Chicago Winter 2025

This is a travel blog post of my Chicago trip in the Winter of 2025. Chicago during the winter is extremely cold, below freezing point temperatures. It’s brutal especially coming from someone born and raised in LA. At the minimum to be comfortable in below freezing weather, you’ll need a warm jacket, pants, beanie, gloves and dress in layers.

March 9, 2025 by Kazu Fujimoto

LAX to ORD

Took an Uber to LAX. Recently signed up for the United Mileage Plus Business Card which allows me lounge access to locations globally. Lounges are more comfortable and provide food/drink. Pretty worth it if you do the math long term. Highly recommend for other small business owners. If not a business owner – the standard club one comes at great benefits as well.

Did some work at the lounge, reviewed resumes, evaluated business strategy.

The flight to Chicago from LAX was about 3.5 hours. Overall pretty smooth, but did experience some turbulence when above the Colorado Rockies.

The Westin Inn – Michigan Ave.

Stayed at the Westin Inn on Michigan Ave. The room was pretty standard, but opted for the view of the Michigan Ave, which was an extra. The hotel is located in a convenient location right next to the 360 skydeck and riverwalk.

Museum of Contemporary Art (MCA)

Went to the Museum of Contemporary Art (MCA). The exhibit seemed lackluster to me, but found some pieces that I thought were interesting. Generally when I go to Museums – LACMA, Art Institute of Chicago, etc. – I generally get drawn in and mesmerized into the art pretty easily, but the pieces at the MCA didn’t do really do it for me. To each their own.

360 Skydeck

The 360 Skyjack was beautiful and gave a nice which overlooked all of downtown Chicago. At the 96th floor of the building, this’ll definitely give you a wide overview. Went around sunset time, it was pretty packed, but the crowd started fizzling out after the sunset. Great place to take some pictures, relax, and you can even opt for the sip and watch option where you enjoy a drink, sit down, and take in the view.

STK Steakhouse – Chicago

For dinner, went to STK Steakhouse, which is a moderately upscale dining place with somewhat of a party atmosphere. The restaurant had a DJ in a booth and was playing house music, which gave a nice vibe, if you’re into that thing. It’s nothing like a typical traditional steakhouse or even a typical upscale one with the fancy silverware and the dimly lit lighting. It’s a fun one to go on a date or with some friends before some big event like a concert or club.

Biggs Mansion

After the restaurant, went to Biggs Mansion to smoke a cigar. The cigar selection seemed standard. I opted for the Arturo Fuente Reserva Don Carlos, which is one of my favorites. It was my understanding that the facility provided glasses and ice, but that was the private members only area which you need to get day passes for. The interior of the members only area is very traditional and standard of a cigar lounge – leather chairs, fireplace, warm interior, old fashioned interior design. Great place to hang out, smoke a cigar, get some work done, do some networking, or think some incredibly insightful thoughts.

A Midsummer Nightdream – Chicago Shakespeare Theatre

The next day, went to see A Midsummer Night’s Dream, which is one of Shakespeare’s most famous plays. The performance of The Midsummer Night’s Dream, seemed a bit lackluster. Although there was a ton of effort in the energy and passion that the individual play actors, the production just didn’t seem to do it justice, especially at the relatively high price point ($100+). This is just my commentary, so please don’t be upset by this, this is just simply what I thought.

The plot of the play revolves around 4 main threads:

1. The Lovers – Hermia, Lysander, Helena, and Demetrius (Love Triangle)
2. The Fairies – Oberlon & Titania
3. The Mechanicals – “play within a play”
4. The Royals – “involvement by the audience”

The performance also took an attempt to modernize the play with current day culture, which some may enjoy, but I personally didn’t.

Overall, it was nice to see, even if the production was lackluster, as the individual characters all seemed very passionate and energetic in their roles.

Volaire

Volaire in my eyes is a go-to restaurant for many looking for Italian comfort food, or looking to enjoy an evening out with some friends, at a moderate cost. The menu wasn’t too expensive. I opted for the lasagna, which I thought would’ve been a good and safe choice, but it was nothing spectacular and pretty lackluster as well. Their seafood pasta options seem to be the more popular choice.

ORD to LAX

A straight forward uber back to the airport from The Westin, hanging out at the United Club lounge at the ORD airport, then boarding the flight and heading back. For whatever reason, the flight landed earlier than anticipated, which I was not used to. As a result, this gave me time to make it to my in person tax appointment that I had on Sunday, which I was going to attempt to call into or attend virtually.

Closing Thoughts

Chicago in the wintertime is cold. Don’t recommend unless you’re going to see some friends, family, or loved ones.

I am however thankful that I do get to travel a lot, and I attribute it to taking care of myself financially.

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