After three long days of driving, we finally reached Chicago. We had a great time catching up with my brother’s old college friend, but we were quickly reminded to get at least a few hours of sleep before we had to leave again in the morning to continue our journey.
We left quite early in the morning as we’re planning on meeting up with some more friends in the suburb of Toledo for lunch. I wanted to make sure we could get out of Chicago without getting caught in morning commute, and we also wanted to make one more stop to complete our Route 66 journey. We started the journey three days before at the plaque near the beach of Santa Monica, CA, that marked the west end of Route 66. We thought it would be appropriate to also stop at the east end of Route 66 in Chicago.
Both my brother and I had been to Chicago many times, and we were somewhat familiar with the downtown Chicago area. But neither of us ever noticed seeing any sign there that marked the east end of Route 66. I looked through guidebooks about Route 66, and I found information about either it’s located at the intersection of Michigan Avenue and Jackson Street, or it’s somewhere near the nearby Grant Park. So we decided to just drive to that area, park our car, and perhaps walk around a little bit to find the marker.
We parked at the underground parking on Michigan Avenue nearby our destination, and we were greeted by something unexpected that we should’ve known and anticipated better. When we got out of the elevator from the parking garage, we were greeted by a cold and windy Chicago autumn weather. Here we were, wearing light jacket and sweat and sandals. That was fine when we were traveling in California and the Southwest, but not in Chicago. So my brother’s comment was about finding this Route 66 marker quickly and then perhaps get hot coffee and leave.
We reached the intersection of Michigan Avenue and Jackson Street, and we couldn’t find that end of Route 66 sign. The only other info I had said the official east terminus of Route 66 was the Grant Park. Well, that’s not really helpful as Grant Park was quite a large park. I told my brother, ‘how about walking around the park a little bit to look for the Route 66 sign’. My brother said, ‘why don’t you go ahead and do so; I’ll just wait at the coffee shop around the corner because it’s way too cold to walk around outside.’ So I did go to Grant Park and walked around looking for the Route 66 sign, but couldn’t really find it. Finally I ran out of time (and it was getting too cold out there), so I decided to just cut my losses and took the photo of the Chicago skyline to show that we did reach the east end of Route 66. It would’ve been nicer to bookend the trip with another photo of a Route 66 plaque, but unfortunately this one would have to do.