50: Chicago, The Relationship That Was Good For Me

Had you asked me two years years ago, or even three years ago where you’d think I’d be, here wouldn’t have been in my top ten. Flying into Chicago, after moving into my LA house is such a surreal feeling. Surreal in the sense that I never expected to miss Chicago. When I first found out I’d be moving from Los Angeles to Chicago, I cried. And not just a few tears, I ugly cried for longer than I care to admit. I’d always loved the city, and even wanted to go to college there when I was in high school. Deciding to stay at college in my hometown meant that I made more than a few trips to the city, pretending that I lived there, getting into bars underaged and calling the train the “L”.

Lesson 91: Most people who live there don’t call it the “L”. Technically it stands for the Loop (all the trains loop around downtown) but that’s not the only place they are so it’s a little silly to call it the “L” when you’re taking it to the south side or far north.


Either way, Chicago was a place I would’ve moved after Ohio but once getting out of the Midwest in 2013, I had no plan of returning. Until now.


So I cried. I listened to people get excited to get there first choice while I was stuck with my third. Los Angeles was at the top of the list with New York City in second, but if I didn’t accept Chicago as my new base for work, I’d have to quit after all the hard work and six month hiring process. So, I decided to suck it up. I began to get excited about the fact that I didn’t get New York with everyone complaining about living in shoe boxes and called my then distant best friend Douandy who lived there and begged him to help me.

Fun Fact: I hadn’t seen Douandy in over two years, and talked to him via Facebook a few times a year. We were best friends in college but once we moved our separate ways, became distant. Luckily, this didn’t matter.


After training, many people don’t know this but the airline company only gives you three days off to move. Three days to fly back and forth to wherever you lived before doting a plethora bags. Three days without training to look for an apartment. Three days to learn your city and your airport. Three days until you start flying all around the world with no supervision. Three days to get your shit together. Fuck!

Fun fact: I curse way more as a flight attendant than I ever have my entire life.

Luckily for me, I had Douandy. Not only was someone he worked with looking for a roommate, but it was in my price range and available immediately. Her name is Maya and, if you remember correctly, we went to places 29 and 30 together. Needless to say, it worked out beautifully however at the time, I had no idea.


As soon as we landed in Chicago, I went to my hotel to wait for Douandy to pick up both me and Andie so I could check out my soon to be two year apartment. Maya was as nice as Douandy had described and when she asked when I could move in I responded with “As soon as I can get a key”. We laughed for about an hour decided to all go get food at Andie’s brother’s restaurant in Logan Square and it was that moment that I knew Chicago would be quite alright. I was sitting in my new temporary home with a friend I hadn’t seen in years, a girl a met in training two months prior, and a chick I decided to move in with after knowing her for two hours. They’ve all been in numerous blogs and became the stability I never thought I needed. But that’s later.


My first six months in Chicago I wasn’t active in the city. Constantly complaining about being California sick, I began flying back to the sunny state every few weeks in between traveling for this blog and for work. I barely hung out with Maya because half the time I was God knows where, coming in and out with loads of luggage as she studied for her final year of college. We’d occasionally make dinner and watch a movie but we weren’t by any means “best friends” during that summer.


At the beginning of the summer is when I decided to start my blog. While sitting on a barstool at Douandy’s job wondering how the hell I got here and looking for a creative outlet, I got an idea. Through suggestions from more than a few people, I landed on ‘50 places in 50 weeks’ and told him to run the receipt paper through so I can make my list. This was my list. I lost the paper long ago but thank god for social media.


I decided to start this blog and went one of the first places, New Orleans. I got to choose a companion for a year so that first year it was Douandy. He lived near by, had the money and flexible job to travel, and we got along. It was perfect. But the more we travelled, the more I realized I didn’t know much about the city that I lived in. I’d been to London twice but I’d never seen a 20$ Second City show. Inexplicably, once winter started to settle in, I decided not to travel to places that weren’t on that list. This meant no unnecessary travel. Either it’s for work or it’s for my blog. I needed to give myself time to enjoy my own city.

