Discovering Our Chicago Home: An Epic Apartment Hunt and West Loop Culinary Adventure

This past week marked an incredibly significant milestone for us, a journey that has transformed our future. While it might sound like a familiar refrain, this trip to Chicago wasn’t just another visit; it was the dedicated quest to find our new apartment and establish our permanent home in the Windy City. Arriving last Sunday morning, we strategically allocated an entire week to immerse ourselves in the apartment search, meticulously exploring various neighborhoods, and ultimately discovering the perfect place to begin our new chapter.

Embarking on this apartment hunt, I was a mix of exhilarating excitement and palpable nervousness. Despite a previous, much-loved visit to Chicago in November, this trip was different. It was only my second time in the city, but this time, the stakes were real. There was no room for speculation, no lingering uncertainty, no “maybe if we move to Chicago…” thoughts. The move was officially happening. The pressure was undeniably on, and I confess, I harbored a slight worry that the magic of the city wouldn’t resonate as strongly the second time around, especially with such a monumental task ahead.

Weeks before our trip, shortly after our wedding, we initiated preliminary research. This involved connecting with a diverse group of people: apartment brokers who graciously offered their services free of charge, friends of friends residing in Chicago who provided invaluable insights, and a general online browse of available listings. However, we understood that the bulk of our decision-making would unfold during our dedicated week in the city, allowing us to experience the neighborhoods firsthand and assess properties in person.

Our comprehensive trip was a delightful balance, split almost perfectly between intense apartment hunting and indulgent culinary exploration. While the apartment search undeniably became a bit exhausting at times, the incredible array of food experiences we encountered more than compensated for the weariness. For those eager to follow our gastronomic footsteps, I’ve compiled a detailed list at the end of this post, highlighting all the fantastic places we savored during our time in Chicago!

Given that Connor and I had limited familiarity with most of Chicago’s distinct neighborhoods, beyond a vague sense of areas we might prefer, we opted for an innovative strategy. We booked three different Airbnbs, strategically located in three diverse neighborhoods: Lincoln Park, River North, and West Loop. This brilliant idea, conceived before our wedding, proved to be an absolute game-changer and comes highly recommended for anyone relocating to an unfamiliar city. This approach allowed us to truly immerse ourselves in each area, interact with local residents, and experience a genuine “home-like” feel that traditional hotels simply cannot replicate. More importantly, it afforded us the invaluable opportunity to explore and walk around these neighborhoods as if we were already living there, gaining a much deeper understanding of their unique character and daily rhythm.

We landed in Chicago mid-Sunday, choosing to postpone the official apartment search until Monday morning. Our initial Airbnb was nestled in the vibrant River North neighborhood, placing us right in the energetic heart of the city. This area immediately impressed us with its proximity to countless shops, an abundance of diverse restaurants, and, to my particular delight, the magnificent Eataly.

In fact, Eataly was our very first destination upon arriving in the city. Having visited the New York City location several times, this was my inaugural experience at the Chicago branch. We indulged in a superb platter of charcuterie and cheese, accompanied by a simple yet perfectly crafted salad, and raised a toast to our impending apartment hunt with their exquisite house-brewed Saison beer—a truly delightful start. While Chicago boasts a million amazing food destinations, the prospect of living within arm’s reach of this mecca of Italian cuisine and impeccable ingredients instantly ignited my excitement. The trip was undeniably off to a fantastic start!

Bright and early the next morning, the serious apartment search commenced. We began by viewing a few direct-by-owner listings before transitioning to a whirlwind tour of numerous apartment buildings scattered across the expansive city. For those familiar with Chicago’s geography, our search spanned a considerable area, stretching from Lincoln Park – the furthest north we considered to optimize Connor’s commute time – all the way down to the South Loop. This broad approach allowed us to explore a wide range of options, understand what our budget could afford in different districts, and thoroughly evaluate various neighborhoods for their unique offerings and ambiance.

Monday, Tuesday, and Wednesday were almost entirely dedicated to viewing apartments, either in person or frantically searching for last-minute online listings. We quickly discovered a critical reality of the Chicago rental market: desirable apartments disappear at an astonishing speed, often within mere hours, especially during this peak season. Multiple advisors strongly urged us that if we found a place we truly liked, we should submit an application immediately and make a decision swiftly. It was a stark choice: commit to a place right away or risk losing it entirely. Talk about pressure!

By the end of this intensive period, we had worked with four different brokers and toured well over 20 apartments in total. Some were variations within the same building, showcasing different floors or floorplan configurations, but the majority were in distinct buildings across various locations. We encountered an incredible spectrum of living spaces, from a cozy unit within a two-story townhouse to a breathtaking apartment on the 57th floor of a towering building. We saw modern designs, traditional layouts, incredibly dark spaces, and brilliantly well-lit ones – you name it, we probably saw it. We even viewed one apartment situated directly above the ‘L’ track, which, as you can imagine, was unbelievably loud and an immediate disqualifier. I’m quite certain our cat, Max, would have spent the rest of his life cowering under the bed. The entire process was a whirlwind, requiring us to capture countless photos on our phones just to keep track of all the properties we had seen!

