There’s cities you hear about all your life for various reasons. Paris, London, Rome, Beijing, Manila, Rio de Janeiro, Calcutta, Cairo… all places I thought about and imagined going to. When I think of the US, New York City, Los Angeles, and Chicago pop up first. I’ve technically been to the 2 former… Chicago wasn’t necessarily in the MUST-SEE plans. I still see it as more of a business center than a tourist destination. Alas, one fateful day a few months ago I got a call from my brother asking if I’d be interested in going with him to the Windy City to pick up a transmission for his car. Round trip, I drove over 4k miles!
Atlanta -> Dallas -> Chicago -> Dallas -> Atlanta
which actually was more like…
ATL – (overnight) Pearl, MS – Dallas – (overnight) Springfield, MO – St. Louis – Chicago – (overnight) Tulsa – Dallas – Vicksburg, MS – ATL
WELL, I’m certainly never one to pass up the opportunity to learn a new city. Although a part of me sort of hoped he’d call and cancel before I left, I made a deal that we had to stay long enough for me to get some good info to share with you guys! So, here I am, ready to give you the DEETS.
I feel I must preface this with the fact that this is NOT a budget friendly city. As a thrifty traveler, I had no idea what I was up against… and that’s not the first time. However, I view everything as a learning experience, I learned so you will know. I still did my best to do free things in a city that is full of expense. Let’s begin!
The first thing you should prepare for is spending that paper on parking. I stayed at a Marriott downtown and got a rude awakening when I saw $60 parking for the night. In my disbelief, I kept driving around. I was sure, at least had hope, that the heavy fee was due to being a hotel. How wrong I was. Parking was by far the biggest expense in the whole trip. $60 was the cheapest, actually. If you’ve been around for a while you know I don’t rent cars and usually just walk a ton or take the train. It would have been cheaper to park outside the city and take public transport in. I actually paid less for the hotel room than I did for parking. To be fair, I did get a discount on the room but let’s just say the 2nd night in Chicago I stayed in the suburbs. To make it easier, there are apps that you can reserve spots at and pay in advance so you won’t have to drive around but if there’s anything you want to make sure there’s budget for, it’s parking.
One thing I loved about the city is how it’s so very different than any other city I’ve been to. I mentioned I’ve been to NYC, not as a tourist though, really just passing through so I don’t have endless skyscraper experience that I should have but I think NYC is the only city that could work to compare with. From the little I did see of NYC, it really brought to life the term concrete jungle for me. Just and endless sea of towering gray buildings that make it look sort of futuristic and cramped at the same time. That was Chicago. Like Paris, I’ve seen Chicago in movies and photos for as long as I could remember. I thought I understood what it looked like. In the words of Game of Thrones, “You know nothing, Jon Snow.” I am Jon Snow. So. Many. Skyscrapers. So many buildings. I am so often in nature it’s oddly refreshing to be in such a bustling, famous, and full-of-tall-buildings city. There are several you can tour and get photos in, such as Skydeck Chicago. If you have a friend who has been to the capital of Illinois, they likely have posted a photo of them where it looks like they are standing on air with this spectacular view behind them. I wanted to do that but someone I was with *cough* has a fear of heights. Maybe next time!
Cloud Gate (Chicago Bean)
Even more popular than the Skydeck photos are the ones in front of the BEAN… or Cloud Gate. This is super touristy so don’t expect to have a moment where it’s just you and the silver monument alone…. unless you have the discipline to get up ungodly early. If so, kudos. You can drive by and see it but you have to find parking to get to it and that’s a little bit of a drive (because 1 paragraph about the horrors isn’t enough). I will say that the lot is this massive underground place where you can escape the cold and effectively get lost. Another great example of not knowing and suffering the consequences. On a positive note, if you can navigate, 1 of the many parking lot exits can take you to the corner of Millennium Park that you walk through to get to Cloud Gate. My brother and I did get lost on our way back to the car because it’s 100% the biggest parking lot I’ve ever seen. Being underground didn’t help and we walked in circles… even though I took a photo of where we got out at.
I have to tell a hopefully quick story here! While I was admiring and getting photos in the cold and waiting for my brother to reappear, this college aged male and female came up and said they were doing a research study for class and wanted to ask me a few questions. Sure, I’m always happy to help out. I should have known something was wrong when the dude was wearing open toed shoes in freezing temperatures. haha Anyway, they were asking my feelings on happiness and how I hope to feel about love vs happiness at end of life etc. I’m naive enough to think I’m still helping. The story eventually took a turn and they wanted to talk to me about Jesus Christ and how their beliefs were different than mine and how to get me to their side. Luckily, my brother rescued me but definitely 50 shades of awkward. No thanks.
I really wish we had of had more time because Lake Michigan sort of hugs Chicago and it’s such an interesting contrast of landscape to look at. The best place to take it in is at Navy Pier. When you’re at the tip of the pier, you look out into the vast lake and see water for days. Turn around, you see BUILDINGS for days. Between the tip of the pier and the chaos of the city, you have this slice of nice that makes up activities of the pier. My favorite thing was the litany of restaurants in a walking stretch looking out at the water. Just when you thought you’d walked by a dozen food stops, you continue to walk by a dozen more. SO MANY FOOD SOURCES! Conveniently parallel to loads of (pricey) parking. Luckily here you can pay by the hour and not the day so no need to worry not getting use of the space. The fun thing about the pier, aside from the panoramic view, is there’s always events going on. If I lived in Chicago, I’m pretty confident that would be my hangout.
My 1 food goal was to eat Chicago Deep Dish in Chicago. After reaching out to you guys, I got so many pizza recommendations! Thanks for input! The one name I saw the most was Gino’s. So, that’s exactly where we went and boy, was it worth it. Thank goodness calories don’t count on vacation!
I would love to go back 1 year for St. Patrick’s Day where they dye the Chicago River green! To be honest, it might be too cold though. It got shivering cold at night, in the low 40s. For the first week of May, being from the south, I’m used to 90s and in fact, it was in the mid 90s when I left Texas to head north to Chicago so it was a rude awakening! I’d definitely like to try the city in the summer, enjoy the lake and parks with pizza. Have you been to Chicago? Feel free to share tips with me on what I should see next time! If not, follow me on Instagram or Facebook where I’ll discuss more in depth about each location with fun facts.