That October, started it for me. Me, Maya, Douandy and Maya’s boyfriend Jake carved pumpkins, watched horror movies, and got 3$ burgers from around the corner. It was great and for once, I began to feel comfortable.


That next month I realized I was never going to sustain my travels if I didn’t start working a little more so I started working at (drumroll please) Douandy and Maya’s restaurant, Bogart’s. I served. I sucked at it but there I made friends. Lasting friends that didn’t leave the city every other day, Audrey being the closest of everyone. From there I started going out more and before I knew it, Chicago was my city.


I loved getting off a double work shift at midnight only to dance until five in the morning and wake up at eleven for brunch. I loved being bored on a Wednesday and catching the bus to an arcade bar and a trivia night across town in the middle of a blizzard because I didn’t feel like driving. I loved how I thought tights, a skirt, and boots was warm enough to cover my legs in the middle of February while it was 12° outside. I loved how the city opened my eyes to things I once thought I was too good for by knocking me down a few pegs, having to scrape the bottom of my purse for a train fare only to catch it in the wrong direction. (That only happened once!) I loved it. But more importantly, I loved the people.

That next year I met three amazing souls completely by chance. Given, I’ve met plenty of people whom I loved in that city, but these were different. I didn’t meet them because we worked together, or some event. I met them by chance. I met them because we so happened to be at the same place at the same time and thought “we should hangout because I like you as a person”. Sarah came to California with me, Nora to Barcelona for my birthday and drove with me to California when I had to move, and Megan, whom I met while serving me a mimosa, I see regularly when I go back to Chicago and I’m trying to drag on an adventure. These are the kinds of people you meet in Chicago and when you too, have a good soul. There are many favorite things I have about this city and I could talk for hours but I’ll try my hardest to stick to the highlights, alright?


Oh my god, the food. The food is seriously some of the best in the states and I’m not saying that with a bias opinion. It’s true. Okay maybe I’m slightly bias. Whatever. It’s bomb. What’s funny is as much as everyone talks about Chicago deep dish pizza, that’s just one of the things they specialize in. Now I could easily give you a review of every single restaurant and what they look like but I’m not culinary artist. I’m not a food critic, I just like to eat. Instead I’m going to tell you which restaurants to go to and why. That’s it. Easy right?

The Chicago Diner: Hands down best Rueben I’ve ever had and the milk shakes are to die. Not to mention, it’s vegan. And this is coming from someone who enjoys meat very much.

Lou Malnati’s: Everyone goes to Chicago and says “I want deep dish pizza” and then they go to Giordano’s. No. I mean it’s good but if you want bomb ass deep dish, go here. It’s better

Revolution: Bacon Fat Popcorn. Melt in your mouth burgers. More than thirty beers on tap brewed in house. Yes.

Kuma’s: This heavy metal burger joint where the burgers are named after bands and you can’t substitute anything. Not to mention all the servers have a mad amount of tattoos.

Red Door: Their fried chicken breakfast biscuit is something to be cherished. Then there’s bottomless mimosas.


Portillo’s: Just go and thank me later.

Wildberry: Their lattes are crack and their cinnamon roll pancakes taste like freedom.

Stan’s Donuts: I don’t even frequent donuts and I’d trip a child for the last Stan’s of the year.

Lula Café: They have an olive oil, cinnamon, parmesan hollow noodle dish that sounds weird but will make your soul do a happy dance.

Hops and Barley: 3$ burgers and 4$ well drinks every Monday. Yes.

Golden Nugget: If you’re hungry after the bars are closed, go here.

John Hancock’s Signature Lounge: Go for the view if nothing else, grab a drink and enjoy the regalness of it all.

The Bars.
Yes, I have to make this its own category because the bars here belong in their own category. There’s Wicker Park, River North, Lincoln Park, Bucktown, Boystown, Wrigleyville, and my favorite Logan Square. Obviously there are far more places than these but these are the areas I ventured to the most.

