I Found a Reason to Love Chicago

It was inside my hotel.

A few weeks ago, I got a blind deal on a travel site and we stayed at the nicest hotel we’ve ever stayed at in Chicago. Like most other times I find myself in Chicago, I was there for an event on the Near West Side, but stayed a few blocks from Millennium Park at the Kimpton Gray Hotel.

I’ll preface this by saying… I’m not a huge lover of the Windy City. As a midwesterner, I’ve been making the 3-hour trip at least once a year for most of my life, and I just… haven’t found the thing that draws me in. I’m just not impressed. The vibe is weird. You couldn’t pay me to live there.

But this time, I found a reason to love the city: it was a hotel.

Since Josh is wristwatch-obsessed, we drove up to Chicago for the Wind Up Watch Fair, which is basically a trade show for microbrands and smaller to midsize makers.

I fell in love with a vintage Zodiac watch and lost my sense and almost bought this Sailor Moon Baby G watch. I don’t even really like Sailor Moon?

Other than pining over watches I don’t need and/or can’t have, there are a couple of things I wanted to do:

• Vintage shopping and/or antiquing

• Find a cool local coffee shop that I’ve never been to

• Same as above, but make it cocktails

• Eat something I can’t usually get at home

Here’s every spot I visited and my honest take:

FREE WINE? I’M THERE.

Our hotel had a free, limitless wine happy hour from 5-6 in the lobby!!! Excuse me?! Give me no other amenities and this one makes it all worth it. Also, look at the marble. Can you even believe!!!

As soon as we checked in, I started researching the history of the hotel. After all, my true favorite vacation pastime is ghost hunting.

DID YOU KNOW THAT YOU CAN GET GLUTEN FREE CHICAGO DEEP DISH PIZZA?

I was absolutely fucking delighted when my friend shared this app with me.

It’s practically a crime to be in Chicago and not have deep dish. Bless Find Me GF for finding me gf pizza. I ate it twice in 24 hours.

We were peopled-out so we delivered Lou Malnati’s individual deep dish pizzas to the hotel and watched Titanic in the giant bed. Mine had hot giardiniera. Thank you, Chicago.

Side note: I also watched Twilight, Old School, and Happy Gilmore. I had to force myself to go to bed. What is it about hotels?

Excuse this horrible picture, but trust me: it was great.

THE REALREAL

There were so many people that it made it uncomfortable to shop, but I did try on an awesome 90s Versace jacket that the cool Carrie Bradshaw would have worn (not the one on And Just Like That, pls).

HANDLEBAR

I truly do not go to Chicago without a visit to Handlebar, known for its awesome vegan and vegetarian options. But I was sad to see that the gluten free veg options are more limited. Bummer. I ordered Diablos with tofu instead of eggs and it didn’t disappoint me, but I really would die for that buffalo “chick” wrap. There is so much on the menu here that is extremely worth the trip, even if that was literally the only reason you went to Chicago.

KOKOROKOKO

Of all the vintage places we went to, this one by far had the best selection. Pricing could be considered to be a little steep on some of the items, but they were gems, and I did find an awesome gold label Victoria’s Secret nightgown that I’ve been wearing as a dress. When it’s a gem, it’s a gem, and I was happy to pay a little extra.

BUFFALO EXCHANGE

It was so unbearably hot in here that I couldn’t stand to stay and look around. Love to see it. Anyway, a Buffalo is a Buffalo.

BIG BUD PRESS

imo, it was not worth going out of the way for this. After seeing much hype about this in-person shop, I was excited to see it. Literally nothing was special about it. I was blown away by how not blown away I was. I was like… this is it? I know the brand is cool and I love the boiler suits, but many people have told me to go to this store in person. To see a rainbow of plain t-shirts. #cool

SECOND PIZZA

Before heading home on Sunday afternoon, we went to Chicago’s Pizza just south of Wrigleyville. My mistake, though, because I didn’t know it was a game day. Oops! We ordered a giant gluten free pizza to go and headed back to Indy after this. This was good, and they had gf focaccia and LOTS of other gf options, too, but Lou Malnati’s was better, tbh.