Visiting the Windy City during the frigid month of January may not sound appealing at first, only to moments later turn it exactly into what you needed.

Cold, yes! On the other side, no lines, no overpriced hotels and flights, no crowds and somehow no noisy. The city was considerably empty. Wondering around, the only sound we would constantly hear was the train passing above our heads. All that calmness made it all worth it despite the unwelcoming weather. In fact, the weather was the least of our worries during our trip to Chicago.

My sister was in town from Brazil, what pushed us to make the trip regardless the cold before she would go back. In fact, let me say that she was the most excited for Chicago, especially because of the low temperatures we were going to face. Clearly, being from Brazil has no influence on her weather preferences. The reasons why choosing Chicago among many other warmer destinations were my sister’s desire for cold and a couple of good reviews from friends. Oh, I almost forgot, food also had a vote.

The dark clouds above the grayish landscape seemed a perfect match. The brave ones who would dare to leave the coziness from home seemed to follow the trend, wearing the same palette of colors than their surroundings. Walking around, the only sparkly sign would be the flashy lights from The Chicago Theater or my sister’s fluffy pink coat. I believe she was one of the few really embracing those conditions.



I am not going to lie, I am a pizza lover, so you already know what I was after. Although reading that the famous deep-dish pizza has been overrated, I still was determined to have it. We picked one out of the many places that offer it based on location and some decent Google reviews. We opted for Gino’s East South Loop. Cozy, small, calm. There was no reason not to like it and the food certainly did not disappoint. We ordered the famous Chicago deep-dish style pizza, loaded with meats, mushrooms and cheese and paired with a delightful caprese salad and a local draft beer. Feeling a little bloated, however happy and satisfied, we walked back towards our hotel once there was nothing else we wanted to do more than lay out and call it a day.


Our food experience around the city included pastries and cupcakes, from two adorable places called Goddess and the Baker and Molly’s Cupcakes, and of course lots of coffee. A complete brunch from Wildberry Pancakes and some bar food from Miller’s Pub were also part of the trip.

I would say the peak of visiting big cities on low season might be the photographs. As first-time visitors in Chicago, we wanted to take as many great memorable pictures as possible and we sure did. As I mentioned before, there were no crowds of people around. That meant no strangers standing between you and the monuments. That meant no photobombs. That meant pictures at The Millennium Park where you can easily spot The Bean standing majestically behind you. Unfortunately, the weather didn’t allow us the experience the view from the top of the Skydeck, where all we could see in front of us was a thick white sheet. At least we got a panoramic view on board of the Navy Pier Ferris Wheel to compensate.

Overall, Chicago felt very practical, from the moment we arrived and took the Blue Line all the way to downtown until the moment we left. We stayed by The Millennium Park, what was indeed very convenient. All the attractions were reachable by foot, from the Riverwalk to the Pier. However, let me mention that we both are walkers. Walking 30 minutes may sound a lot to you but it isn’t for us. As a bonus, we save money on transportation and get to see more of the city.

Our three days in Chicago were filled with walking, food, coffee and photographs. On our last day we got lucky enough to see the snow. Not that I was super excited for it, however it was my sister’s first snow, what made it even more special. I guess it doesn’t matter what time of the year you go to Chicago, it will always have something to offer you.

The bonus of going on off-season was that we got to see more of the city as it is. Mostly locals rushing around, going to work and having a drink after. You don’t hear your native language everywhere you go, in fact, I don’t record hearing Portuguese at all. Chicago during the summer, I assume, is packed, more vibrant, louder. In the winter, it doesn’t mean the city is any less interesting, although it feels serious, more reserved. Those characteristics, matching my own personality, meant that there was no better time for myself to meet and greet the Windy City.

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