12 In Liz Travels: Route 66

It Has Begun!

Begin at the beginning…

Today Dash and I actually took the first steps on Route 66. And we started, as of course we must, with breakfast at Lou Mitchell’s, a classic diner on Jackson. It was packed and with good reason: Great food. And we got free donut holes. I haven’t had donut holes in…well, a really, really long time. They were scrumptious. I would have been happy to have just a box of those for breakfast.

You can’t drive Route 66 and not stop at the “begin” sign. So we drove down to Michigan Blvd, parked only slightly illegally, dashed to the sign, got a kind Chicagoan to take out picture, and dashed back to the car before we were ticketed. As you can see from the picture, some people can’t help but leave a “sign” of their own that they have been on the Route.

The next destination, for two admirers of the work of Frank Lloyd Wright, was the Wright home and studio in Oak Park. But of course, we first had to get lost.

Lost under the CTA

You see it in every movie filmed in Chicago, practically: the car chase under the Chicago Transit Authority (CTA) “el”–the elevated train. We got ourselves trapped under the “el” on Lake Street. If you’ve seen those movies, I’m here to tell you the rattling and banging of the “el” overhead is actually louder, and the space under the “el” is narrower. Thank goodness we weren’t being chased. And thank goodness we weren’t driving the 1956 Buick convertible that stars in The Route 66 Steal.

By time we got out from under the track we were utterly confused, but somehow mostly on the right track. With only a few more wrong turns–and only a few expletives for the dispassionate electronic phone voice that wouldn’t talk to us when we needed her, we got there in time to take a walk around the neighborhood and see a bunch of Wright-designed houses. I’ve only included one here–no need to torture you.


I haven’t spent a lot of time in Chicago before, so have been awed and delighted by the vast variety of neighborhoods, and the dramatic way the city can change from block to block. I visited Chicago Costume, in the Lincoln Park area, as research for The Illinois Caper, and passed through a tunnel of old trees in front of old shoulder-to-shoulder homes of stone and brick, some of which were almost gothic. Then, cross a street, and it was all slick brick-fronted and boring buildings.

When planning this trip, Dash found us an Air B&B in the Pilsen neighborhood, an area once populated by my genetic “peeps”–Bohemians. (Those from Bohemia, not those who like to live a madcap lifestyle, though I guess I fall into both categories.) Over time, it shifted to a more diverse, though largely Latino population. The walls are covered with murals, and there are a bunch of restaurants within walking distance. We tried La Luna, and had great fish tacos. Pilsen is a neighborhood that has seen some hard days, but is now filling with carefully updated and cared for homes.

Returning downtown from Oak park, we avoided the “el” by taking Chicago Ave. A great choice, because it introduced us to a a variety of other neighborhoods, leaving us wishing we could stay in Chicago longer so we could move from one to the other and get to know each.

Fighting our way to Navy Pier

We had a great drive until we got close–we thought– to our destination of the Navy Pier. On a Sunday. A beautiful, sunny Sunday when apparently everyone in Chicago had the same idea. (We will not even discuss the cost of the parking…) We got stuck in horrific traffic, and then it was all worthwhile when Dash spotted the bunnies on the bikes–and managed to get a picture of them!

Having gotten to the pier, we took a ride around the harbor of the enormous and gloriously beautiful Lake Michigan. I was raised around the Great Lakes so this was coming home. I’m afraid I only heard part of the description of the city skyline of Chicago. I was steeped in amazement that we all travel thousands of miles to see inland seas like the Mediterranean, when we have these unparalleled bodies of fresh water snugged in between the US and Canada. I have promised myself I will come back and spend more time on the lakes.

We followed our google map-lady (once again speaking to us) out of the Navy Pier area, which was fortunate because the path out, as native Chicagoans well know, flows under the city through a maze of subterranean versions of the streets above. It was, for those of us used to Oregon, a bit of a scary experience. Just very glad I don’t do it every day.

It was a full day. And I’m sure we could spend many others here, but the road beckons, and we are off to Joliet in the morning.


P.S. For subscribers following the adventures of Kat and Tish (definitely NOT modeled on Dash and I), another chapter of The Illinois Caper has been posted at The Route 66 Steal site.

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  • Reply
    June 6, 2022 at 8:18 am

    Before today, I didn’t know that Route 66 started in Chicago. Maybe I was getting it mixed up with the Oregon Trail. Ha ha ha! Nice photos!

    • Reply
      Sharon Thompson
      June 6, 2022 at 6:18 pm

      And I guess if you start in Santa Monica, you could say the Route starts there! All things are relative.

  • Reply
    Lori Murphy Cole
    June 6, 2022 at 10:26 am

    Wowzy, what a Chicago adventure!!!!

    • Reply
      Sharon Thompson
      June 6, 2022 at 6:17 pm

      Chicago is a busy place! Way too much to do in two days. Would love to spend more time here, though!

  • Reply
    Gary C Gugler
    June 6, 2022 at 11:36 am

    I used to eat at Lou Mitchell’s when I lived downtown in the early ’80s. Downtown Chicago’s roads are a crazy mess, but that’s where Route 66 began.

    • Reply
      Sharon Thompson
      June 6, 2022 at 6:16 pm

      I’d eat there only for the donut holes!

  • Reply
    June 7, 2022 at 2:08 pm

    Yaaaaa, the donut holes sounded divine…

  • Reply
    June 7, 2022 at 2:09 pm

    I was born in Cook Co but moved soon after

  • Reply
    June 8, 2022 at 6:01 am

    I so enjoyed reading the first of what I know will be just the beginning of a string of fun filled adventure stories! Please give Dash a big hello
    from one of her Tauck Tour friends. Have a blast, safe travels.

    • Reply
      Sharon Thompson
      June 9, 2022 at 5:21 am

      Thank you, Diane! From both of us. Liz

  • Reply
    June 10, 2022 at 2:47 pm

    I saw a man in a restaurant in Silver Spring, Michigan with a ROUTE 66 T-shirt. I would have taken his picture but it would have been a little distracting to him and his friends. I think the location on the back was somewhere in Arizona. In naturally thought of you and Dash!

    • Reply
      Sharon Thompson
      June 11, 2022 at 5:13 pm

      Yes, Claudia, that might have been a bit awkward! But thank you for thinking of us! Love, Liz

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