A Beautiful Day in Chicago with Old Friends

Lake Michigan, from the beach in Rogers Park

As I embark bright and early tomorrow morning on Route 66, today was a day in Chicago to meet up with old friends – and to get ready. It started with a nice morning with my mother, and then after lunch I used the (wonderful) CTA system to visit my old friend Jon – who I hadn’t seen in about 4 years. Jon and I have been great friends since we were about 6 years old – as we lived across the alley from each other in Hyde Park. He now lives with his wife and 6-month-old baby in Rogers Park, just a couple blocks from the Lake.

The attached photo is a pier from Rogers Park, looking south towards the Chicago Skyline. The thing about spending your whole life in Chicago is you can never really get to know some neighborhoods. Rogers Park is at the northernmost point of the City (next to Evanston), and I’d never been to its lakefront because Lake Shore Drive ends a few miles south. With no highway along the lakefront, it is probably one of the most underrated parts of Chicago. A real treat, and I was pleasantly surprised to discover it today.

Next, was time to go back to O’Hare and pick up my rental car. I’m using Dollar Rent-a-Car, because they have the best rate. And while I’m not thrilled with the one-way drop-off fee, the trick about rental car companies is that those who don’t charge a “drop-off fee” simply inflate the base price for its one-way rentals. Even with the drop-off fee, Dollar is still cheaper than the other companies. The clerk convinced me to throw in an extra $75, and get a Jeep Compass for the trip. While I normally wouldn’t do this, I’ll be driving through Arizona and New Mexico – so I figured it was worth the slight extra cost. I’m just hoping the gas mileage will be decent (what with prices!)

With my car in hand, I drove to Ukrainian Village to have dinner with my friend Vasyl – who I hadn’t met in 15 years, after we worked together on Dick Durbin’s campaign way back in 1996. It was really great to reconnect, and talk politics. There’s so much about Chicago politics that I haven’t been keeping up with, and I haven’t really kept in touch with people from my Durbin days. Vasyl and I had reconnected on Facebook. Then, I went to Wicker Park to have drinks with my friend Jenn – who had gone to Maine for the “No on 1” campaign. I’ve been going to Wicker Park since I was 10-years-old when an old school friend lived there. Back then, of course, it wasn’t the crazy hipster gentrified neighborhood it’s become – and walking around Wicker Park on a Saturday night was certainly a culture shock for me. Chicago has definitely changed, indeed …

I’ve had a great day, but am far more excited about tomorrow – when I take off on Historic Route 66, embarking on a road trip I have only dreamed about for years. I promise to bring insights from the road. But today was not about offering insights … it was just about re-connecting with old friends, who I spend way too many years not seeing …

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