I fell in love with the place: The burger that ruined more than just Shake Shack
A cheeseburger, a dream, another hat, and the reality that complicated it all.
This is Part 3 of a series that ended up being a bit unexpected. What started six months ago as a short essay about a burger has turned into a story of love and loss.
If you missed the beginning, Part 1 and Part 2 are waiting for you.
It’s late October, the weekend before Halloween, and my husband and I are back in Chicago. It’s unseasonably warm, we’ve been to a handful of neighborhoods that day, and we’ve just realized how hungry we are. We find ourselves at Small Cheval for burgers.
While this is only our second time in Chicago, this visit had a very clear agenda: meet with a realtor, go see some open houses, and get a feel for Chicago real estate. We’d spent the past few months falling in love with the idea of the city, and then actually visiting and falling in love with the initial charm of the city. Now we were in Chicago again to see if we would fall in love with the reality of living in the city.
We ended up visiting close to twenty different Chicago neighborhoods during our first trip, finding our way through the city by public transit and by foot. We’d fallen in love with the city from afar at first, then visited and fell in love with it for real. While we got a great sense of the city on that trip, I was still finding it hard to look at Zillow listings and really understand what it was I was looking at.
We planned on viewing some open houses on this trip. Then, if we still liked it, we’d visit in January or February to get a real sense of Chicago winter, and to hopefully become first-time home buyers.
I already noticed a shift in how I was thinking about the city in the two-month gap between our last visit and this visit. Equipped with the knowledge that yes, I like Chicago and yes, I want to focus on a plan to move there, 2025 started looking like the year we’d leave New York behind. Our neighborhood search got more tangible, I started reading up on good elementary schools, and even had a short list of 2’s programs to start contacting in the new year, to try to secure a spot by the time we moved in the spring.
Even though nothing had happened yet, we decided this was happening. I started to plan for it and was imagining a real life there. We just needed to get through the next few months, and this trip was our way of closing the gap between our summer trip and the winter trip we were planning.
This unseasonably warm day in October that ended at Small Cheval started with seven different house tours, and everything was starting to feel even more real.
Early that morning, we met with our realtor, Quentin1 (Jordan from YouTube was down in Florida, but he put us in the very capable hands of his partner).
We spent the morning driving around Chicago’s North and West sides in Quentin’s car, viewing various homes in different neighborhoods.
He answered all of our questions and shared what he loved about Chicago. He gave us recommendations for places to eat and drink while we were here, what to continue to look at, and what open houses weren’t worth our time.
I told him we’d eaten at Lou Malnati’s the night before and that I wasn’t impressed. He confirmed it wasn’t great and told us to go to Pequod’s instead2.
Our goal on this trip wasn’t to find the condo or make the offer, but to continue to get us acclimated to the city and its real estate, beyond YouTube videos and Zillow listings. We were able to pay attention to smaller details, get a sense of what a ‘typical’ floor plan was for the type of condo we were interested in. We finally understood what it meant, in terms of apartment noise, to be one or three or five blocks away from the L.
After our morning with Quentin, I was energized. I had a similar sense of excitement and wonder that I’d felt last time, but with a grounded practicality. This was happening, and we’d just taken a huge step.
I was also starving. I glanced at a map and noticed a Small Cheval a few blocks away.
I’d read they had a good burger, and we’d passed by another one the night before that looked busy and promising (instead, we got mediocre deep dish that night — more on that later).
A little bit about me: I love a cheeseburger. It’s a meal I can almost always be in the mood for. I love a good burger and love trying new burgers, and when I’ve been running around for five hours and the weather is warm, there are few things I’d rather eat.
I had medium-to-high expectations for Small Cheval — thinking it would probably be really good but not something that I would write home about after the fact, and definitely not something that I thought would inspire3 a three-part newsletter. But here we are, six months later.
We are greeted with a simple menu with few options and place our orders. I got a cheeseburger with whatever the special sauce was, and my husband got a plain burger, maybe with tomato on it, though I can’t remember. We order fries and I pick a local beer from the menu.
We’re handed a plastic square that will light up and vibrate when our food is ready and we start to find a seat outside. On our way out, the guy pouring beer calls me over and tells me they just ran out of the beer I ordered.
I wasn’t pressed, and started perusing the menu to pick out something else. He quickly offers to give me as many tastes as I want, and also offers up a free drink.
