Chicago. The third most populous city in the United States. The first large metropolitan area that I have visited since I began my journey. Chicagoland. Land of lots of people.

I have visited the #1 and #2 most populous cities in the US in the past – New York and Los Angeles. As a matter of fact I lived in the LA metro area for 7+ years, but that was a while ago. And I didn’t have to drive when I was visiting New York. So I had forgotten how bad big city traffic can be. Especially at rush hour. Ugh!

On my quest to visit as many co-workers as I come across in my travels, I connected with Dave who lives in Chicago proper. We co-worked on Friday (which happened to be my 2 year anniversary with the company, but I totally forgot about it so we didn’t celebrate) at his house, which is in a quintessential Chicago neighborhood. Which means the Chicago ‘L’ runs nearby, there are lots of great restaurants within walking distance, and it just has that cool major metropolitan neighborhood vibe. Not something I am used to and It was fun to experience.

In order to get a good overview of the city we did that most touristy thing in Chicago – we took a boat tour. An architectural boat tour to be exact. For about 75 minutes we cruised the three branches of the Chicago River and got the lowdown on the buildings in that area. Cool. Interesting. One of those things you do once and are good. But a great way to quickly see the heart of the city and learn a few things.


Then we walked for a while. Not that we didn’t walk before. Cause you do a lot of walking in Chicago. Good thing I was wearing real shoes as I am sure we exceeded my 5 mile rule for wearing flip flops.

We walked the bike/walking path that parallels famous Lake Shore Drive and came across the mess that is known as Lollapalooza. You know, that huge annual music festival that is help in Chicago. Apparently during the weekend I was there. Exactly in the part of the city where I wanted to explore. Sigh. It’s all about the timing…

Moving Quickly

Chicago has a great network of bikes that you can rent (bike share) for a period of time. Called Divvy bikes these cool blue bicycles are stationed strategically throughout the city. You walk up, work some magic via the kiosk (that involves your credit card, of course) and off you ride.

The first kiosk we tried was the closest to Lollapalooza. Mistake. I used my incredible counting skills and counted bodies ahead of us, number of bikes left at the stand, and figured we were screwed. As in not getting a bike. So we fought our way through the throngs of people to a nearby Divvy station. Where there was no line and plenty of bikes. So off we went.

The idea was to head towards the John Hancock Center, or more specifically the Signature Lounge on the 96th floor. Great views. Great conversation. And a great way to wrap up the day and trip to Chicago.


I was still staying at the Blackwell Forest Preserve which is about a 35 mile drive from Dave’s house, or about 35-40 minutes without traffic. Maybe less. Cause Chicagoans haul ass when they drive. The speed limit of 55 mph is just a suggestion. If you aren’t doing closer to 80 you are a road hazard. That is until traffic stops. Which is does. During rush hour. Which I happened to be traveling in on my way back to my house Friday. It took close to 1 hour 45 minutes to make the 35-40 minute drive. Because of the nightmare rush hour traffic. I really hate traffic!

Other than the traffic, I have a great time hanging out with Dave in Chicago for a few days. While I only saw a small fraction of what the city has to offer, I loved what I saw and can’t wait to come back and spend more time exploring. But it was time for me to move on and spend a much deserved week in the middle of nowhere. With no plans other than to relax.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s