Chillin’ in the Windy City: A Chicago Travel Diary

Happy Holidays everyone! I am back with a new travel diary.

This Fall Quarter was a mess with me all over the place, trying to balance everything. If you didn’t know, I am actually in my last year of college! This quarter was dedicated to finishing some of my last general ed classes (thank god, I passed chem), starting my term as Kaibigang Pilipin@’s president, hustling through two jobs, and simply, enjoying my last year of school. Nonetheless, I survived and here I am!

I have been anticipating Winter Break for the longest time. Heck- once week two of the quarter hit, I was ready to leave! I usually don’t do much during the holidays except fly back home to the Bay Area, visit family, and relax. However, this Winter Break is quite an eventful one! I am so thankful I have the chance to travel this holiday season. That travel bug in me is still alive and thriving!

I’ve been itching to travel ever since the school year started. With each weekend packed with extracurriculars, homework to do, and exams to study for, I couldn’t find time to relax and plan a weekend getaway. During a random, fateful day studying for midterms, I bumped into my great friend Jake at a local boba shop. After catching up about our past summer adventures, we both knew we wanted to get out and travel. Couple boba drinks after and that conversation resulted in two roundtrip tickets to Chicago! I don’t know what we were thinking that night, but I’m glad we decided to take the plunge and go for it.

I haven’t experienced snow since my last Lake Tahoe trip probably fifteen years ago. I grew up in San Francisco, so I’m used to dealing with chilly, bipolar weather. Chicago weather was going to be a whole new playing field. Weeks leading up to our trip, I read several articles about Chicago in the winter time. Let me tell ya— the weather is horrendous with frequent snow storms. You see, I wasn’t ready at all and didn’t know what to expect. With a duffle bag packed with a puffer coat, teddy jacket, scarves, gloves, and boots, we flew out to Chi-Town straight after our finals!

When we arrived there, we were surprisingly greeted by a cool winter breeze. It didn’t snow at all during our trip! However, if you do plan on visiting Chicago during this time of year, expect temperatures to average around the mid-thirties to low forties. Nonetheless, we had a great time exploring the city. This was both our first time actually experiencing winter weather at its prime. As Californians, specifically San Diegans, we’re blessed with perfect sunny weather all the time. I was grateful to experience something new!

Jake and I visited all the iconic spots like Cloud Gate at Millenium Park and Portillo’s Hot Dogs, along with local hang out spots like the Lincoln Park Zoo. We were able to rock cute winter fashion and explored the Windy City by public transportation. Our Airbnb was nestled in the perfect location for tourist travels. Everything was either a 10-minute walk or a very short bus ride. We had full access to yummy food, great bars, and iconic tourist attractions. We had an amazing trip and I can’t wait to visit Chicago again– when it’s not freezing cold outside, haha.

Here are some pics to sum up our time in Chicago:


I would most definitely visit Chicago again. Shoutout to Jake for being a gr8 travel buddy. Maybe we’ll come back for Lollapalooza? 😉

Stay tuned for my Utah & Arizona Travel Diary. Can’t wait to share all my winter travelz with y’all!


kaithleen1 (2)

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