He proceeded to go through four or five beers on the menu, offering his opinion on each one. We had some friendly back and forth, and I eventually landed on one that was similar but still local (my only two requirements at that moment).
This moment wasn’t novel. It probably could’ve happened at many of the places I frequent in New York, but things like this seem to happen a lot in Chicago. Everyone is friendlier and willing to be human with one another.
Can they tell we’re from out of town and they want to make a good impression? Or is this the ‘Midwestern charm’ I’ve heard so much about?
The people in Chicago are nice in a way that I thought I would hate but I actually find it really comforting. It’s not fake (which, unfairly perhaps, I’ve always thought Midwestern kindness to be) but rather feels quite genuine. It’s small talk, but calling it that cheapens the experience.
As a New Yorker, before visiting Chicago, I thought this would get on my nerves, and I’m as surprised as you are that I actually long for this level of kindness and interaction with strangers.
Shocking, I know.
When I got back to our table, I told my husband what happened and then remarked, “The people here really are so lovely”.
I sipped on my beer, thinking back to that moment, still thinking about how comforting that had been, and how it confirmed what I thought about the people in Chicago.
Then, the plastic square started vibrating.
I brought our burgers back to our table. When I took a bite out of the burger, I looked at my husband and remarked “holy shit”.
I savored that burger, eating it a bit more slowly than my hunger wanted me to. The patty itself perfectly seasoned, the cheese beautifully melted, and the bun they chose seemed to have been made for this moment. There were shallots and an incredible ‘special sauce’ that was sweet and tangy all at the same time.
This burger, quite literally, tasted like home, and after our morning with Quentin, that felt incredibly appropriate.
Everything continued to feel real. Over lunch, we talked about the morning — the condos we visited, the neighborhoods we liked, and the ones we thought we might be able to settle for. We compared floor plans and slowly started putting together our ‘wish list’ for when we’d come back in a few months.
I also kept talking about how in love I was with this burger.
The next day, we went to a few open houses without Quentin. Found by me on Zillow, I loaded them into my calendar and added them all to a map. I created our itinerary, starting the day in Bucktown, the furthest from where we were staying, and ending at an open house a few blocks away from our Airbnb in Lakeview.
That last condo was one we were supposed to see with Quentin, but the agent had a conflict and had forgotten he’d set up a tour with us. We almost didn’t visit this one, tired after all of the walking around we’d done, but ultimately decided to stick to our plan, given how close it was to where we were staying.
We fell in love.
We had a great chat with the realtor, who apologized profusely for not being able to show us the property yesterday and essentially ignored the rest of the open house when he found out we were Quentin’s clients.
He took us around, did a great job talking up the house. He was impressed that we were just jumping in and planning on moving to a city we didn’t have much of a connection to. He talked about how the street parking was zoned perfectly for being so close to Wrigley Field (to be honest, I still don’t know what that means, but I took his word for it).
We talked about our move, our need for good schools, and why we liked this unit so much. It was stunning and in an incredible neighborhood. The tree-lined streets were something out of a movie. We ended up staying there for an hour.
The rest of the trip was filled with more open houses, but also nice meals out, neighborhood exploration, and some light shopping. One afternoon, we popped into a Chicago-based kids’ store, Mini Wonder, and got some Chicago PJs and a hot dog sweater for our kid.
We found its sister store, Alice & Wonder, and I bought a baseball cap that said Third Coast on it. A nod to some of my previous misconceptions about my need for the ocean and to what I thought the future could hold for us.
When we got back to New York, I was even more excited about that future. I also couldn’t stop thinking about that one condo.
A few days after we got back home, the price dropped.
We told Quentin our thoughts and he went to take a look at it. He told us an offer wouldn’t hurt, if we were that interested, and so we put one in.
I wasn’t expecting our offer to be accepted, but if we were the only offer, it could’ve been a good starting point. To put it bluntly, our terms were awful — 90 days to close (because that math would allow for the smallest overlap between our lease ending and closing being finalized), and I think we offered below asking as well.
Our offer was, in fact, not accepted, and a strange wave of relief fell over me when we got the call. I shrugged at that feeling, assuming it was just confirmation that we do need to wait until we were closer to our lease ending. I put that condo out of my mind and started setting my sights on our winter trip.
As the week went on, I couldn’t help but question how strong the wave of relief was. As we talked more and more about putting the offer in, I felt more and more neutral about it — very que sera, sera; what will be, will be. It was strange to be faced with so much neutrality. Over the last, at that point, six months, I don’t think I felt neutral when thinking about Chicago at all.
