A Chicago October Business Trip

In October 2026, I took a business trip to Chicago. I was visiting a Google Cloud Security event similar than I did a few years ago in New York City: https://davidcrosstravels.com/2018/03/23/new-york-city-in-the-winter/

The fall weather was pleasant, making it perfect for exploring downtown Chicago on foot through its safe, walkable streets. During my walks, I enjoyed wonderful skyline views and vibrant cityscapes.

The city offered plenty of fun sights and local festivities.

I got to check out Chicago Oktoberfest Nation with its festive displays and decorations setting a cheerful autumn mood.

Another highlight was walking near the Adler Planetarium Which is a short Uber ride away from the downtown area but definitely worth visiting.

They have a pretty good presentation of the skies and stars but it’s nothing like the sphere in Las Vegas!

You may want to check out the previous posting and watch the video: https://davidcrosstravels.com/2023/12/24/what-is-new-in-las-vegas/

The best time is to visit at night where you get stunning views across Lake Michigan under clear skies.

While strolling around the city, I also noticed quirky urban details—like an abandoned building with funny delivery stickers plastered all over its glass front doors.

Before heading to a Google business meeting, I made time for breakfast and local treats.

I picked up fresh donuts from popular local spots rather than standard chains like Dunkin..

and relaxed at lunch with full table service at…McDonalds!

Is this Mcdonald’s trying to upscale?

As the sun set, the illuminated city skyline provided a gorgeous evening view across the city center.

To kick off the big meeting day, I grabbed a classic hearty breakfast at The Original Pancake House

I have to admit the food was pretty good! But I’m a born and raised mid westerner…