St. and Loyola Park is located at 1230 W. Greenleaf Ave.

Stefan Ponce & Friends at East Room
Chicago-born hip hop producer Stefan Ponce is behind one of the best new monthly parties to pop up around town in the past year. Held on the final Friday of every month, Stefan Ponce & Friends will make you dance. Rap throwbacks and current chart toppers make up the majority of the soundtrack and never fail to threaten East Room’s speaker system. Get there early or you’ll be stuck at the end of a line that wraps around the block. Oh yeah, who are the “Friends”? Past guest appearances have included Hannibal Buress, Chance The Rapper, Vic Mensa and Logic. — Katie Karpowicz

East Room is located at 2828 W. Medill Ave.

Building a Robot
It’s nerdy youth confessional time— I was a member of the robotics team during middle and high school when I was younger. Learning how things work and making cool stuff is awesome in general, even more so when you are a young kid bored in Indiana. And robots? Always awesome unless they are evil. Thankfully Chicago has a way to live out your mad scientist fantasy at the Robot City Workshop. They have classes for all levels but my favorite offering is their Robot Date Night. Because why not build a robot while also building love? The after hours BYOB event for adults lets you choose from 12 different robot kits to build with your object of affection. During the event they screen robot-themed movies and their adorable Omnibot 2000 delivers popcorn to you and your date. The evening ends with a round of robot movie trivia as well. Cost is $25 per person ($50 per couple) plus the cost of robot kits and batteries, which overall is cheaper than most date options in this town. And with this activity, you get to keep a robot! Robot Date Night is a Thursday, Friday and Saturday affair and you must call and reserve your spot. — Lisa White

Robot City Workshop is located at 3226 N. Sheffield Ave.

Ending up at the Lake
A night in Chicago can take you many places, of course, but still near and dear to me, and surely to every Chicagoan, after all these years is the singular defining factor of the Third Coast. It’s increasingly arduous as one ages to live through a night of revelry long enough to see the sun rise, but it's worth the intoxicating reward. In what other non-coastal city can one watch the sun skip over the horizon from a sandy beach? Even under the guise of darkness, the serenity of Lake Michigan’s mini-waves pulsing against the shoreline (hopefully gently, rhythmically for this particular scene) brings you back home. This is why we live here. — Kristine Sherred

The Lake is located to the East.

Enjoying the best night by going out on a weekday
I’ve not a fan of waiting in a line, I loathed amusement park waits as a child and as an adult the velvet rope scene has never been my style. And if I’m quoted a 2+ hour wait at a restaurant, odds are I’m heading home into the arms of GrubHub and Netflix. While I love my nights in, I still want to feel like a social, functioning human so I’ve long been on a crusade to convert my friends to the joys of the weeknight out. First off, most weeknights out have an end time since you still work the next day. The pressure is gone to keep partying until the sun rises. Second, you’re already alert from keeping busy at work, so ride that adrenaline and keep your Saturday all to yourself and relax. And last, and most importantly, you can visit amazing places (some even with specials!) all while avoiding crowds. Have you waited in line to get into Violet Hour, given up hope on grabbing a table at Longman & Eagle on a Saturday night or spent too much time trying to rush and grab some elbow room at one of the many crowded bars around town? Not I, because I’m there on a weeknight (and honestly, I avoid Friday night, too). So stay indoors next weekend and maybe I’ll see you out and about creating one memorable Monday night. — Lisa White