After thoroughly exploring numerous options and gaining a much clearer understanding of our preferences, we seemingly found a promising apartment in River North on Tuesday evening. We proceeded as far as filling out an application to reserve the unit, eagerly sharing the good news with our families that very night. It appeared our arduous hunt had finally concluded.

While Connor and I felt relatively good about our choice, a nagging thought persisted. We couldn’t shake the feeling that we should perhaps view a few more places the following day, just to be absolutely certain. This internal debate was fueled by the fact that we had already scheduled an appointment with another broker to explore additional neighborhoods the next morning, an opportunity we felt was too important to miss.

The next morning, with a refreshed sense of purpose, we woke up bright and early to journey to one of the neighborhoods we had heard so much about – an area consistently recommended to us, but one we hadn’t yet had the chance to truly explore: the West Loop. I had been in touch with this particular broker for several weeks leading up to our trip, and I had a strong intuition that she possessed an excellent understanding of our preferences and what we were seeking in a new home.

Our initial viewing in the West Loop was a smaller, decent unit within a building, but we quickly ruled it out. The reason? A high-rise was actively under construction directly in front of its windows, which would inevitably block nearly all the natural light, a crucial element for us. No, thank you.

Following that, we headed to what would be our final option in the West Loop. At this point, we still hadn’t had much opportunity to walk around the neighborhood or truly get a feel for the surrounding area. However, we were instantly captivated by the next unit. It was noticeably larger than the apartment we had considered in River North, and the light was absolutely incredible – a coveted southeast exposure! Furthermore, it was significantly more reasonably priced, the building boasted fantastic amenities, it featured a standard-size gas stove (a welcome upgrade from the electric stove and apartment-sized oven in the River North unit), and to top it all off, it was within easy walking distance of both Whole Foods and Mariano’s. The combination of these factors made it undeniably a much better option for us.

At that precise moment, we quickly and decisively concluded that this West Loop apartment was the superior choice, regardless of our as-yet-limited impression of the neighborhood. We immediately filled out an application, feeling a profound sense of relief and excitement. To help us truly familiarize ourselves with the surrounding area, our broker then led us on an impromptu walking tour. Within just a few minutes of starting our tour, both Connor and I were bubbling with incredible excitement. Greektown, with its charming family-owned restaurants and small Greek grocers, was literally steps away. Our apartment was also a mere 5 to 10-minute walk from Chicago’s infamous ‘Restaurant Row’ – an area absolutely teeming with amazing eateries, historic old-school butcheries (a nod to the area’s past as a meat-packing district), and various restaurant supply stores.

It was around 2 o’clock in the afternoon, and the area was alive with people dining al fresco, enjoying lunch. The entire district felt incredibly vibrant, yet it retained a distinct neighborhood charm and was noticeably quieter than River North, a quality we both greatly preferred. We discovered hidden gems at every turn. Within a block of ‘Restaurant Row,’ we stumbled upon a tiny alley transformed into an outdoor Texan BBQ joint called Green Street Smoked Meats. This same alley housed a tucked-away ramen spot and a secluded champagne bar. Across the street from this vibrant hub was Chicago’s magnificent SOHO House, housed within a beautifully repurposed old industrial warehouse. Its first two floors are open to the public, featuring amazing little cafes, including a chicken shop, a pizza place, and on the ground floor, The Allis – a beautifully appointed lounge and cocktail bar, perfect for bringing a laptop, reading a book, or getting some work done.

All of this, just arm’s length from our potential apartment? We were completely sold. To make a long story short (though this post is quickly approaching epic proportions!), we officially chose the West Loop apartment and are eagerly preparing to move in on June 10th. This timing allows us to settle in comfortably before Connor commences his residency a few days later, ensuring a smooth and stress-free transition into our new life.

Neither of us anticipated feeling such profound confidence in our new neighborhood or this level of sheer excitement for the upcoming move. The surrounding West Loop area is incredibly vibrant, and I know its dynamic food scene will be an endless source of inspiration for me, both personally and professionally for my work. Not to mention, it’s simply such a fun and engaging area to live in.

I am also particularly eager to start cooking in our new kitchen. With direct sunlight pouring in, I’ll be able to capture many more process shots for the blog, enhancing the visual storytelling of my recipes. Perhaps this new setup will even encourage me to venture into experimenting with cooking videos! Moreover, I’ll finally have a dedicated and much-needed space to focus and do work – essentially, a real office, which has been a long-awaited luxury.

