icymi, Chicago is not my favorite place to visit. I know people love it! Being from Indiana, I know so many people aspire to live there! But honestly, its charm has been lost on me—I sometimes catch a glimmer of it, but every time I leave Chicago, I come away thinking, you couldn’t pay me to live here.
This summer brought back-to-back Chicago trips, though, and both were admittedly amazing trips! A few weeks ago, I wrote about my trip with Josh to attend an event in Chicago. I’d made it my mission to find the best gluten free deep dish, and I succeeded.
I Found a Reason to Love Chicago
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.
LOLLAPALOOZA
Two weeks later, I went to Chicago for Lanapalooza—I mean, Lollapalooza—with my bestie, Hayley.


This had been a trip long anticipated for us both, and we had a blast—our one and only plan was to see Lana Del Rey in Grant Park for Lalapalooza. Despite being die-hard Lana stans, neither of us had seen her live before, and it was my first festival ever. To say seeing Lana was a magical experience would be an understatement.




There were a few other glimmers, too. We loved our hotel, we had an awesome adventurous Japanese lunch, and we found a coffee shop that puts gold in its drinks (if you ask for it. You don’t have to have gold, but why wouldn’t you?).
THE HOTEL: HILTON GARDEN INN MAGNIFICENT MILE
We really didn’t spend much time in the hotel aside from getting ready and sleeping. In hindsight, I wish I’d gotten up earlier and lounged by the pool. We put our feet in the water for a while before leaving, and it was necessary after my feet were absolutely obliterated by the boots I wore to the festival.
We stayed at the Hilton Garden Inn at the Magnificent Mile. It was not all that special, and there weren’t many amenities (aside from the pool), since it’s a business-class hotel. Still, for a quick stay, I’d do it again. It was cozy and the location was amazing. It didn’t blow me away like the Kimpton Gray but then again, that’s a 4-star hotel 😂
LUNCH: AN OSAKA OR HIROSHIMA STYLE OKONOMIYAKI
We had some time before we could check in to the hotel, so we stopped for lunch in the West Loop on our way into the belly of the beast that is Downtown Chicago.
We were thinking of going to Au Cheval, which Hayley loves, but there’s typically a wait and we were both dressed super casually (as you can see in our car selfie above). We were eager to get to the hotel as soon as we could check in.
In walks Gaijin. Picture this: it’s misty, slightly sprinkling, Hayley has just accomplished the incredible feat of parallel parking her Honda in the tiniest residential, streetside spot. We’re both looking at our phones, desperately trying to find a close spot to consume a quick food and leave. I look up and see the cute little inconspicuous sign for Gaijin.
We honestly didn’t really know what we were getting into, but this place was cool. We sat at the chef’s counter, where we could watch them splice together ingredients on the 12-foot griddle.
Okonomiyaki is a savory Japanese pancake griddled with your choice of ingredients. I ordered a Gaijin 75 because I’m very much a French 75 girly. Hayley got a 0 abv Hibiscus Fizz. For food, I watched the chef whip up the Vegetable Osaka style, which is gluten free.
To be perfectly honest, I’m not that adventurous when it comes to Japanese or Korean food, because I’m strictly vegetarian and I’m always nervous there’s something in the food that I shouldn’t be eating. This was good, though! Not my favorite, but I would do it again.
We both would recommend this experience if you’re feeling adventurous!



COFFEE: GODDESS & THE BAKER
Please for the love of all that is holy, go and drink a gold latte! We are legally required to get espresso. We did meet working at Monon Coffee, after all! Once we checked out of the hotel, we stopped at Goddess and the Baker on Wabash.
I had an apple oat latte WITH GOLD GLITTER. I cannot stress this enough. It was sparkly! They’ll put gold in everything. I’m a gold bitch and I’m *manifesting* so of course, I had to have it. The pictures do not do it justice.


THE TAKEAWAY: STAY DOWNTOWN?
Once again I had a lovely quick trip to Chicago. I think the trick is staying downtown (or in the neighborhood you’re exploring in). It’s not the easiest city to get around, even with the L trains. I seem to have the best time when I start in the area where I’m trying to hang out and stay there.
I feel like the charm of Chicago for a visitor is its history and in part, the architecture. If you’ve never been to Chicago, create your itinerary based on the neighborhood you want to be in, and don’t try to do it all. If you want to go to the museums or the theater, the Magnificent Mile is your bestie.