When you think of the biggest festivals in the country, you think of Bonnaroo, Lollapalooza, Governors Ball, Austin City Limits, Coachella, Stagecoach, etc. I was actually at Gov Ball in June when I found out tickets came through for Lolla in August and I knew I had to go.

A guy I worked with in Seattle for years is now doing radio in Chicago and he and his wife are one of my favorite couples. They're dope, successful and travel a ton- basically my couples goals. I've visited them in Chicago once before since they moved there three years ago, and we'd talked about me coming to Lolla, but as usual, I didn't decide I was fully going or buy a ticket until six days out from leaving.

Lolla lineup this year was so good! The main artists I wanted to see were Childish Gambino and Meek Mill. There were plenty of other artists I wanted to see on the lineup like Ariana Grande, Twenty One Pilots, Lil Wayne, 6LACK, Janelle Monae and H.E.R., but I've already seen all of them and have never seen Childish or Meek! I had to go.

I missed the Thursday Lolla shows, and really don't regret it. Three days at any festival will wear you down, but four days at Lolla would have been hectic. The main stages are a full mile apart from each other, and there are up to 400,000 people attending, so getting from one stage to the other, walking that mile while dodging hundreds of thousands of people was pure chaos.


Friday at Lolla was dope. I wanted to make it there early for Tierra Whack, but time got away and I missed her and 21 Savage. I would have gone to Janelle Monae over Death Cab for Cutie, but we got insider info that Chance the Rapper was coming out during Death Cab's set to do their new collab off of his debut album, so we risked it all on Chance. And he showed up! I've never seen Chance before, and have had his album The Big Day on repeat, so seeing him perform was a nice added bonus.


I think I forgot to eat much and ended up unintentionally drunker than I expected to get. Not too drunk, but NF into Childish Gambino were a little bit of a blur. There was a fall at one point while dancing, and my left knee is still looking a bit wrecked. Bygones. It was a great night! We dipped out after Gambino and met up with a bunch of radio peeps for dinner. Friday at Lolla was perfection.


My friends I'm staying with live about a mile from Lake Michigan in an area called South Loop. Their neighborhood is gorgeous and I couldn't wait to run it! I woke up early on Saturday morning and did a 7ish mile run, which felt amazing and helped me sweat out a slight hangover.


My friend Randi found the coolest pre-Lolla party for Saturday afternoon hosted at a hotel by Bed Head. It was the best pre-party I've ever been to. Hair bar, henna tattoo bar, glitter bar, real bar + a bunch of rotating female DJs who were all great. We spent like two hours there, got our hair did, got drunk and danced and got henna tattoos that I'm still regretting to this day. Is it known that nothing takes henna off except for time and shame? My XO collar bone tats have turned into smears and stains that now look more like prison tats than cute hugs and kisses. Ugh. So that's currently still happening.


The girls wanted to see a different show while 6LACK was on, and I could not miss him so I went dolo to his set. 6LACK is one of my most listened to artists. It's hard for me to say favorite outside of Drake and Frank Ocean, but a top five most listened to is just statistics, and 6LACK is in there. I've seen him twice (?) before but not since his last album East Atlanta Love Letter came out, so I loved hearing my fave songs from that album.


It's hard for me to say there's a more consistent performer in my life than Lil Wayne. I think Lolla was the 8th or 9th time I've seen Weezy, and every single time is incredible. He really puts it all on the stage. I've also never seen a crowd like this before. Lil Skies got out across the lawn right before Tunechi went on, so everyone from that set just basically turned around to face the T-Mobile stage. You can't see even 1/5th of the crowd in this picture. It had to be over 100,000 people watching this Wayne set, no lie. Incredible.


Not sure who a few of the people in this picture are, but the city of Chicago looks amazing in the background. This was before J Balvin and Twenty One Pilots sets.


Speaking of J Balvin, what a show! It was my first time seeing him and he brought out Daddy Yankee! Which, I wasn't fully aware of until a friend snapped back to my story and was tripping out that he came for Balvin's set. We stan a pop up guest appearance.

We went out with another group of radio friends that night and I used CBD oil/lotion for the first time on my wrecked shoulder, so it was quite the night.


Sunday morning, Randi and I went to a boxing class in her neighborhood and got ready for another day of exploring the city and Lolla! I was on a mission to get the henna tats off of my chest, but no luck. Even Ulta told me they didn't have a product to help speed up the process. Great.

