We were heading to Chicago so I could speak at the 20SB Summit, & we were both really excited. I’d never been to Chicago before, & really had no idea what to expect. My only references were Home Alone (yep!) & the lyrics from Say Shh by Atmosphere:

“I love New York & Cali, but I ain’t movin’ — too overpopulated, saturated with humans. & I’m not big on rappers, actors or models… If I had to dip, I’d probably skip to Chicago!”

So you can only imagine my delight when Chicago turned out to be awesome. It is such a great town — we REALLY enjoyed ourselves, & I want to go back again soon!

Here’s a little run-down of some fun things we did. We were unfortunately only there for two days & one night, so we were definitely limited by time, but we made the most of it!

(Beware: This post is EXTREMELY photo-heavy! You might like to let it load while you make a cup of tea!)

“How was your flight?”
“Y’ever been on a plane before?”
“Yeah…”
“It was like that.”

… !

We disembarked at O’Hare & took a cab into the city to our hotel, Hotel Sax which we both LOVED! Our room was killer — two bathrooms, a living room, & a fantastic, huge bed. Here’s a photo I took of Chloe jumping on it!

We were put in a Studio King suite, which is a crazy 800 square feet (!!!), & it kind of made us wish we were a little more raucous… Two (relatively) well-behaved Earth signs aren’t really capable of making the most of a suite like that! Oh well. The room was great, very bachelor pad chic, with snakeskin armchairs & a padded leather headboard.

Everyone who worked there was supremely helpful & sweet to us — it couldn’t have been better, really. I recommend the Hotel Sax very, very highly!

A blogger’s work is never done…

The hotel is smack-bang in the middle of downtown Chicago, surrounded by bridges, & that super-famous Chicago Theatre sign is just down the block! The location meant we could easily walk a few minutes & make it to the Metro, which we explored excitedly!

We arrived in Chicago at about 10.30am, & after getting to our hotel & freshening up, made our way into the city to see what we could see. Our first stop? Intelligentsia.

At Intelligentsia. I clearly woke up at 5.30am! Disheveled chic!

After typing “vintage clothing” into Yelp on my phone, we decided that we should go to Wicker Park. We found a Metro station & took the blue line to Damon. It was around this time that I learned Chloe is an incredible navigator! She had been to Wicker Park maybe ONCE before, about five years ago, & has some kind of in-built compass which didn’t steer us wrong once! So we started to explore…

Quimby’s!

Our first stop was Quimby’s. It looks like your standard independent bookstore from the outside, but is even better on the inside! They have a massive zine collection which stretches throughout the entire store, & best of all, a black & white photobooth machine in the back!

Quimby’s reminded me about my zine lust when I was in my teens & early twenties. This girl I knew, Moira, ran a distro called Moon Rocket, & I would pore over her online catalogue feverishly before ordering a stack of zines. She’d send them to me in a big package, & I’d sit on the floor of my bedroom & read, loving that everything had been made & stapled by hand. I always wanted to start my own zine, but never got around to it. The internet took over, & the rest is history… But it reinvigorated my desire to get my hands dirty & create something tangible…

(Total aside: Moira has since founded Alphabet City, an art space & gallery, in Auckland, & I really want to visit when I’m there! They have a letter-writing club!)

Wicker Park is absolutely packed with vintage clothing shops, record stores, cute cafes & odd little gift shops. It’s so much fun, I really loved it — it felt like a cross between the best parts of L.A. & New York, but without any pretension or attitude. People in Chicago seemed really laid-back & chilled out, which makes for such a nice change from NYC!

One of our favourite places we found was a shop called The Boring Store. You walk inside & are faced with a wall of security cameras…

Inside, they sell spy supplies. There’s an installation of televisions & old video cameras. There are dance steps painted on the ceiling. It is FANTASTIC. There are things to marvel at at every turn, & as I walked around, I could feel the same wacky creativity I had as a child returning… I felt inspired & invigorated. When you step into that store, your brain is really encouraged to play!

One wall was covered in empty CD cases, & visitors were instructed to “Take Message, Leave Message”. I opened a case & found the following note:

!!!!!!!!!!!!! Needless to say, this made me really happy… I wrote a nice note in return. Hopefully it will make someone feel good.

The best part about this place is that The Boring Store is actually a front for 826CHI, a non-profit writing & tutoring centre for kids. Behind the store is an enormous classroom full of desks, where kids of all ages go after school & during the holidays to learn how to write, & also to get help with their schoolwork. I think this is so important & valuable, so I really recommend visiting The Boring Store & helping support their programs!

You could buy yourself an emergency bow-tie… Or some fancy googly glasses! Fun times!

Wicker Park also has some great street art & fancy walls. Viz!

Like my case? I bought it in an underground mall in Chinatown, NYC…

Double your pleasure! Chloe & I have matching iPhone covers… What creeps!

Wicker Park was great to walk around. There are plenty of interesting people, & plenty of ways to spend your dosh!

Perhaps a little bit too excited about this Garbage Pail Kids sticker!

