Live well. Eat well. Travel well.

Over the weekend I had a chance to explore Chicago at night. I was only staying overnight 40 minutes away from downtown so why not check out what downtown has to offer since it was my first time in Illinois.

Living around San Francisco Bay Area, I always compare downtown cities to SF. Chicago was way cleaner… better! As I stepped out around 9:30 PM to experience the TILT in 360 Chicago or also known as The John Hancock Center, it was a chilly low 40s Spring weather. Bought tickets for 10PM but got there 30 minutes early so I took in the view of the city 94 floors above.

The TILT experience is a thrill ride that is about 2 minutes long. You stand while holding on to the rails then the glass tilts so you get a glimpse of the city facing down… well tilted. Unique experience that I won’t mind trying since some skyscrapers offer thrill experiences but you are out in the open. At least this one you are inside the building.

I went with a friend and we had a drink after to relax my shaking legs while we enjoyed the city lights below us. As they were preparing to close down the attraction, we headed down to beat the line.

We walked towards the river walk and felt safe walking along the downtown streets where the shopping centers were (compared to walking in SF where you’ll find homeless folks on streets either laying or doing drugs, in addition to being extra careful not to step on pee and fecal matter). I found it to be a nice walk along the streets lined up with pretty tulips.

After about 20 minutes of walking, we reached our destination. We walked to the other side by the bridge and stopped to admire the view and the colorful lights reflecting the river.

Not knowing what to do next since most shops are closed, we decided to walk towards the Millennium Park to see if we can get a glimpse of The Bean, although we already know that we might not see it due to the ongoing construction through Spring 2024. It was a short 12 minute walk.

We found ourselves not only cold but also needing to use the restroom. We only noticed hotels and convenience shops (Walgreens or 7/11) where we were walking. As I thought of just going in one of them, we saw Elephant & Castle British Pub. We decided to go inside to hit 2 birds with 1 stone… potty break then get shots to warm us up! It was perfect!

We continued our walk along the street where the train runs above us. This is where we first noticed homelessness where some folks are laying on streets wrapped in thick blankets.

There were not much people walking at this point and it was almost midnight. We crossed to see the park and went back to where the theaters were.

Either we weren’t really looking hard or there weren’t really much happening in downtown on a Saturday night. When the Chicago theater lights were turned off, we decided to get our Uber ride back to where we were staying. It was a challenge at first since about a handful of Uber drivers who accepted our request cancelled on us. We realized that we were on the main street where the subway entrance and exits were and has signs that says “No Parking. No Stopping. Tow-Away Zone.” So we walked a bit further towards Macy’s and finally one Uber didn’t cancel but had to park across the street where he can wait.

Overall, I thought it was a good 3 hours spent in downtown that was chill. Next time I’m in town, I will take a walk during day time and experience the bustling Chicago downtown.