Naturally, we are still sad to bid farewell to our cherished family and friends in the DC area; if we could bring them with us, we absolutely would! However, I have a strong and optimistic feeling that we will absolutely adore Chicago. Here’s to many exciting adventures, and an abundance of truly awesome food experiences awaiting us in our new home!

Our Chicago Culinary & Exploration Highlights: A Must-Try List

Here’s a curated selection of places we visited during our trip – we genuinely didn’t experience a single bad meal!

West Loop Gems

Little Goat Diner
Located directly across the street from Stephanie Izard’s acclaimed The Girl and the Goat, this diner is a breakfast, dinner, and everything-in-between institution. Its menu is incredibly creative and packed with amazing options. We particularly loved the ‘Little Piggy Went to China’ breakfast dish, featuring a cheddar-scallion biscuit, perfectly cooked sunny-side eggs, Szechuan pork sausage, chili garlic chive sauce, and fresh blackberries! I can already envision this becoming our favorite weekend breakfast spot.
Parlor Pizza Bar
A fun, casual everyday pizza joint boasting an impressive beer selection and ample outdoor seating. We celebrated finding our apartment here with the ‘Burrata Be Kidding Me’ pizza – a delightful white pizza topped with arugula tossed in a lemon-truffle oil vinaigrette!
Soho House
While we haven’t had a full meal here yet, I’m already utterly obsessed. My fascination stems from its stunning interior design, the expansive space, and the beautiful food displays in The Allis, not to mention the appealing prospect of bringing my laptop and getting some work done in such an inspiring environment. Plus, I’ve heard rave reviews about their avocado toast topped with poached eggs. This place could easily become my happy (and perhaps expensive) place.
Vivo
A beautiful Italian restaurant nestled right in the heart of Restaurant Row. Vivo impressed us with its excellent homemade pasta dishes and simple, yet elegantly prepared Italian cuisine. It’s known as one of the area’s oldest and most respected dining establishments.

Lincoln Park Delights

Kameya
Our Lincoln Park Airbnb hosts recommended this tiny, hidden 10-seat sushi restaurant, and it turned out to be some of the best sushi I’ve ever had! The fish was exceptionally fresh, and their yellowtail ponzu starter was delicious. The creative rolls were a highlight, and I’m already dreaming of a return visit.
Butcher & the Burger
A casual yet incredibly creative burger joint offering everything from pork, bison, salmon, and grass-fed beef to vegetarian options, with tons of different customizations. You choose your patty, spice seasoning, bun, toppings, and all the extras! Their hand-cut fries are among the best I’ve ever tasted. As an added bonus, they even offer pig butchering classes!
Annette’s Italian Ice
A quintessential walk-up-to-counter ice cream, frozen custard, and Italian ice shop, charmingly situated on the side of an old brick building. They offer classic flavors alongside local favorites like the Chicago Pothole (chocolate ice cream with chocolate fudge swirls and chocolate chunks).
Strings Ramen
With locations in Lincoln Park and Chinatown, Strings Ramen serves truly excellent ramen with all noodles handmade in-house. We particularly enjoyed the Tonkotsu Ramen, crafted with a rich 48-hour slow-boiled Berkshire pork bone broth and topped with incredibly tender pork belly, crushed garlic, nori, scallions, and a medley of other delicious ingredients. It’s a rich and deeply satisfying bowl.

Gold Coast & River North Flavors

Velvet Taco
A new, casual taco joint in the Gold Coast (originally from Texas) that serves some of the most delicious and creative tacos I’ve ever tasted. Their Ahi Tuna Poke lettuce wrap taco is particularly amazing; I could easily eat ten in one sitting! Any place that hand-presses their corn tortillas with each order is a winner in my book.
Gilt Bar
A fun and surprisingly reasonably priced restaurant in River North, known for its superb craft cocktails (their Pimm’s Cup with ginger beer was fantastic!) and inviting ambiance. Connor enjoyed a delicious gnocchi with pork belly, while I savored a charred octopus main course with garbanzo beans.
Eataly
Somehow, we managed to visit Eataly at least three times during our Chicago trip. Need I say more? I could literally spend hours exploring their cheese department alone; it’s a true paradise for food lovers.
Osteria la Madia
An unpretentious Italian restaurant in River North serving excellent pizzas. It’s easy to get a table on a weekday and embodies the kind of reliable spot you can imagine returning to time and time again for a satisfying meal.

Must-Visit Attraction

Lincoln Park Zoo // LINCOLN PARK
This zoo has quickly climbed to the top of my list of favorite zoos ever! It’s entirely free and open to the public, just steps away from Lake Michigan, and boasts some of the best animal exhibits I’ve seen, featuring truly unique animals. Plus, they currently have an incredibly adorable 2-month-old baby gorilla! It’s a ridiculously charming experience.