Chicago on a $10,000 Day

I’m sure you can imagine the shock and delight I felt when my celebrity friend Chloë invited me to join her for a quick romp in Chicago. She had never been there before, but I had. When I was 22, I spent some time in Chicago making out with cute art students, shooting off fireworks, picnicking at Lincoln Park, and vomiting from the best heroin I’d ever done in my life. Chicago was weirdly fun back then, and I was hoping it would be again. She and her brother Paul were asked to host/DJ at some cheesy party and the organizers were hooking them up with free hotel suites and flights. Chloë needed a trustworthy dance partner, and I rose to the occasion. Unfortunately we didn’t get to explore the dark underbelly of the Southside, but just like when I was 22, the alternative kids were fully there to represent. Over the course of 12 hours, we met lots of new people, some of them friends that we’ll cherish forever (forever meaning like, two to five years in the scene). We didn’t see new places, but I took a lot of pictures of us looking way cute. Chicago rules!

This is Chloe on the way to LaGuardia, busy talking to her publicist about, I guess, upcoming roles 'n' such. I asked her if she was bummed about not getting any certain roles and the only one that came to mine was Where the Wild Things Are.

We got picked up from O'Hare in a black BMW and, wow, will you look at all that legroom? I could give birth in the back of this car if I wanted to.

We ate at a steak house before the party. Little known fact: Chicago steaks are so good that the legendary Peter Luger restaurant in NYC actually gets their cuts sent in from here. Something about aging and smoking or whatever.

The dude with the green motif is called Yonni. He's a super nice guy who pretty much set up the whole trip. We got carted around in this Escalade and told the driver to pump up the jams, which he was happy to do. Chicago radio is really good!

I almost forgot that my friend was famous until we walked into the party and she gave me her bad and started striking poses. She said that when you get your picture taken, you should hold your arms away from your body, otherwise they look like ham hocks.

This is Chloe signing an autograph. I said, "Your life is really crazy," and she said, "You have no idea." Touche!

These were the PR girls who put the party together. I guess they thought I was Chloe's asistant, because anything I wanted, I got. They were all, "Do you need anything?" and I was all, "Actually, I'm really in the mood for three peeled plums served in a top hat."

Weird to see digital posters of my friend.

This girl, Liz, told us she was "THE party girl of Chicago."

This guy goes by the name of Limo Bob and his claim to fame is that he invented a limousine that looks like an airplane. Also, Jay-Z gave him a gold bracelet. He might be known in Chicago, we weren't sure.

This is Zack. We didn't know him but as soon as we got to Chicago we called all out NYC friends and asked them to put us in touch with the coolest dude in Chi-town. All text messages pointed to ZACK.

Me and Dan from Drag City. A stellar dude. He drives a blue Volvo and knows a lot about music.

Then this girl showed up. Dan pointed out that she looked like Squeakey Fromme. In a sea of walking Gap ads, we were siked to see this girl bring it. Liz said she was in a band with her, and they're called Party Vibe Pubic Hair, or something like that.

This is Elizabeth, the bass player from the Psychic Ills. She's pretty.

Wow, it feels really good to have $10,000 in cash fanned out in front of your face like you're Elton John.

The next morning we had brunch with our newfound Chicago peeps.

After another grueling first-class flight with warm nuts, US Weekly, and heated towelettes, it's time to smoke up and go home.

Thanks Chicago, we love ya!