I’m an all or nothing kind of girl and one could say I was all in for this Chicago trip. Mainly because it involved my best friend, donuts and Beyonce. I mean…three of my all time favorite things in the entire world. It was such a last minute trip that there was very minimal planning involved and even less sleep. And when I say minimal planning I mean it. I woke up at 4am the morning of my trip and I wasn’t sure if I was flying into O’Hare or Midway, I had no idea which train to jump on when I landed and I definitely didn’t know which direction to walk when I got off the train…more on that later (little details I tell you). I fly by the seat of my pants for things like this and what would give most people a mild heart attack is my cup of tea. I had no plans other than trying to become a regular at the Dunkin’ Donuts in the two days I was there and being in the presence of the queen bee. Other than that, I had about 36 hours to kill by myself in a city I’d never explored. Before you can fully understand the excitement and hilarity involved in this, you should know how extremely directionally challenged I am. I’m the type of person that approaches a one way and somehow goes the wrong way.
The night before I left, I worked on a few custom illustration deadlines until 12:30am and I got a solid 3 and a 1/2 hours of sleep before jumping on the plane. When you only have 36 hours in a city, you must use that time wisely and I did just that by proceeding to stay up for the next 24 hours. I’m still recovering…not my best move but there is no sleeping after being in the presence of Bey. Thankfully there is some sort of coffee shop on every corner and to my delight, a donut shop as well. I’m not sure why the rest of the country hasn’t caught on to this genius idea but it was definitely a glimpse of heaven to me. I would highly recommend Do Rite donuts on Randolph and Dearborn. I’ve had a lot of donuts and their Old Fashion Apple Cinnamon donut is hands down the best I’ve ever had. So good that I was determined to bring some back to my people in Minneapolis. That was a great idea until I got hungry on the plane home…fail. You just can’t leave this girl with a bag of donuts.
After I had my second venti of the day at 9 am (this is impressive to me), I was ready to explore the city. My main concern was getting so lost that I couldn’t eventually find my way back. It was easier than I thought it was going to be. I mainly stayed in a square surrounding Ali’s apartment and kept in mind landmarks that I would recognize if I got off track. My first mistake was picking the Starbucks and Dunkin’ Donuts as the landmarks near her apartment. Big time LOL when I took my first walk around the city and I could have sworn I was near her apartment until I realized there is literally a Starbuck and Dunkin’ donuts everywhere you turn. The only map I had was on my phone and I really don’t understand those things when I’m on foot anyway so it was useless.
All jokes aside, my number one piece of advice when exploring a new city is venture out by yourself and leave your map at home, it’s the only way to truly discover the gems of a new place. My second piece of advice is talk to people while you’re there. My secret weapon was the doorman. He knew the city like the back of his hand and he knew which method of transportation was best to get there. If you’re looking for good places to go and you don’t want to break the bank, ask college students…they will know the best, cheapest spots in town. Or if all else fails, go where it’s busy, it means it’s good. I had no problem finding the best places in the area because I was staying with my best friend who is lucky enough to live there. She happened to direct me to all of the spots that Beyonce stopped while she was there. Somehow I just missed her every time (sigh).
Okay so here is my list of how to do Chi in 36 hours.
1// Fly Spirit airlines. I got my flight for $120 roundtrip from Minneapolis to Chicago. Their flights are typically delayed and you have to pay quite the price to bring a carry on. I packed everything into an oversized purse that I needed. I wore my outfit on the plane for the first day and packed my concert outfit and bought part of the second outfit while shopping.
2// If you need recommendations of what to do while you’re there, ask your Facebook friends in a status. This way you will have some sort of idea of what to do while you’re there before arriving and you don’t have to do a ton of research.
3// Walk down Michigan Ave. Stop into Zara and Topshop. Dream about being able to shop at the 5 story Burberry (look but don’t touch). And then remind yourself that you’re a broke artist and keep walking…wait that’s just my strategy.
4// Go to Millennium Park. You’ll bump into the bean and fountains. (great for kids) An overall tourist spot. You just might be lucky enough to catch a symphony playing in the park like I was.
5// Get the Chicago mix at Garrett’s Popcorn on Randolph and Dearborn. It’s ahhhhmmmmmmazing.
6// If you’re into this sort of thing, go to the Art Institute and visit the modern wing. I only had time to stop in for an hour but it is a beautiful collection that I am so glad I had the opportunity to see.
7// Go on the architectural boat tour. I didn’t have the opportunity to do this because I ran out of time but I watched people on boats and buses experiencing this and it is definitely on my list when I go back.
8// Go to Beyonce.
9// Look up. My overall experience of Chicago on this trip is how beautiful a busy city can be. Usually I’m turned off to the bustling and business of a big city because most days I prefer the pace of the country over the city life but this trip was different. I had no agenda and I spent most of my trip capturing the beauty of the city as I saw it. I constantly was looking up at the contrasting buildings and I was astonished at how nature nuzzled its way into the city. Chicago completely took a piece of my heart and opened up a new perspective for me. Now all I want to do is wander to new places, leave a piece of me there and take some of it with me. For now I will be in Minneapolis dreaming about my next adventure and working until my wandering heart finds a new place to go. Thank you for such a new perspective Chicago.
*All pictures were taken with my iPhone and edited in after light or on the iPhone photo editor.
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I’m Katie, the brand strategist, designer, dreamer, and entrepreneur behind Artful Brands. Dreamy typefaces, clean layouts, and soft color palettes are my love language— but more importantly designing strategic brands that book.
Sound like a perfect trip. Cheers to you!