I thought back to that day a few weeks before, sitting outside of Small Cheval. Six months later, I can still taste it. I am immediately brought back to sitting on that patio in Wicker Park, hearing the El train whiz by, drinking my local beer. I would keep thinking about that burger throughout the trip, but we couldn’t quite find the time to go back. We also thought we’d be back a few months later.
The week after our offer was declined, my husband was laid off, for a second time in a twelve-month period. A few weeks later, after lots of discussion and back and forth, he made the decision to go out on his own and start his own design studio.
It’s the right decision, and this is the right timing for him to do so — it’s exciting, and it’s something I think he will excel in. But it did change some of our other plans significantly.
Our move to Chicago was the first thing we had to let go of.
Back in November, we thought we’d be making offers on homes in February. We thought March and April would be spent packing, downsizing, and figuring out all the other logistics of a move across states. We thought that we’d be in our new home in May.
Instead, May arrived and we’re still in Brooklyn. We just signed our lease for another year and our kid is starting a new school in June. Other than that, it’s hard to know what the future holds, but it’s clear we’re laying firmer roots down than we have been.
Staying does feel right in this moment, and we’re reinvesting in our lives here for the foreseeable future. Since we decided to at least pursue Chicago, I feel like I haven’t thought too far into the future here. Now, I’m thinking about things like schools for my kid and gyms for me at least a year into the future — if not more. It’s a strange shift.
If I’m being honest, I was never in a rush to leave New York but I still can’t shake Chicago. Once we decided a move was what we wanted, it was what we wanted. We went after it full steam, and it’s strange not to have that dream to look forward to anymore.
There’s something there, even if I don’t know if we’ll make it to Chicago, and if so, when that will happen. We aren’t actively pursuing a move; Chicago is not off the table, but it’s not exactly on it either. We’re in this weird limbo state, but my love for Chicago has ruined the possibility of owning a home anywhere else.
When we got back from our trip in October, and especially after we realized moving this year wasn’t in the cards for us, I couldn’t even think about another burger for another two months; the memory of Small Cheval made even the thought of a Shake Shack burger completely unappealing.
As far as burgers go, Shake Shack had always been the standard and a long-time favorite. There for me when nothing else sounded appetizing, waiting at the end of a long kickboxing class, the burger I’d go to bat for when someone inevitably tries to tell me that In-n-Out is better.
Eventually, I ate a Shake Shack burger. It wasn’t the same. It wasn’t Small Cheval, and it just didn’t scratch the itch anymore. I might not have even finished it — it was so disappointing, I blocked that moment from my memory.
Small Cheval ruined Shake Shack for me in a way that Chicago gave me a dream that was snatched away.
That dream seemed to linger everywhere. The mentions of Chicago were still all around us, though I think they quieted down a bit when this shift was fresh. I felt a twinge of resentment every time I got an email from Compass about updates on my Chicago search or my kid asked to read one of his Chicago picture books.
The dream lingered in my wardrobe. I couldn’t bring myself to wear that Third Coast hat I bought on that trip. Every time I saw it, it felt like it was part of a future that didn’t belong to me anymore.
A few weeks ago, right after I published part one of this series, I put it on for the first time to run a few errands. It was the first time that I looked at it hanging in my front hallway and thought that this hat — and perhaps our dream — still feel like they belong to me.
Three parts later, and I can’t say I have clarity on what’s next. Writing about the burger was never really about the burger, but I also still don’t crave Shake Shack in the way that I used to. And when I do order it, I’m met with the same disappointment time and time again, reminded of what that burger is not.
It’s definitely not the burger from Small Cheval, but that’s not all that it’s not. It’s also the dream that we crafted of living in Chicago. From here on out, Shake Shack reminds me of that dream.
That dream lives next to the Third Coast hat — waiting to be actualized, ready when we are, if we are.
We love Quentin. If you need a realtor in Chicago reach out to Quentin!!!!
And go to Peaquod’s we did!
Yes, dear reader. This is the story that started it all. The title I chucked in my drafts folder back in November, only to continue to quietly revisit it over the last six months. When I sat down to write what I thought was an essay about a burger, I realized I had ~7,500 words that wanted to come out—thus, this series was born.
Love this 3 part series. And I so get what you are saying about being in a bit of limbo and a dream that is a bit there but not quite there right now.