Chicago November 2019


There were two significant takeaways from my first trip to Chicago :

(1) It is a pretty cool city with an awesome downtown area / architecture.

(2) I don't like cold weather.

Both of these items will come up in different forms one way or another throughout the remainder of this post. One large significance about the cold conditions is that I was less inclined to pull out my phone and take photos of the surroundings. I powered through in most circumstances for the sake of this art but don't expect the plethora of photos like previous posts. I ask for you instead to use your imagination...horrible, I know.

It is actually strange to think that I've never been in Chicago (aside from a short layover years ago to New York) since travel has become a significant part of my free time but I'm glad it finally happened. My dad is from Chicago so I was inevitably raised a Bears fan but we never made a family trip to the city growing up. We were somehow able to organize this recent trip so that not only my parents could make it but also my sons, and my sister / her family.

Whenever it gets close to my scheduled trips I am checking Apple Weather and Weather Channels apps like a heroin addict. As the days inched closer it wasn't looking good for reasonably warm weather and the trip definitely didn't disappoint on that factor. Each day beforehand the forecast continued to shift between possibilities of snow and/or just downright cold weather. When I conveyed the prospect of snow and 20 degree weather to my sons my eldest, in the greatest of wisdom, told me he was going to wear shorts / that his legs don't get cold. It was not until numerous times pointing out the absurdity of this statement that there was agreement to not only purchase pants (which really is not a necessity in Phoenix when you compare it to other cities) but also a thick jacket. I figured that purchase of such items actually has triple purpose as not only would it be used in Chicago but also for our upcoming trip to Munich next March and to Iceland in July. That being said, the average temperature for Munich at the beginning of March / end of winter (which is surrounded by the Alps, mind you) is higher than what we experienced most of our Chicago trip. Go ahead and wrap your head around that one.


So, we are packed with our bundles of clothes and fly on a relatively early flight to Chicago. On a side note, the rest of my family took some ridiculously early 5am-ish flight from Portland the same morning. We either had a choice of a 6am or 9am flight. 6am did not happen. You may or may not know but there are two airports in the Chicago vicinity with neither of them being especially close to downtown. Depending on what airline you choose the decision is made for you as to which one you land at but my understanding is Midway is the smaller of the two (O'Hare being the other). Since we flew Southwest we landed at Midway. I always like to point out if I like certain airports even though it is somewhat pointless since most cities only have one airport but I will continue my thoughts on airports nonetheless. I wouldn't say Midway is a horrible airport but the layout and amenities leave something to be desired. The strangest thing was that they didn't even have a Starbucks in the terminal...I note the strangeness of this mainly because there seemed to be a Starbucks every 100 feet in the downtown area and they are about to open the largest Starbucks (a Reserve Roastery) in the world. Also of note was that when we landed we seemed to be at the furthest possible point in the terminal to getting out of the airport. We elected to take the train to downtown. I am always about trains and/or subways if they are accessible as I hate driving and it is usually quite a bit cheaper - to give comparisons, the 3 of us taking the train to downtown was $9 while a Lyft/Uber was around $30, not including tip. The biggest issue with the train from Midway is that you have a bit of a walk from the terminal to get to the station - adding that to the long walk from the gate to the airport exit, it probably took about 20 minutes to get from our gate to the station. Granted, not all gates are so far from airport exit. Another reason I specifically chose the train versus a Lyft/Uber is that the commute time to our hotel was showing almost the exact same time - obviously, the time factor is the main reason I would choose a share ride over mass transit.


The grumbles of the cold were almost immediate from my youngest son after we exited the train station and started our pretty short walk to the hotel. We stayed at the Warwick-Allerton, which was a really nice location in relation to all of the things we visited on the trip. It is right off Michigan Avenue, which more or less reminded me of 5th Avenue in New York. The hotel itself was decent, as long as you understand it is a very old building. The room layouts were a bit bizarre and the elevators always seemed busy but it is otherwise a reasonable choice for what seemed to be a nicer, more economical hotel in the area.

