Below is a one-day Chicago itinerary brought to you by DetourOn. You obviously do not have to follow it exactly, but think of it as a rough outline. Log into the DetourOn Planner to make your own itinerary. There you’ll find many more things to do in Chicago in a day. Quick word of caution: This is one person’s account of spending one quick day in Chicago on a budget.
Friday in November. That’s the day I visited Chicago. Temperatures were above freezing with moderate wind chill. They say those are good conditions visit the Windy City. I don’t know who “they” are, but I’m fairly sure conditions could be better. I only had one day to visit Chicago and it just so happened to be in November. The following is my account of things to do in Chicago in one day (check out the itinerary at DetourOn).
My day started at 10am underneath an elevated platform of steel rails. This was the “L”, it quickly dawned on me, the city’s equivalent of the metro. Fun fact: Unlike a subway, the L is mostly “el”evated. My trusty city guide was a local friend I met in the western United States a few years back. She would show me the most important things to see in Chicago in one day.
Looking for Route 66
I hadn’t researched anything about Chicago. The only thing I knew I wanted to visit was the beginning of the Route 66. After all, as the great Chuck Berry taught us, it “winds more than 2000 miles from Chicago to LA”. I also wanted to eat a deep-dish pizza and a hot dog, but we’ll get to that later. As it turns out, nobody really knows where Route 66 officially starts. We downloaded this trail map of the supposed route, then followed it word for word like a scavenger hunt.
Finally, we arrived at the corner of Jackson and Michigan and saw a sign reading “END of Route 66”. Needless to say, I was infuriated! The song clearly states that the route winds from Chicago to LA. So clearly it begins in Chicago and ends in LA. There is no going back, so how could there be an END sign? I continued making a fuss over this subject to my friend throughout the entire day. I just could not get over my disdain to the END sign. I’m not sure how she managed to stick with me throughout the day.
To get my mind off the END, my guide suggested going to see the Lake and the city parks nearby. Of course I heartily accepted. After all, I am in Chicago for only one day. I came to see the entire city, not just a little sign. So off to the Lake we went. It seemed more like the Ocean to me.
My friend pointed to a tiny island way in the distance with a needle sticking out of it. That’s the famous Chicago Water Crib, the location from which the city pumps its drinking water. I was taken aback. Suddenly I realized that I was looking at a huge lake, not the ocean. A fresh-water lake! I suppose it took a while for the light bulb to go off. I had to keep reminding myself all day that I was drinking lake water. Chicago is a city in the middle of the United States, not sitting on any salt water shore.
Chicago parks and fountains
From the Lake we turned back toward the city and passed the impressive Buckingham Fountain. It was dry due to it being the winter. We continued through Grant Park, known for Lollapalooza, to Millennium Park. This is the location of the famous Chicago bean, also known as Cloud Gate. This smooth metal structure in the shape of a kidney bean is as big as a two-story house. The most interesting part about it is the reflection of the sky, the skyscrapers, the ground, and the people taking pictures of it from all directions. Hours could be spent taking crazy pictures of and from this structure.
100 photographs later, after the initial shock and excitement over the Chicago bean, we continued moving toward a Face Fountain in the southwest corner of the park. This was also dry due to the winter season, but the face showed on it nevertheless. Officially known as Crown Fountain, this is a blown-up composite video of a face the size of a building. The picture changes every few minutes and spits out water from the face’s mouth. I presume it is really cool to see when water is actually flowing.
Back to Route 66
Moving on back toward downtown, my friend had the bright idea of telling me that we’re going to look for the beginning of Route 66 again. I had completely forgotten about it, what with the lake and the bean and the spitting fountain. Now my mind was about that dreaded road again! I managed to keep my composure and suggested we get a hot dog afterwards. Then I proceeded to explain that the Route 66 had always been driven from Chicago to LA. All documents about the road always explain it in the westward direction. See this great Route 66 map series collectibles item. It is never documented eastward, and therefore it is impossible to have an END sign.
Beginning of Route 66
Soon we arrived at the intersection of Adams and Michigan and lo and behold there it is, the BEGIN sign! I shut up and took some pictures and we walked in silence to Kim and Carlo’s stand. They have THE BEST Chicago-style hot dogs! We continued our city walking tour downtown past big buildings. Only from time to time did I raise my voice to say something about the END sign. My friend silently put up with it.
FYI: It turns out that there are a few “Begin Historic Route 66” signs on the corner of Adams and Michigan. Disgracefully, no one seemed to pay much attention to them the day we were there. For more info on the entire Route 66, check out Road Trip USA and their great Route 66 guide book, updated in June 2019.
Beginning of the Historic Route 66 – corner of Adams and Michigan Cloud Gate aka the Bean
Buildings of Downtown Chicago
Other sites we saw along the way in Chicago were the Chagall Mosaic by the Chase Building. Lean back against the building and look up. You’ll have the impression that it’s going to fall on you. For your information, this is the building where Wait Wait Don’t Tell Me, the NPR News Quiz is recorded each Thursday. Unfortunately, I arrived too late Thursday night and missed the recording. Instead, I had THE BEST deep dish stuffed Chicago-style pizza at Giordano’s.
Following the Chase Building, we walked to see other buildings nearby with cool architecture. Some were designed or renovated by Frank Lloyd Wright, such as the Rookery Building. We walked by the Sears (or Willis) Tower, then bought a cupcake from the A Sweets Girl truck. It just happened to be downtown that day. We ate the cupcake at Union Station while looking for coffee from a non-franchised company. Failing to find that, we followed the Chicago Riverwalk toward 360 Chicago, formerly the John Hancock Center. Of course, we made a small detour through more buildings downtown until we finally fell upon the magnificent Café Integral, located in the hotel Freehand Chicago, for a much-needed non-chain coffee break.
With a renewed boost of energy, we made the final stretch through the Magnificent Mile to arrive at our final stop, Bar 94 at 360 Chicago. We took the elevators to the bar on the 94th floor and enjoyed the view from the top. For some unknown reason, we descended before being served any drinks even though we were both completely dehydrated at this point.
As we waited for the “L” to take us back to our starting point, I asked, “Which lake did we visit this morning?” I would like to thank her for putting up with me for the duration of my short stay in Chicago. It must have seemed like a really long time for her. And I’d also like to thank her for not laughing too hard when she answered that we visited the shore of Lake Michigan, the second biggest by volume of the Great Lakes.