Wicker Park

It’s the neighborhood I took every friend to that came to visit and possibly the entire reason why I wanted to move to Chicago in the first place. A heart broken Josh Hartnett starred in the movie Wicker Park with Diane Kruger and Rose Byrne, and spoke to my dramatic 13-year-old self. The vibe of the movie made me truly believe that both Wicker Park and Josh Hartnett were the ones for me. Fast forward ten years into the future and here I am, trolling the streets at three in the morning and waiting in a ridiculously long line for late night Flash Tacos right by the Damon train stop. It’s chill, trendy vibe, phenomenal food, good local shopping boutiques and eclectic bars are just a few reasons why I loved to show it off. A couple gay bars, a bunch of dive bars, some clubby spots, live bands, karaoke, a barcade, a rooftop, you name it. Now it isn’t this big downtown type place you’re expecting its more than a little close and quaint. The buildings aren’t more than a few stories high and they all sit on top of each other as the train runs through them above ground.


Fabitat is one of my favorite spots as it is only open two Wednesdays a month. It hosts themed drag shows and plays in the underground back part of a lively bar on weekends called Double Door. What’s funny is that Double Door is nearly the exact opposite of Fabitat. Also in Wicker is Nicks Beer Garden, which has karaoke night on Sundays and three dollar beers, but more importantly is predominantly men so I can almost always chill and get free drinks. Win win. Lastly there’s Debonair, or as we nicknamed is Da Boner. Don’t ask, we do what we want. It has a burlesque show on Wednesdays with two dollar PBRs and then Thursday’s is this 80s/90s mix that included trippy David Bowie music. There were two floors, one being the basement which has its DJ enclosed in a glass booth and red dim lights everywhere. Upstairs had mannequins and old fashioned chairs and couches in the windows. If you went there enough the staff didn’t mind if you sat in them, people watching the passersby.

This is where, you’ve guessed it, Wrigleyfield is and the bars are themed as such. The easiest way to describe my love hate relationship with this place is just imagine all the frat boys you ever knew graduated, and then moved to Wrigleyville. It’s fun, fast paced scene is exactly that while the people who roam the area are usually intoxicated. Wrigleyville is the place you go if you plan on pregaming hard and having a headache in the morning, but it can be a damn good time.


It’s close to but not to be confused with Lincoln Park, the city not the band, and hosts two of my absolutely favorite bars, Kingston Mines and AliveOne. Kingston Mines, or just Kingston’s is hands down my favorite in the city. It’s a five am jazz/blues bar that has two separate stages, chill vibes, and bomb ass barbecue. There is a cover to get in but when I say it’s worth it, I mean it.


The drink prices are reasonable and no matter the day of the week it’s a great spot to go, chill, and get funky. That and it’s within a ten minute walk from AliveOne. AliveOne usually doesn’t host live bands but has a front area with a billiard table and high top bar tables. Tthe backroom has a DJ booth, a stage with couches, and an iridescent disco ball hovering over an intimate dance floor. Tuesday’s is funk night where you can get groovy to 70’s music while enjoying their selection of over forty beers on tap for only $2-3. I can dig it.

Logan Square.

Logan is where I usually feel the most at home not because it was closest to my apartment but no matter the day of the week, the bar I went to, I always had a good time. I didn’t have to think about what to wear or wonder what kind of night I would have because it was consistent. Wednesday’s were the usual as it started with a drink at Heavy Feather which was this classy upstairs, party downstairs kind of grundge. Then it was usually followed by cheap beers and free comedy across the street at Coles which houses guests like Hannibal Buress. Then over to Emporium which was this graffitied warehouse barcade that housed a taco food truck and during Halloween season had a haunted house.


Lastly there was The Owl which was this funky 70’s vibe of a bar with a cigarette vending machine and local DJs that played til 5am. Yes and yes.