I tried to be relatively hands-off on organizing this trip since it was more for my dad / a family affair but I somehow still ended up being the organizing guru...


One of the most important things about our hotel location (which I was not aware of until we got there) is that it was across the street from a ramen restaurant (Ramen-San Deluxe). As you likely noted from past posts, the appreciation of ramen in Tokyo carried over to the states for me and my sons. Although I found the ramen vegetarian broth a bit bland, their avocado tempura roll was awesome, as were the eggplant fries.

We missed the opening of this awesomeness by a week. Next time...next time...

The first evening we went to the Willis Tower / Skydeck. We purchased tickets online beforehand for that specific day but I noticed that the tickets actually have flexibility / can be used within a week of the date you choose. It is always nice not having a timed entry to attractions. It was worthwhile seeing the night view, most notably to see the huge blackness that is Lake Michigan. It is crazy just how immense it is and to think it is not even the largest of the great lakes. It seems inevitable that going to the Willis Tower would get comparisons to visiting the Empire State Building and/or Rockefeller Center in New York. It's probably not fair to make such comparisons but I'll do it anyway. I very much preferred the New York experiences, mainly because I liked the actual buildings a lot more than Willis Tower. The buildings in New York also give the option of going outside, which may or may not be of interest to you. That being said, Willis Tower does offer an experience called "The Ledge" which is essentially walking into a clear box protruding from the side of the building so that you feel like you are suspended in mid-air and have a view 103 stories straight below. I can't speak to the worthwhile-ness of this as I wasn't having such things but it definitely seemed popular as there was a separate, long line to go into one of the ledges...I believe there are 3 total.

View from Willis Tower

After Willis Tower we headed back towards the hotel to have our first Chicago Pizza experience. We initially tried to go to Giordano's, which was recommended by multiple people in the area, but when we found out there was a 1.5 hour wait we headed to Gino's East down the street. I can honestly say I've never had a pizza quite like it. The crust is deep-dish and cornmeal based, which gave it a robust flavor. It was a pretty long wait to get the pizza but it really was worth it.

The next day's major happening was the Chicago architecture boat tour. Note that this does require advance tickets. We used First Lady Cruises but it appeared that there were a handful of different options for boat tours so you'll likely want to do an internet search to see which is the most fitting for your trip. I may not have mentioned it previously but it was cold. Due to the wind chill my youngest son had no desire to sit on the top open area. The rest of our group (and pretty much the rest of the people on the boat) went to the top area while he and I sat in the back of the enclosed section. The tour lasted about 90 minutes and consisted of going up and down the river with commentary about the surrounding buildings. Downtown is a pretty cool with the juxtaposition of the low river and towering high-rises, which was one of my favorite aspects of the city.

After the boat tour we headed further South (by foot). I should probably point out that due to the short duration of our stay (which actually ended up being a little shorter than expected (I'll address this later)) we really didn't head outside the downtown area.


In heading south on State Street we passed by the famous Chicago Theater, which is also infamously known for being the location where John Dillinger was gunned down. I didn't think to look the theater up prior to our trip but noticed on banners as we passed that they offer tours. I'm sure you've gathered by now that tours of old buildings / architecture is something I always look for in cities so this would have been something of interest for me had I known. It is definitely on my "to do" list when I head back to Chicago. Another architecture-related place I want to visit is the Frank Lloyd Wright Robie House. Years ago my youngest son and I put together a limited edition Lego set of the Robie House (which is actually still together in his room). I transgress a bit here but it is interesting the things that prompt people to want to go places / see things. I believe I mentioned in my Pittsburgh post that my youngest son really only wanted to that city to see Falling Water (due to us putting together the Lego set) and he also seems more inclined to go to places of other Lego Architecture sets we put together. The Lego Architecture series really is quite awesome and is eye-opening as there are quite a few buildings I had never heard of until seeing the sets (Robie House included). Anyway, back when we finished the Robie House Lego set I don't believe it was even open for tours but they have since cleaned it up and offer tours daily.   


