top of page
  • Writer's pictureEsther Mehesz

Exploring Chicago: A Snowy Adventure in the Windy City

Updated: Jan 28

Starbucks Reserve in Chicago
Starbucks Reserve in Chicago

Adventure day in Chicago! I was really looking forward to this day! Even the harsh weather conditions couldn't stop me from exploring the beautiful city. The snowy night before and the sleeting throughout the morning and day added an extra layer of excitement to this day. Let me take you through my 30,000-step day in the Windy City.

My first stop was to fulfill my cravings at a donut haven. I firmly believe that exploring a city requires finding the perfect sweet spot, so I indulged in not just one but two delicious donuts (I have a hard time making decisions, how can you possibly choose just one donut?!). It's all part of the experience, right? Make sure to treat yourself to some of Chicago's mouthwatering delicacies when you're there!

Stan's donuts in Chicago
You really think I can choose just one donut at Stan's?

Next on my itinerary was a visit to the iconic Cloud Gate sculpture, also known as "The Bean." Unfortunately, it was closed for construction during my visit, but that just gave me another reason that I'll return and explore it on my next trip. The city has so much to offer that one can't possibly cover it all in just a day.

Chicago bean under construction
Chicago Bean under area construction

Travel Tip

I've learned over the years from a close friend that it is ok not to be able to see and do everything all at once. If you like a place enough, you'll be back, and gives you an excuse to see it the next time around! Rather, be a slower traveler and have a coffee at a local coffee shop, or sit at the restaurant at the bar and talk with the local bartender and what they have to suggest. Embrace your location, don't rush through it.

For me, it's about the friendships and experiences that I make at a location rather than being able to check things off of a list.

Thankfully, I had the advantage of having friends who were previously residents of Chicago. They became my own personal tour guides, sending me locations of must-see places and providing valuable advice on what to do. Who better to show you around than a local, even if they can't be physically present at the time? I even got to see where they lived when they were in Chicago!

As much as I wanted to get a bird's-eye view of the city, the foggy weather made it impossible. But that didn't dampen my spirits. Sometimes, the best way to experience a place is by immersing yourself in its streets. So, I decided to explore Chicago at ground level, taking in the city's vibrant energy and architectural wonders.

Chicago downtown streets in January
Chicago in January: foggy and sleeting

One of the highlights of my day was a visit to the pier, where I embarked on an architecture boat tour. Despite the chilly weather, the tour allowed me to appreciate the city's stunning skyline surrounded by the glittering waters of Lake Michigan and learn quite a bit about Chicago's history too! It was during this tour that I even made a new friend. When you travel alone, never be afraid to ask someone to take your photo (it might not always come out the best but it's a great conversation starter). It was someone who shared my passion for discovering new places and traveling alone. We connected over a shared location too - Dubai. I have my thoughts and opinions about Dubai, and they were adamant that the next time I'm back, I'll need to make sure that they give me a local tour of Dubai. Looks like I'll need to make a trip back at some point.

Travel Tip:

Always take some form of boat tour/cruise in any place that is next to water. There's something that makes the time on the water unique and gives you a different perspective of the place that you are visiting.

Chicago architecture river cruise
Chicago architecture river cruise

To warm up after the boat tour, I sought refuge at the Starbucks Reserve. I actually hadn't experienced a Starbucks Reserve before (probably surprising to anyone who knows my Starbucks addiction back in college) as the one in Milan was overcrowded and I was curious to see what makes a Starbucks Reserve so "special". It was nice that is for sure, but way too overcrowded in my opinion. But, the cozy ambiance and hot chocolate to warm up my hands provided the perfect respite from the cold. It was time to figure out my game plan. What was next to do? If you haven't been able to tell, I'm a planner (partially). This means let me plan my flight (or in this case the car ride) and the hotel, and once I'm there I go with the flow. I have a rough idea of what I want to see and do but I'm not married to those plans. It's all about getting lost in those streets (but not too lost - safety first)! Next up...

Chicago deep-dish pizza at Lou's
Chicago deep-dish pizza at Lou's

My day in Chicago wouldn't have been complete without trying one of its most famous culinary creations – deep-dish pizza. I've had deep-dish pizza before since one of my teammates was from Chicago and we'd have deep-dish after a meet, but when in Chicago, you must eat a deep-dish pizza IN Chicago. And what better place to have some than at Lou's. I made sure to feast on this cheesy delight and savored the flavors that make it a beloved tradition in the city. It's a must-try experience that you simply can't miss.

Travel Tip

Don't be intimidated as a female solo traveler to go to a restaurant and eat alone. Honestly, chose the bar if that's an option if they're serving food. The bartenders are more than kind and there's a local right there that you get to talk to and ask what they recommend. I got to hear their travel stories, how long they've been in Chicago, and where they came from and it was a great conversation. As much as you may be traveling alone, it doesn't always feel like it.

Chicago skyline

Chicago captured my heart, and I promise, I'll be back for more. Despite the challenging weather conditions, my day of exploration was nothing short of magical.

While keeping in mind the road trip planning, the hotel once again was booked through Hilton Honors and stayed at the Hampton Inn Chicago McCormick Place which was convenient to walk from there and back into the middle of the city. It was safe (felt safe walking back to the hotel alone once it was getting later in the evening) and the amenities of the gym were great and free laundry. Took advantage of it all and would most definitely recommend it on your stay. What I ran into was that free parking was not common in Chicago, would much rather be in the heart of the city and have it be walking distance from the hotel and pay for Valet than be farther out in a random neighborhood (but that's just my opinion).

In any case, pack your bags, brave the elements, and embark on an adventure through the streets of the Windy City. You won't regret it (even alone)!

8 views0 comments


bottom of page