Exploring Chicago

The kids had one week all summer where they didn’t have some sort of activity planned.  Unfortunately, things at work were pretty fluid with travel and meetings, so I was hesitant to make any major plans.  However, about a week before the kids were free I finally decided that we needed to take some time off, so we started talking about destinations.  I was thinking some place close and the kids thought that Chicago sounded like a great idea.  Liam wanted to go to a Cubs game and Ann wanted to go to the theater.  With those goals in mind we started to see what sort of reservations we could land so close to the events.

The first question was if we should drive or take the train, or a mixture of both.  I thought that the train was the best option as we wouldn’t have to deal with traffic and parking.  Plus the train had benefits like bathrooms and the ability to walk around.  The downside was we would want a more expensive hotel downtown preferably close to public transportation.  In the end the train won out even though it left at 7 AM.

Getting a hotel was not too difficult.  There are plenty of rooms in Chicago so even though several locations were sold out, we still had a number to choose from.  Finding a decent price and a place with a pool, (something Liam really enjoys), was another thing.  We ended up booking a room at the Embassy Suites a block away from a subway station and within easy walking distance to things the kids wanted to go to namely the Miracle Mile and the Navy Pier.  It not only had a pool, but an included cook-to-order breakfast.

The next question was what sort of show was in town that both kids would enjoy and was appropriate.  The Broadway show currently playing was Book of Mormon, so that was out.  The smaller venues had a couple things that Ann thought looked interesting, but would probably drive Liam crazy.  We finally found a small yet professional production of Little Shop of Horrors with plenty of reasonably-priced seats, so stashed that as our theater pick.

The final hurdle was trying to get tickets to a Cubs home game.  They had a couple that week and although tickets through the official means were long-gone, I tried the resale market.  Liam first wanted bleacher seats, but then decided that something in the outfield along the third base line was more desirable.  One of his goals was to catch a ball and this area statistically had the most foul balls hit its way.

At first we were looking at a Wednesday afternoon game and I found some tickets, but only in a set of four.  They were also expensive–especially so as I would have to buy an extra ticket and figure out something to do with it.  We then looked at a Tuesday evening game.  I was a little apprehensive at this idea since we were leaving early Tuesday morning and I thought that it would be a really long day.  But the kids decided that they were more excited about a night game so we restarted the ticket hunt.  It must have been meant to be as we found a set of three tickets in the fourth row right in front of the bullpen which actually cost less per ticket than others I almost bought about 20 rows back.

With the main purchases out of the way—train, baseball and show tickets plus a hotel reservation—we were set to go.  The rest we would figure out on the way.

Day 0

As we were packing Ann decided that she had nothing to wear and threw a heap of clothes into the giveaway pile.  We went out to do some quick shopping after lunch with the idea of getting back around dinner time and finishing packing.  After about seven hours and countless stores Ann had only found one jumper to buy.  Since stores were now all closed we headed back home and Ann managed to find enough clothes to pack.

Day 1

We agreed to leave at 6 AM in order to give us time to get to the train station and park.  Ann as usual was running late so we ended up leaving at 6:15. The GPS still had us arriving 15 minutes before the train left, but then we ran into some rush hour traffic.  We finally arrived five minutes before the train was due to depart…and I had no idea where I could park as the lot in front of the station only had two-hour meters and the streets around the station only allowed parking during certain hours of the day without a resident sticker.  I dropped the kids and luggage off and told them to get in line while I ran in and asked the nice gentleman at the ticket window where I could stash my car for a few days.

As it turned out, there was a free lot across the train tracks and the train was running late.  I quickly drove across the bridge over the railroad tracks, secured a spot then jogged up the stairs to cross the tracks again before descending to the platform to find the kids standing in line engrossed in their devices.  The train ended up being about 20 minutes late due to construction, so the rush was unwarranted.

At first finding a set of seats next to each other seemed to be an unlikely event.  But after turning around and heading all the way to the other end of the train we found several free seats.  The kids sat next to each other and I was across the aisle from them.  After a little bit of traveling we decided to try the dining car.  They did not have any breakfast sandwiches left by then so I bought a chicken wrap and fruit, Ann picked a container of doughnut holes and Liam decided to try the Angus burger.   While it was just a microwave burger, Liam loved it and couldn’t wait for the train ride home to get another one.  After breakfast, Ann slept for a good portion of the ride while Liam and I watched a movie and played some cards.

I had done a little research into the mass transit options in Chicago.  I figured that we would ride the ‘L’ most of the time to get around along with busses where needed, (there was an ‘L’ stop a block away from our hotel which is one reason I picked it).  The kids and I wanted to try Uber, so planned to do that to and from the theater since it wasn’t near an ‘L’ station.  But my plan for today was to get each of us a three-day transit pass at Union Station and hop a ride to our hotel.  I had assumed that there would be an ‘L’ stop inside the train station, but as we were about to purchase our passes an attendant told us that the closest “Red Line” stop was a ¾ mile walk and our best bet was to take a bus.  He also said it was more cost efficient to purchase a single Ventra card and share it.  Since I didn’t want to try and figure out options we decided to just take a taxi. Even though it was still morning, we were able to check into our room.

(The rest of this journal entry has unfortunately been lost.)

2023 Update: While I do not know what happened to the rest of this journal entry, I do remember some of the highlights of the trip. We had a lot of fun riding the train as well as using the (new to me) Uber app. Although, after exiting the theater after seeing “Little Shop of Horrors”, we found ourselves in a torrential downpour. That is when I discovered that Uber changed their rates during periods of demand, and that obviously many people were hiring rides instead of walking. We explored several shops that were in spaces that did not seem to be designed for shops with small maze-like rooms spanning multiple floors. One evening we walked around the Navy Pier capping the night with a fireworks display that we watched along with several boats anchored haphazardly on the water. I introduced the kids to deep dish pizza and we all experienced a Chicago-style hot dog at Portillo’s. There were wild jet boat rides and calmer boat tours, lots of walking through parks and along city streets, and browsing interesting shops including the largest candy store I had ever seen. But the, or at least one of the top headline moments was the Cubs game. One of the pitchers who was warming up on the field right in front of us threw Liam his ball when he was done.

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top