Ok, back to the actual trip. The entire trip was clearly nostalgic for my dad as he had not been back to Chicago for over 20 years - he shared with us memories he had as a kid in the city, which included the Macy's store. Back when he was a child (this would have been early to mid-50s) it was a Marshall Field's department store. As we passed the display windows which had holiday scenes / settings he noted that they did the same thing when he was a kid and also noted that back then when you entered the store there was a huge tree in the middle area, which towered to the ceiling, and that the entire top floor had nothing but toys. The inside of the building is pretty stunning with the high roof and beautiful ceiling mural.



Ceiling of Macy's

We continued on to visit the Palmer House, which is a place my dad said was something he had always heard about as a kid as being a high-end hotel but never actual went into. Artistically, the inside was amazing. The surroundings made it feel like we were immersed in an oil painting, with beautiful decor and perfect lighting creating an air of awesome ambiance.





He headed to Millennium Park specifically to see the Cloud Gate (better known as "the bean").


The remainder of the evening was just strolling Michigan Avenue, which included going to Ghirardelli (which was right above the river).


The following day was more or less devoted to the Bears game. This was something which just happened to work out. We already made the travel arrangements when their schedule was released with them having a home game against the Lions. Although my dad has been a Bears fan for life this was his first visit to Soldier Field.


It was a bit surreal seeing a Bears game in person, knowing the history of the franchise and building. We happened to be there on a bobblehead day / were each given a Sid Luckman bobblehead...incidentally, he may have been the last great quarterback the Bears had. Seeing that he played back in the 1940's this is pretty sad.


The building breathed history and it seemed that all of the seats had decent views. That being said, it being such an old stadium made for some interesting traffic flow issues. For reasons beyond me we decided to go grab food during halftime (I blame this on my son). The situation was bonkers as people were jammed against each other making little to no headway as bulks were heading one way with the opposing force of bulks going the other way. This factor along with there being very few bathrooms with very long lines added to the awesomeness. What was even more fun was that once I entered the restroom there were separate lines leading up to each urinal (which of course didn't have partitions); so, as I'm sure you already guessed, once it was your turn there was someone right behind you as you tried to take care of business. I've never been able to go to the restroom with someone breathing down my neck...

As one can expect the lines for food were astronomically long. While my son waited in line for hot dogs and pretzels I went on search for any type of warm drink, seeing that it was about 30 degrees (not including wind chill). Of course, all that was offered in the stadium seemed to be cold beers and sodas...since we are all about cold drinks in freezing weather. On the plus side, I was able to find one food vendor which served a vegetarian impossible burger. Strangely, there was no line at this vendor...who would have guessed that the regular football viewing public isn't vegetarian...


So, back to our trip getting cut short. During the football game my dad received notice that their flight back to Portland the following day (which was around 8am) was cancelled. In checking the forecast, this was due to a massive snow storm which was set to hit around 11pm and continue on until mid morning the following day. It noted a chance of snow at 100%. Yes, 100%. Our flight back to Phoenix was closer to noon the following day and had not yet been noted as delayed or cancelled but the writing seemed to be on the wall. Southwest even seemed to know it was inevitable as they were allowing us to change the flight to a different day/time for free. Taking this into account, I found either an option of leaving that Sunday evening at around 10pm (which would beat the storm) or waiting until 4pm the following day, which would very likely have a delay or cancellation. Not wanting to mess with possible delays and snow storms I switched to the flight that Sunday evening. Due to such, we had to hurriedly pack after our return from the Bears game but luckily were still able to grab dinner with everyone before we headed to the airport. It is a good thing too as I was able to find this really cool French restaurant up the street from our hotel (Pierrot Gourmet at The Peninsula). The food and ambiance were great / definitely check it out if you like French food / themed places.


My final thoughts on Chicago is that I plan to go back some time in the near-future (possibly even next year) to hit up some of the museums and tours. And inevitably the Starbucks Reserve Roastery. I wonder if they just let people sleep there? The city as a whole reminded me of a less crazy New York / somewhere in between New York and downtown Seattle.


Next up : San Francisco

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