Bossip Video

ComplexCon Chicago 2019

Source: Complex

Bossip Be Trippin’: ComplexCon Chicago 2019

Beautiful people, it’s your fave airport-hopping adventurer Alejandro back with an essential recap of delicious clout buffet–the internet in real life–ComplexCon Chicago where I met wavy somebodies, vibed with transcendent tastemakers (shouts to my dad Bun B), witnessed swaggy strangers blow rent money on exclusive releases and maybe (probably) met my future wife in a shared Lyft.

(#LyftBae, if you’re reading this I’m taking you out for extravagant, life-changing, credit score-raising tacos–shark, swordfish, swanky salmon from wealthy waters (with a decadent drizzle of Cilantro, of course). You’ll never have a taste for peasantly poor fish tacos again)

But, seriously, I genuinely enjoyed my first time in Chicago–the weather, the midwest energy, the delicious eats, the gorgeous women, everything–all of it–was amazing, especially my first authentic deep dish pizza from the world-famous Lou Malnati’s. Bruh, MOUF SECKS.

My only complaint, though, was the TWO HOUR wait in the crowded eatery. Pro tip: Order in advance–wayyy in advance–to avoid waiting in a line that’s always longer than forever.

Now, on to ComplexCon that popped with larger-than-life activations, random celebrity pop-ups, cool people doing (and selling and giving away) cool things, a whole entire section of critically-acclaimed eateries (HAROLD’s!) and friendly clout fiends from all over the world.

ComplexCon Chicago

Source: Alex Ford/iOne

And yes, they were selling $5,000 24K gold-dipped burgers with an icy grill on the side (because fries are for poors, apparently).

For two days, I wandered around unsupervised and partook in super fun shenanigans. Brisk had a very dope “Hobbs & Shaw”-themed experience where you could film fight scenes with friends and meet WWE superstar Roman Reigns.

Jack Honey shined with its wonderfully rustic experience that showcased custom designed shoes by the world-renown Shoe Surgeon.

PUMA dazzled the crowd with its planet-sized basketball world and connected me with rising star Dreezy for a great interview.

Comedy Central caught eyes with a clever Rent-A-Center-themed activation with the hilarious cast of hit show “South Side.” Check out my spectacular Day 1 recap below:

On Day 2, I started strong with a magnificent 5-course meal curated by Uber Eats & Fat Rice. At one point, Bun B came over to shake my hand (I think he thought I was Brian Tyree Henry) while Zaytoven ran through his countless hits.

The first course was watermelon with caviar, prawns, oyster, salmon, tequila and king crab paired with a scintillating Magnum 2012 Champagne Piollot. Yes, it was as delicious as it looks.

ComplexCon Chicago

Source: Alex Ford/iOne

Next stop was the hilariously filthy Four Loko activation that punched me in the face from across the convention center. It was sick, twisted and perfectly done. There were masked baddies, *whispers* private rooms (yes, those with the… mmhmm), dirty mags and incredible art design. I loved it.

ComplexCon Chicago

Source: Alex Ford/iOne

Also spotted Saweetie moving Icy units, took some cool flicks at the Toyota booth and rocked with my favorite scumbag ScHoolboy Q whose DOPE performance I captured below.

Standing on the shoulders of its big brother in Long Beach, ComplexCon Chicago exceeded my expectations while providing quality escapism from reality. There were small issues with the app and long lines but it was a successful launch in a new city.

ComplexCon Chicago

Source: Alex Ford/iOne

Special thanks to PUMA for showing so much love and inviting me to their exclusive after-party. Also gotta shout out Complex and Lauren and the Hustle & Co. team for taking care of me.

ComplexCon Chicago 2019

Source: ComplexCon

Btw I stayed in a $40/night Airbnb in the heart of south side Chicago–a very quiet and Uber-accessible corner of the supposed “war zone”–that’s close to downtown and Chicago Midway airport.


Source: Airbnb

Thanks for reading, follow me on IG (@alejandro_niglesias) and be on the lookout for my next BBT where I tell you all about my trip to Portland/Washington!


Bossip Comment Policy
Please read our Comment Policy before commenting.