Packing for Adventure

Chicago is a great place to spend a day or two! Remember that the whole purpose of this trip was to try the best pizzas in the country, so tourism was a lesser priority. Even so, we really enjoyed our time there!

Where We Stayed:

With such a limited amount of time, we prioritized convenience over luxury when it comes to sleeping. We stayed at the Best Western near the O’Hare Airport. No complaints!

Getting Around:

As for inner city travel, we opted for a rental car. The factors that led to this decision were money, convenience, and safety. Our other choices were using Uber or the “L” Train (elevated subway).

• Money– with all the stops we were planning to make, using Ubers would start to add up, making a rental car or Ubers about the same. The “L” Train would have been our cheapest option at $2.50 per ride.
• Convenience– it doesn’t get much more convenient than driving yourself around! Even picking up/dropping off the car at the airport was pretty slick. Ubers are also pretty convenient, but it involves less independence. As for the “L” Train, navigating a new subway system in other cities can be intimidating. We didn’t want to get lost or waste too much of our already limited time figuring it out.
• Safety– driving ourselves around seemed to be the safest choice. I’m sure we would have been fine using public transportation, but we’re from a small town and didn’t want to worry.

We were worried about difficulty finding parking, but we didn’t have any trouble. Maybe we got lucky.

Sight-Seeing:

Willis Tower Skydeck + The Ledge

Our first stop after eating lunch was the Willis Tower (formerly known as the Sears Tower). We had booked tickets to the Skydeck and the Ledge ahead of time, so we had timed tickets. We did not pay for an expedited entry, but the wait was not bad. We went up and walked around and enjoyed the view of the city and then got in line for the Ledge: plexiglass extending out of the building you can stand on to feel like you are in the air. Pretty nerve wracking, especially for the nation’s 3rd tallest building! But it was fun, and we got some cool pictures.

Even without the Ledge experience, the building felt like it was swaying, which is definitely an unsettling feeling. Maybe don’t take anyone afraid of heights.

Chicago Federal Reserve Fed Money Museum

As a banker, I was excited to see the Chicago Federal Reserve Building. I have a coworker who had been to the building for a training a few years prior, and he said it was a really cool building. So I was disappointed to find out they do not allow tours. They do, however, have a free Fed Money Museum. It was pretty small, but interesting enough. Swing by if you’re in the area.

Architecture in the Financial District:

Chicago also has some pretty neat architecture. Just walking around the financial district is pretty cool. All the places we visited were within walking distance of each other.

The Rookery: It has a lovely interior and some pretty cool stairs (but you are not allowed to climb them).

The Old Post Office: I was excited to see this. Reviews make it sound like it’s really amazing, so I think I was expecting it to be more than it was. The exterior looks like… wait for it…. An old post office. The inside is completely different and very modern. It’s a really nice space, and we sat and just kinda tried to take in our surroundings. Special events can be held there, and that’s exactly what it would be great for. People also take their laptop to work from home away from home.

Missed Opportunities:

My native Chicagoan colleague had said to come on St. Patrick’s Day (our anniversary is mid-March). They have a parade and dye the river green. I tried really hard to make it work, but it would have put us there on a weekend and the flights would have been more expensive and it just would have thrown off the whole trip. I’m sure it’s a lot of fun!

The other thing I was bummed to miss was the Art Institute of Chicago. Any Ferris Bueller fans out there know the painting I’m talking about: I really wanted to see “A Sunday Afternoon on the Island of La Grande Jatte” by Georges Seurat, but the museum is not open on Tuesdays. I tried really hard to make it work! But I ran into the same problems I did for the green river. Plus this trip was a gift to Chris and he would have hated it.

Spoiler alert: I came back about seven months later on a work trip by myself and got to see it without worrying about Chris being bored.

And just like that, our day in Chicago was over! We packed a LOT into a half day and we were excited to continue our Pizza Crawl! Stay tuned for Detroit!

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