Given that I spent over two years learning as much as I could about Chicago as a 23-25 year old, I could very easily write an entire book strictly on the bar scene alone. However, knowing that my audience isn’t full of Frank and Lip Gallagher’s, there are many more aspects to the city than just the bar scene. Anyone that asks how I like/d Chicago, I always say the same opening sentence: “It’s the best city in the United States three months out of the year.” This means, if you visit during the summer, there is not a chance in hell you’ll have a bad time, unless of course you’re the worst person in the universe but I save that title for special souls like Hitler, and party. During the summer it’s this vibrant, lively, warm, big city, beach town and has an event going on nearly every day, let alone every weekend. Don’t believe me? Here’s a bullet point list.

1. There is a street fest nearly every weekend

2. The street festivals are littered with local brewery tents, bands, and crafts to purchase which are usually hand made and original
3. Myopic Books is my favorite bookstore I’ve encountered in The States with three and a half split levels of old and new books. Not to mention it’s DIY built vibe is the best part.

4. The beach, though it’s on a lake, is beautiful with bike trails and sits on the edge of downtown
5. The dog beach is fuggin adorable and can feed anyone’s puppy fever
6. It hosts popular festivals such as Riot Fest (mostly alternative), Lollapalooza (mixed bag/main stream artists), North Coast (mostly EDM), Grateful Dead (literally three days of them) and many more smaller shows

7. The weather is warm, not only warm but hot! 100+ sometimes
8. Everyone emerges from hibernation to do outdoor activities all day, every day.
9. The zoo is huge and fun and free
10. Millennium Park hosts a weekly movie night on a big projector downtown that’s byob and you can pack extensive picnics

11. It’s way easier to take public transit because the tracks aren’t frozen and you don’t mind walking to the bus or train stop
12. Concerts galore!

13. All the super attractive people wear 1/4th clothing witch is a plus
14. Baseball season starts so you can go to the million games they have and hangout in Wrigleyville which is hella fun
15. You can finally start renting the street bikes for cheap (Divvy’s) because it’s not freezing
16. It’s usually when your friends choose to visit and gives you an excuse to do all this stuff

17. The pride parade is one of the largest in the country and it’s a ridiculous amount of fun

18. Um, can you say boat season?!

There are obviously plenty more reasons than this but these are the main points on why having to leave Chicago right before the summer broke my heart. Everyone comes out of their shell, the streets are littered most hours of the day from late night bar goers to early morning rooftop yoga sessions. I’m sure there are things people could find wrong with Chicago, even during the summer, but like I said, they’re probably some of the most miserable humans in the worlds and think puppies are annoying and rainbows are ugly.

One of my favorite things about this city, and why I adjusted so well to moving against my will, is most likely based on the people. Like I said in the beginning, I was slightly spoiled because my best friend had been living there for two and a half years, which allowed me to latch on to his group of friends. That, and I always had a companion to troll with. However, eventually I began to make friends of my own simply because it was just so easy.


Everyone here has the fast paced, city vibe with the underlining mentality of your average, friendly midwesterner. Making friends with your bartender wasn’t typically just because they were being polite, it’s because they authentically liked you as a person and when you exchanged numbers, you’d hear back from them. Meeting people at bars wasn’t weird, sketchy, or desperate (unless of course they tried to sell you drugs), it was the norm. I could walk outside of a restaurant, ask someone to borrow a lighter, and next thing you know they’re on my couch a week later for a wine night. Normal.


I never really talk about work, simply because I don’t like to put to much emphasis on my job, but considering I lived in Chicago while getting acclimated to flying non-stop, it’s only fitting that I do.


Flight Attending, as a job, is hella easy. The training is a tough two months in a remote location in the middle of nowhere in Fort Worth, Texas where you go to class 9-12 hours a day, six days a week. We had tests at least three times a week in which we had to get a 95% or higher on and if we failed one, we were sent home. Even if it was the last test, you were sent home. Then afterwards we took a plane directly from graduation to base and given three days to cope and once we were on the plane, guess what we did? Served cokes, cleaned up puke, and stood by in case the plane started to go down. Now I’m not trying to downplay the job, but on any given day, that’s what I do. Therefore, as a whole it’s easy. The lifestyle however, is hard.


