Guide to Traveling Chicago Solo

Chicago. Chi-town. The windy city. There’s no wonder why it’s referred to as the “Jewel of the Midwest”. The shiny and reflective structures, mind-blowing architecture and sophisticated museums make it one of the best cities to visit in the U.S.

I arrived at Chicago O’Hare completely on my own, as I had a conference for the American Association of Suicidology there. My biggest blunder was booking my flight way in advance without realizing I would be spending Easter there—meaning I would be completely alone and almost everything would be closed very early. Nevertheless, I used that extra time to finish up some school work since I knew I would be arriving about an hour before class started. I also did some research on where I should visit first and what to put on my priority list. Here are some things that I was able to see:

University of Chicago

I didn’t originally plan on visiting but the university is right next to Frank Lloyd Wright’s famous Robie House. The wait was about an hour, so it gave me enough time to explore the university. I try to explore as many universities as I can so that I can see what campus life is like around the world. Since my boyfriend is going to be a future architect, his passion has definitely influenced me to want to see more art and famous buildings around the world. The school reminded me of what an Ivy League school would look like—castlelike structures, old chapels, and strands of ivy draping over every side of the buildings. They also had two beautiful libraries that I could not wait to get a glimpse of. One of the libraries reminded me of something you would find in Hogwarts—spacious and incredibly ancient and prestigious. The other library was extremely modern, much so that I did not know it was a library until I looked further within the structure. It was entirely made out of glass and you could see students working and reading. It was not open to visitors but I was glad I got the chance to see the exterior in person. My favorite campus surprise was the food trucks. I ended up going to the truck with the most people in line (usually means it’s the best) and I had a spicy kimchi taco which was delicious and extremely affordable. Overall, it was a great way to kill time and see some new things.

Robie House

This is a house that has a lot of history and is now part of the University of Chicago in order to keep it preserved. It is actually one of the first “modern” homes and inspired so many other similar styles that are still used in homes today. When you go in, they will tell you that you cannot take pictures unless you pay for a photo pass. Play dumb. Don’t waste your money on this and wait until your guide turns around or the group leaves so that you can take as many pictures as you want. They are just trying to get more money out of you, which isn’t right.

The Bean (Cloud Gate)

Nothing is more iconic than the famous Chicago Bean. This structure allows you to get amazing pictures of yourself and the Chicago skyline. The whole point is for you to interact with the sculpture and create something unique.If you go underneath, it becomes even more abstract. You can lie down and take pictures or take a video around the bottom perimeter to get some cool views.

Millenium Park

This park was absolutely perfect for taking a leisurely walk or a morning run. I would come here to eat breakfast (a healthy one consisting of donuts and hot chocolate) and stare at the magnificent views of the city and of the Bean.

There’s even a gorgeous silver bridge that takes you from one side of the park to the other.

This amphitheater is perfect for performances and springtime picnics. They would also show free movies here and have events so the public can gather together. It’s literally a small town feel in a big city.

Let’s get to the most important part…

THE FOOD

You obviously can’t leave Chicago without trying the deep dish pizza or Garrett’s Chicago style popcorn.

Garrett’s popcorn: Chicago Mix- cheddar cheese and caramel. Sounds very strange but it goes together better than peanut butter and jelly. Trust me.

Lou Malnati’s: Giordiano’s is also a very famous contender here but they do not offer personal pizzas. I prefer a smaller, thinner crust so this pizza was absolutely perfect for me. There’s a bit of a wait but it’s totally worth it.

Donuts: Stan’s, Firecakes, and the Donut Vault are some of the most famous donuts in the Chicago area. I personally only tried the last two and I preferred Firecakes for the funky flavors. The presentation is also gorgeous making them pretty much Pinterest famous.

The Girl and the Goat: This is one of the most highly rated restaurants in Chicago. Although I did not get a chance to go here due to my limited budget, it is highly recommended and I will go there when I visit again.

Beatrix: Very upscale yet affordable and great service. I met up with a friend here and the waiter even gave us a free drink since he saw me looking at her engagement ring and thought we should celebrate. The food and dessert were both delicious. I got the salmon with mole sauce and the chocolate cake.

Where to Stay

I stayed in a quaint Airbnb apartment which was really affordable, but I wish I would have realized that anyone could rent out the other private rooms. That made things a little uncomfortable but I was completely safe and had a lock on my own door. I stayed near the University of Illinois at Chicago and it was super close to the train station which made traveling a lot easier.

Transportation

I went back and forth from using the train, Uber, and cabs. Once I was downtown, Uber was extremely cheap and efficient for getting to all of the sights I wanted to see quickly. I also did Uber Pool which made rides even cheaper (about $5-7).

Sights

Get the Chicago GO Pass and you are free to see many popular sights such as the John Hancock Observatory, the Willis Tower and skydeck, as well as many museums. You can’t miss the Art Institute of Chicago, which houses many famous paintings and is where Ferris Beuller and his friends share a deep moment looking at the art. The pass also included a beautiful architecture cruise along the Chicago River, where I learned about the history of the architectural boom after the Great Chicago Fire. Who knew that fire could pass through a river?

The Art Institute. The Chicago GO pass got me to the front of this line.

Walk over the city on the glass SkyDeck

Tilt over the skyline at the John Hancock Observatory (P.S. Don’t buy the photos. Just pretend to talk to the lady and take the pictures on your phone since the screen is at hip-level. It already costs extra to do the tilt so might as well get more out of it.)

Where to Shop

Magnificent Mile- The Rodeo Drive/5th Avenue/Grafton Street/Oxford Street/Worth Avenue/Bal Harbour/Ginza of Chicago. This was the only area I walked alone at night.

If you have more questions about visiting Chicago, feel free to leave a comment below and I will get back to you as soon as possible! I was only here for a week but I was able to get a lot done considering a lot of my time was also spent at a conference.