We eventually made it back to the hotel room, & after an emergency mid-afternoon nap, Ben — that rad guy who films my videos! — came to our hotel room to take us out on the town. How nice! Ben is from Chicago originally so he was our tour guide for the night. We took a cab back to Wicker Park & took a seat outside at Big Star for amazing Mexican food! Their guacamole was incredible… Take it from someone who knows.

When we were done eating, we skipped across the road to The Violet Hour, a gorgeous bar, almost totally hidden behind a neon pink wall. Inside, it’s dark & beautiful, & they serve incredible drinks. I had an Austin 75 (Tito’s, Lemon, Hibiscus Syrup, Sparkling). Ben had a Juliet & Romeo (Beefeater, Mint, Cucumber, Rose Water) & Chloe had a mojito. They were all SO GOOD!

I have to give a huge shout out to Ben’s cousin, who is the best & organised our reservations! You are the best!

We wound down early & headed to bed to get rested for what would be a big day…

Ben!

At The Violet Hour… Photo by Ben Vogel!

Saturday’s first order of business was the 20SB Summit, & it was excellent! It was very well-organised & the attendees were sweet, curious & friendly. Since we were in Chicago, the city where they filmed High Fidelity, I decided to give my presentation in the format of Top 5 lists… It was really fun & I loved seeing everyone smiling back at me while I spoke!

…But when we walked out of my conference room at the 20SB Summit, you can only imagine our despair at witnessing a city that was now extremely DAMP! Yes, it had started raining, & Chicago rain means business! We quickly rushed across the road to the only place I could think of that would be dry: a mall. The Shops At Northbridge is pretty small, but this fact was redeemed by a visit to Candyality!

Candyality is a retro-styled candy shop with a huge selection that you can pick & mix together. The best part? When you take your bag of assorted treats up to the counter, they tell you your “candyality” — aka, they describe your personality based on what you’ve chosen! Such a cute idea.

To me, she said, “You chose a lot of milk chocolate, which means you’re kind, compassionate & empathetic. There’s some dark chocolate, which shows you’re sophisticated, chic & stylish. You chose some white chocolate, which means you’re a trendsetter. You picked a couple of vintage candies, which means you’re unconventional & like to do your own thing. You have some sour chewy candy, too, which means you’re a risk-taker.” Um… Pretty accurate!

Our enormous bags of sugar kept Chloe & I busy that day & all through the flight home. By the way, chocolate-covered gummy bears are a revelation!

After what seemed like an eternity, but was probably more like twenty minutes, the rain stopped, & we made our way to… The Bean!

The Bean is fantastic! It’s not really called “The Bean”, though… Its actual name is Cloud Gate, & it was designed by Anish Kapoor. It was said to have been inspired by mercury, & it reflects everything around it. I love it! It’s surrounded by tourists at all times, who are busy taking photos of themselves reflected in it… A sad commentary on our time, or simply natural curiousity? Whatever! We joined in!

This photo is me if I was a playing card. I’d want to be Queen of Hearts!

Jumping bean!

WHAT A CUTIE !

Looking slightly menacing, brandishing my umbrella…

After some major camwhoring at The Bean, we decided to go back to Wicker Park. Chloe bought some records at Reckless Records, & a couple of dresses at Buffalo Exchange. I tried on one dress before deciding I was feeling too lazy to shop (sacré bleu!), & so I took a seat in the changing room & ate chocolate-covered gummy bears!

When we checked our phones & saw we had a couple of hours before we had to leave for the airport, we decided to make a run to Kuma’s Corner, an epic & legendary burger joint in Avondale. Chloe had been raving about it even before we left NYC, so we definitely had to check it out!

Kuma’s Corner is a little pub where they blast metal all day & all the burgers are named after bands. The Pantera burger has roasted poblano peppers, bacon, cheddar & monterey jack cheese, homemade ranchero sauce & tortilla strips. The Slayer is a pile of fries topped with a 10 oz. burger, with chili, cherry peppers, andouille, onions, & jack cheese. The Led Zeppelin has pulled pork on it. The Neurosis includes horseradish mayo. You get the idea!

We pulled up in a taxi, only to be faced with a line of people waiting outside, & were told by the hostess that the wait for a table was two hours. Two hours?! We had to be at the airport by then! “Or,” she added, “You could wait by the bar & grab a seat as soon as it’s available, & just eat there.” No-brainer. We loitered by the bar for about five minutes, & sat down as soon as another couple left. Success! Burgers were ours!

Okay, so honestly: Service was slow. …Extremely slow. & by the time we were finished, our clothes stunk of smoke & charred meat. (Very Cavegirl.) But it was a great experience. The food was very good & the people-watching was sublime!

But as quickly as our trip had begun, it was over. Before we knew it, we were heading back to O’Hare for our flight home to New York City, looking at one another & asking, “Did we just go to Chicago?!”

Chicago is such a great town. I hope to be back really soon!

Clothing key: Wayfarer sunglasses by Ray-Ban. Pink tee by Betsey Johnson. Belt by Betsey Johnson. Black circle skirt, vintage. Dr Marten Darcie boots. Leopard-print watch by Betsey Johnson. // Turquoise dress, vintage. // Pink cut-out dress by Betsey Johnson. Black bolero from ASOS. Poppy pushlock satchel by Coach.

Photos by Chloe Rice… What a little beaut she is!