Exploring Chicago in Winter - Gishitravels

Exploring Chicago in Winter

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The ‘really’ Windy City!


Solo Trip to Chicago, Illinois

I flew in to Chicago, Illinois one January to take care of some business at the Consulate. From the O’Hare Airport I hopped on the shuttle that would take me to the hotel where I would be staying at for a couple of days.

Chicago AriportChicago Ariport

The view outside of the hotel where snow was still on the grounds. 

chicago hotel

The consulate process did not take long because I have already prepared the necessary documents, after all, it would not be wise and easy to fly back or roam around the city for one necessary paper.

solo trip

It was on this trip that I discovered my solo travel spirit! (I think it’s fierce :-)) We heard a lot of negative things referring to Chicago these days, especially about safety, but there were still some nice stuff in the Windy City, just like anywhere else, if we would just be cautious and use common sense.

Chicago trains

I had been on a 24+hour flights from the US to Asia transpacific and transatlantic by myself, but by solo traveling I mean the one where you explore an unfamiliar place by yourself at the same time satisfying your curious wanderlust.

Chicago trains

Shivering in the middle of winter, I wanted to experience what a ‘tourist’ should see. I hopped on the train, got on the bus, walked blocks upon city blocks, using only my then iPod Touch catching and accessing café and other businesses’ free wi-fi for my maps app. I enjoyed seeing lots of things despite the bitter cold. I did more than what I originally planned or expected to do, despite being solo, or because I was solo! 🙂

Mass Transit in Chicago is so much cheaper than parking your car.

Chicago in winter

It is always nice to have a travel companion who is up to the exploration, hiking, or walking, as much as you are, or have the enthusiasm and energy as much as you have. But if need be, we can travel on our own too.

Things to do in Chicago during Winter Season:


How about you? Have you traveled solo? What were your experiences and challenges, and what are your advice to solo travelers?


About Author

Born and raised in the Pearl of the Orient Seas, now living in the United States; she is a traveler, road tripper, outdoor camper, and field photographer.

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