Solo Travel in Chicago`

My Solo Travel Experience in Chicago with Tips

For a person who hates to travel, how do I write for a platform which is designed for people who get an adrenaline rush by travelling? The first International Flight I took was in 2018, to U.S for an exchange programme to Indiana University, Bloomington and all I experienced could be described as anxiety and panic attacks.

To people who write “I love to travel” in their bio on dating apps, I am perceivably boring and vanilla! To those of you who have their plan laid out and are freakishly organized, I guess this read would just be a corny story of a single 28-year-old woman travelling solo in Chicago. But for those who share the same anxiety as me while travelling, this reading could just help you to open up your minds to take control or lose control while you are on the go. Let me share with you my plan and the outcome of my trip to Chicago for a week.

I was at Bloomington, Indiana University for a fall semester in 2018 and I thought of taking off to Chicago and travelling for a week. I took a shuttle to Chicago and enjoyed every bit of that ride! What’s not to enjoy? Pleasant weather, good bus ride, music on my pods and a good read “The Pig and the Skyscraper” by Mike Davis. I arrived at noon and took a cab to my airbnb near Forest Park, which I was looking forward to, because I had never stayed in one before. Unfortunately, the host was not available and I was on my own. It was evening by then and I thought about having a big meal, coming back, planning my next day and taking a rest.

Tip 1: Do your research. If you hate to travel, this is going to get you excited as well as prepared about what is going to come. While finding your airbnb keep in mind what experience you want on your trip. Read the reviews. They are important. I still cherish that I experienced one of the best homemade granola of my absentee host.

Now comes the planning part! When you sit to plan your travel, especially when you are travelling solo, hit a library prior to your visit and find a few travel books or even historical books on the city you want to explore. In case you are not a library type, a background and authentic website could also be of help. I had picked up a photo book and a book by Mike Davis. I made a list of things which I thought would be of interest in Chicago. For instance, I wanted to see the Field Museum, Millennium Park, Chicago River, North Michigan Avenue, Lincoln Park Zoo, Chicago History Museum. Locating these on a map was useful for me as it helped me figure out the Metra system.  On my list were not just museums and parks but also restaurants like Ann Sather’s, Millers Pub, shopping places etc.

Tip 2: Focus on things of your interest. It is not important to cover every touristy place in the city. Focus on experience rather than covering the points.

Day 1 started with enthusiasm to stick to the list and see most of the places and I succeeded at that. To be honest, this was to avoid decision-making fatigue. I started at around 9am and got to my airbnb at 10pm at night. I went to the Field Museum, took a water taxi, had lunch at Navy Pier, saw Willis Tower and went to Down Town and had dinner at The Berghoff Restaurant, which was the oldest German Restaurant, felt productive and happy, came home and slept like a baby.

Tip 3: I cannot emphasize this more, but commute with public transport as much as you can. Observe people, the subways, buses. And if you are confused, just ask someone, anyone on the streets!

Next day I planned to have breakfast at Ann Sathers’, which almost made me cry because the portion size of that cinnamon roll gave me a major sugar rush! It is not for weak-hearted and single people! I then went to Lincoln Park Zoo as planned and then went to the Chicago History Museum. Day 2 got me a little exhausted, not from travelling but from decision making and being organized all the time. I decided to cut myself some slack for Day 3 and go shopping on Michigan Avenue. I went to Sephora, treated myself a little and had a burger for lunch and went to Millennium Park. It was a touristy place with people all over the park clicking pictures. The Starbucks near to the park seemed more alluring to me. I went there and had a wonderful coffee and had dinner at Berghoff Restaurant.

Tip 4: Cut yourself some slack and break your rules and discipline. Explore your new sides. Having a cinnamon roll for breakfast was me breaking the rules.

I had initially planned to stay for 3 days in Chicago but I thought about extending my stay for 2 more days and was looking for another airbnb because mine was all booked for the next two days and hence my stay couldn’t be extended. I found an airbnb at a short notice in South Chicago. I was warned by my airbnb host and cab driver that the area was not good. I was apprehensive. I went anyway. I reached there and rang the apartment bell-a man in a tiger -print satin robe opened a door with a cigarette behind his ear and the entire house was smelling of incense with loud jazz music played on speakers. The man said “Hi Darling! You are adorable!” My fear went away because he seemed like a really nice man.

I put my stuff in my room and he had a friend over in the kitchen with whom he was talking and he offered me a cup of coffee on his kitchen counter. I felt invited and participated in the conversation. He was a real estate dealer and ran an airbnb. He asked me questions about India and I asked him questions about U.S education and why this neighborhood was being warned about. He told me the truth. He told me all about poverty, crime, drug dealing in the adjacent area which was largely inhabited by black people. He made sense! I read this all in Urban sociology and Urban planning and this man, who had never had a major in such disciplines, was making complete sense, because he had lived experience of theories of urban sociology.

I went outside after our good chat and went to Devon Avenue, which is a South Asian Neighbourhood in Chicago. I had Biryani from Ghareeb Nawaz. Being a South Asian, it was pretty obvious for me to explore that area and their market and I was amazed to see so many market places selling every South Asian thing from spices to grains in that market. People were looking at me as if they were trying to figure out if they have ever seen me or who I am? An Indian or Pakistani or Bangladeshi? I vibed with many of them while walking!

Tip 5: Always listen closely to what people have to say about the place, neighbourhood, experience, but go with your heart yet don’t do something stupid. Carry pepper spray!

The next day, which was my last day, my airbnb host offered to take me to the University of Chicago. I was ecstatic. He gave me a ride and he took me to all places to explain gentrification, showed me project housing, gave me an experience of taking away the heavy meaty burger and sugary creamy coffee from Mc Donalds. He took me to show a few houses in the black neighborhoods in which he deals in real estate and explained about property prices, mortgages, foreclosures and gentrification to me. None of my teachers or even a book ever made that sense! By the end of our mini-trip, he took me to a shop where Afghanistanis sold Newport at a cheaper rate and who were boggled to see a new face with him, thinking I may complain to authorities. We then came back and he cooked pasta for me and we watched a movie, thanked him for the day, slept, and left with a hearty goodbye the next day.

Tip 6: If you find a friendly and welcoming person and are apprehensive about them, then just take all the safety measures like sharing your location, contacting your close friends/family. If they have good intentions, I am sure your fear will fade away in time and you will be lucky to have a friend!

You see what I did here. I have given you two experiences. One was that of a planned trip where exploring the city is largely an outcome of your curiosity to see tangible things, experience the city through walking and observing people, while the second experience was about letting go and opening your minds to what may come. Experiencing the city through people and communities who had a central place in making the history of the city. Each way is a good way as long as you return with a happy heart to your home. For me, trusting in people while travelling turned out to be a good thing. I met new people in streets, restaurants, parks, zoos, we shared our stories and parted ways knowing that there is always goodness in travelling and there is more than one way of travelling! This may not always be the case. Hence, one needs to maintain a balance between being free-spirited and careful. So, next time someone tells you that you are not sportive for travelling, tell them that you have yet to explore your way of travelling! Yet I would suggest keeping a basic level of organization when travelling solo, because I am yet to share my experience when I lost my passport in Chicago while travelling back to India. That’s for another day.


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