Social media plays a large part in this as once you, or at least I, started traveling everywhere, it was so exciting that I posted non-stop. I would post when I got called out to go to London with four hour notice, or anytime I had a downtown NYC layover with a view of the Empire State Building. I’d post when I rode horses on a beach in Mexico and went shopping in Milan a week later. I posted everything. And when I began this blog I posted some more. What people didn’t realize however is that, almost all the time I was alone. I’ve been single my entire life and was raised an only child so being alone was normal. I’m not telling you that to feel bad, it’s just the truth and on most days I was okay with it. But when your traveling the world, and seeing these amazing places, being alone becomes just that; lonely.


I learned more about myself the two years I spent in Chicago than I’d figured out my entire life. I had mental breakdowns when I’d beg friends to come visit only for them to bail or complain they were too busy. I’d cry on layovers when I was forced to go to fucking Orlando for the thirteenth time instead of being home for my friends bridal shower. I’d watch my phone like a hawk waiting for someone, anyone really, to ask me how I was doing only to land to a voicemail from my student loan company. Some days, it was unbearable.

I spent so much time in my room those first few months of living in Chicago simply because I had no where else to go and no one else to talk to. I’d try to date but they’d think that because I was a flight attendant who was “gone all the time” that clearly I was only looking for casual when that wasn’t the case. I had mad anxiety followed by towering depression that I had to get in check all the while I was posting these extravagant pictures of my all inclusive Los Cabo’s layover when in reality I haven’t seen a single one of those flight attendants since that trip. The job is lonely, and you hardly fly with the same people more than once in a six month period so your friendships can be very hard and distant. Chicago helped me out of this.


The friendships I made were mostly with people not in the aviation industry so that when I came home, I didn’t have to worry about who was traveling where; they were always in the city. Our city. Chicago helped me through the hardest time of my life helping me battle my depression/anxiety nightmare with opens ears and arms of the beautiful souls I had around me. People that knew my schedule would make sure to have days off that I’d be in town just so we could see a movie. People who became practically roommates for two days because they’d know I was stressed and needed the company. People who I had friendsgiving and gift exchanges with. People who became apart of my constant, crazy, fun, and mildly toxic life not because I offered something to them but simply because they appreciated me as a person.


When you get to a certain age, particularly your mid twenties, you’re in this weird limbo where you’re obviously a fully functioning adult but you still have your childish, destructive habits. This was us. We roamed Chicago as driven, 20 somethings without a care in the world with an appetite for adventure. When I think of my first flight in versus my last flight out, it’s almost bizarre. On both of those flights I cried, but for completely opposite reasons. When I left Chicago, I’d no longer be able to come home to a house full of people ready to troll the city. I’d no longer be able to order Chicago Diner takeout every other week just for the vegan milkshakes. I wouldn’t be able to spend lazy mornings having mini jam sessons.

Processed with Snapseed.
Processed with Snapseed.

But instead of focusing on the wouldn’ts, I started to focus on what I had. When I came to Chicago I expected to stay maybe a year tops, not more than two. I expected to make a couple friends, not dozens. I expected to grow as a person, not completely change my outlook on life. Chicago reached far passed any and all of my expectations. It became my rock, my love, my heart and my city. I could complain about the weather but, come on, I could complain about the weather on any given day in any given city. I wished I wanted to stay there, I wish I was satisfied enough to make it my home but it simply is not that. Who knows, maybe in five years I’ll move back or maybe I’ll never live there again. There’s no way of knowing and honestly, I don’t mind.


It’s the perfect love, my best friend, and a vivid memory. It helped me be the person I always knew I could but simply isn’t my forever. Chicago is the unexpected relationship that was good for me, and damn, was it fun.

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