We took a boat along the river into downtown and shopped around + had the slowest but most delicious lunch at True Foods before making it to the Lolla gates for Denzel Curry.

Except the lines were reckless. Two hour waits at two entrances after one entrance was shut down for fence jumpers. I had a media pass, so I could walk down a mile to the designated media entrance with no line, but the girls did not, so they opted out of waiting two hours to get in and I slid in with the media for Denzel and Meek Mill.


Meek's set was so hype! I've always been a Meek fan, so when he and Drake got into a feud when he was dating Nicki, I was actually sad. Obviously I had to side with Drake so I had to boycott anything Meek was doing until they made up. Thankfully that happened, and Meek put out what I think was a contender for album of the year last year. Meek was the best part of Sunday for me and I left before seeing Ari because the crowds were just way too extra.


I left to meet friends at a bar and stumbled upon the Bean. Such a pretty night!


Monday I had a day of no concerts and just city. I went for another long run, this time about nine miles, along the great lake and made it out to the navy pier which was gorgeous.


After taking the train into the city, I shopped around and bought things that I didn't have room in my luggage for before heading back to my friends to scoop up my luggage and take the train to O'Hare. But there was a problem. There's always a problem.

I left at 5:30p for a 7:30 flight. The train is only supposed to be 45 minutes, so I'd have a solid hour and 15 mins at the airport. Now anyone who knows me, knows I never give myself even an hour at the airport. So this was unusual for me. But my friends convinced me that sometimes the train delays, especially during rush hour, so I took their advice and gave myself plenty of time. I thought.

My train did delay, just like they said. Two times. Both for twenty minutes. And we're not talking, delayed at a stop. We're talking delayed in between stops, doors not opening, waiting for 'track clearance'. So at the final delay, I'm getting a little nervous. My 75 minutes is now looking like 35 minutes. No problem, I told myself, because I'm not checking a bag and I've peeped the TSA lines and there's literally a zero minute wait.

I get off the train finally and it's about a 7 minute walk to security inside. I don't fly United often, so I didn't realize that they have a policy for those not checking bags to check in at the kiosk to get your boarding pass. Now it's about 27 minutes before my flight. I get to the kiosk and another policy United has, is that you can't get a boarding pass from the kiosk if it's less than 30 minutes to your flight. Now they tell me I have to go to a counter and get my boarding pass. No line, but all of the three tellers at the counter had customers. It's now 7:08 for a 7:30 flight. And I've cut it close enough times to know that the gate closes 10 minutes before takeoff. So really I'm looking at a 7:20 window.

I wait 4 crucial minutes to get to a teller. It's now 7:12 and my cutoff is 7:20 to be at my gate. I frantically tell him that I just need my boarding pass, and will zip through security to my gate. He refuses. "It's too close, I'll have to call the gate and see if they'll let me." NO! Just call the gate while I get through security! Just give me a chance at least! He refused. He calls around different gates for another 6 minutes before finally getting ahold of my Boise gate, and now that it's 7:18 and the gate closes at 7:20, they've obviously not clearing me. United really f&$#ed me. United and the train, to be fair. But damn United, you couldn't even give me a chance?! I was not happy.

And naturally, that was the final flight to Boise. I tried everything. Can I layover in Seattle or Portland or Denver or Minneapolis or Phoenix or SLC? Where can I route through that will get me home tonight?! Nothing would get me anywhere until the next morning. Which was awful, because I knew that meant I was missing our show in the morning. Not really a best case scenario, and I lowkey got a little depressed over it.

I flew out the next morning, through Denver and then made it to the station in time for a news interview we had scheduled but felt terrible that I let something so dumb happen.

My takeaway? Give yourself extra time. This applies to so many areas of my life. I never want to miss anything and love to pack as much as possible into a short amount of time because I love life and experiencing as many things as possible! But, there are only 24 hours in a day regardless of how hard I try to fit more in, so I need to come down to earth and be more realistic with timing of things.

Note taken. Lesson learned. Trains and subways are flawed and I can't count on everything to go perfectly in order to make things happen the way I need them to. Plus United, your policies are bogus.

End of the day, Chicago is one of the coolest cities in the US in my opinion and Lollapalooza was incredible. 10/10 will be back!



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