How to Spend a Day in Wicker Park


Before my next three month Eurotrip I decided to take a trip to Chicago – a city I’ve been to probably about a trillion times and also a city I have never left the downtown. Gasp! Aren’t I a great travel blogger? Back when I was growing up in Indiana, I would take a trip to Chicago nearly every year, either for a field trip or family trip, or spontaneous trips like that one time I drove shoeless because I wanted to have a more comfortable drive, just to get to Chicago and realize I forgot to bring any shoes at all. As you see, Chicago and I have never really clicked, and I know this especially now in comparison to so many other big cities I have clicked with.
This time, passing through Chicago, I wanted to do anything except be downtown. I didn’t care about the Bean, the Loop, the Magnificent Mile, or the Willis Tower – which, by the way sorry, but that tower will always be the Sears Tower to me. So I scoped out Lincoln Park, Wicker Park, and Logan Square all on Google and five minutes after doing so, I found a subway stop named Damen and I was convinced it was a sign: Wicker Park, here I come.
After an oddly interesting train ride you can read all about that in the appropriately named post,  The man I sat next to on the train ride on ChicagoI got off at the Damen station and made my way to my hostel, well scratch that, I actually first made my way to a taco joint named Flash Taco because their $4 three burrito and a coffee morning special lured me in immediately. You wave my three months in Latin America at me like that and I’ll be in your restaurant asap.

Well done, Flash Taco, well done.
I then needed to head straight to the hostel to lighten the load of my huge backpack, and by huge, I mean pretty tiny. Tiny, yet still heavy – don’t ever underestimate the weight of backpacks, especially after long walks and trekking up and down subway stairs! But for me, it’s all necessary; This thing would be carrying everything I needed for the next three months in Europe – white linen tees, my EuRail map, and my big bag of 3.4 ounce hygiene products.
The area around the Damen “El” stop seems to be where the most action is; the huge intersection is especially confusing so make sure to look both ways maybe 8 times. Not only that to keep in mind, but the general geography of the neighborhood constantly had me messed up, and I’m (typically) great at directions! No, seriously! While trying to get to my hostel, I swear I went the wrong way down Milwaukee Ave, the main drag, and then the wrong way down North Ave, the second main drag, then the wrong way down North Damen, the third main drag. I, too, was disappointed in my orientation skills, but then I arrived at my hostel, Urban Holiday Lofts, which felt 50% Urban and 50% Loft.
I booked this hostel solely because the web design was on point (and luckily the same price as the other hostels I had looked at: $28 a night), and once inside, I was convinced I had to be in the Real World Chicago house – and I love it when a brand is as well-designed as its website, so again, props to them.
I asked the front desk what I should do this time in Chicago, since I’m trying to completely avoid the downtown area, which they were in favor of. One girl at the front desk, who just got back from living in Spain and working at a surf hostel by the way, recommended I take a stroll down Milwaukee, maybe stop by the actual Wicker Park, and grab some Lou Malnati’s pizza on the way back. I swore she kept saying “illuminati” until I finally found it on Google Maps.

Milwaukee Ave

Milwaukee Ave and the streets branching off of it seemed to be where all the action is at – all loaded with cafes, independent stores, and thrift stores. Among my favorites over the two days in Wicker Park were the following:

Wormhole Coffee





If the 80s were your thing, then Wormhole Coffee will be too. The place is completely designed to be reminiscent of everything 80s, from Full House VHS tapes to Super Mario Kart on the old-school television to even a huge car (yes a literal car) parked in the back. Drinks range from the Topanga to the Koopa-Troopa, but I’m pretty basic when it comes to my coffee desires, so sorry everyone, I only ordered a small coffee with cream and sugar.

Myopic Books


Myopic Books was great, but I couldn’t take photos inside. Typical homey bookstore.

Lou Malnati’s Pizza


I always try my best not to be that person who asks for whole-wheat crust or low-fat cheese on a Chicago deep-dish pizza but this time, they asked me! The girl at the front desk of the hostel wasn’t kidding; this place is great! For $5, this personal pan low-fat, whole-wheat deep-dish pizza was delicious.

Ok so truth is, Wicker Park is more residential than anything. It’s not the Loop or the Magnificent Mile, and that’s exactly what I was looking for: the chill Chicago. I spent most of my day and a half lollygagging around the side streets, relaxing in Wicker Park (the park), and chilling in my hostel’s lounge (again, I swear it was so comfy).

Next time, Logan Square or Lincoln Park?

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