Ky Takes Chicago Part II

Day two in Chicago started out in a bit of a frenzy. The person I was traveling with decided to head back home so now I was a solo traveler in Chicago. After I got over the initial fear of being alone, I found freedom in the whole situation. I moved out of the Airbnb apartment and found lodging closer to all the action. I was in the center of the Magnificent Mile. Luckily Jack, my Airbnb host, was nice enough to drive me to my new hotel. Once I checked in to the Inn of Chicago, I decided to walk along Michigan Avenue to explore.
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Almost immediately I came across Lake Michigan on the DuSable Bridge. I walked downstairs to see if I could get in on the boat action happening on the lake. I noticed there were a few boat tours and I figured taking one would be a great way to learn more about the city. All of the tours were sold out until 5:30PM which meant I had 3-hours of free time.

Magnificent Mile

I headed straight to the Bean in Millennium Park. It was actually pretty cool. The bean is made out of silver steel so it’s like a mirror of some sort—it reflects the city skyline as well. People gather from all over the world just to touch it and get a picture with it. I even found myself envious that I wouldn’t get the picture I wanted so I decided to take selfies until two nice ladies took my full-length pic for me (the struggles we have nowadays…millennials).

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From The Bean, I headed across the street to the Chicago Cultural Center. I stayed in there for hours exploring the exhibits. The architecture was beautiful. There was one specific exhibit that I loved called Love is for Sale: The Graphic Art of Valmor Products. What I loved about this exhibit is it raised awareness about the conversation of beauty in advertisements when catered to black women (and some men) back in the day. The ads promoted bleaching creams, wigs, and attaining “good hair” with Valmor Products. I’m always amazed by the ads of our dark past. Some of them were offensive and would make me feel inadequate as a black person (if I lived during those times).

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My tour of Chicago via Lake Michigan was the perfect way to get more acquainted with the city. I learned about the architecture, took in the beautiful views and just enjoyed the amazing weather. If you’re ever in Chicago, you have to take one of these tours on Lake Michigan.

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My day wouldn’t have been complete without a Deep Dish Pizza for dinner. I waited in Giordano’s for an hour before my pizza was ready. It was a total of $24 but so worth it. I was so exhausted by my day that I decided to take my deep dish back to the hotel. Let me just say this, deep-dish pizza is the best food creation on the face of this earth.

Giordano's Deep Dish Pizza Chicago

My First Experience as a Solo Traveler

Alone. Not by choice. My boyfriend (at the time, we are no longer together) and I got into an argument. We parted ways that weekend. I was on my own in a huge city much like my own, but it was not NYC, it was different and I would be doing a disservice to Chicago if I compared the two.

Alone. I never anticipated Chicago being a trip for one but God always has other plans for us, doesn’t he? After settling in my new hotel, I decided to wear my hair in its natural state to represent the sudden burst of freedom I now felt. It was liberating to say the least. The first thing I did was explore the Magnificent Mile. I walked outside of my hotel, conveniently placed on the corner of Ohio and Mag Mile and proceeded down the strip admiring the tall buildings and the shopping. I was in Chicago for sure. There were stores for days—Louis Vuitton, Chanel, Guess, Ralph Lauren, Under Armour, Neiman Marcus, H&M and the list goes on. I decided to take a boat tour of Chicago along Lake Michigan followed by a trip to “The Bean.” I looked around at all the people swarming towards the bean with their families and friends and at that moment I wished I could share this time with someone—but I couldn’t so I did what anyone else in my situation would do…I found someone who had a nice and friendly demeanor and asked if they could take a picture of me—I was alone in Chicago, but that didn’t take away from the fact that I was still a tourist. I met two middle-aged women who were more than happy to take my picture. They complimented me on my natural hair, in awe of what I did to make it look the way it did and went on about their day. I felt exhilarated. My fear of being alone in Chicago wasn’t completely gone, but I loosened up. I would make the best of this trip and enjoy the wonders of solo travel.

The next morning, I woke up and had time to reflect. I sat in silence. I prayed. I talked to God. I was able to write. I planned out my itinerary. I talked on the phone. I did everything I wanted to do in MY time. I planned to do a museum day. I would visit all the museums in Chicago that were on my itinerary. Three museums in one day. As a matter of fact, three museums in five hours, since I didn’t get to my first museum (The Art Institute of Chicago) until noon and everything closed at 5PM. I say this all to say, I was on my own time. I didn’t have to answer to anyone else but me. I was accountable for how my trip would go. This was the day that my fear of being solo in Chicago completely left me. I no longer feared someone would notice I was alone, or that I would be kidnapped. I let go of everything and lived life. I enjoyed my time walking through the exhibits of the Art Institute, interpreting art from my perspective and not the perspectives of others. I enjoyed taking pictures of pictures at the Museum of Contemporary Photography and watching the Dandy Lion video over and over again without being rushed by someone else. I loved learning about the history of African Americans at the DuSable Museum and getting caught in the rain, looking for the bus on the way back to the hotel. It was beautiful. It was liberating. It was such a necessary experience to push me out of my element. That night, I decided to take myself to a nice dinner. I wanted to visit the Wild Hare with my ex. boyfriend and dance the night away to reggae music, but things did not turn out as such—so guess what, I visited without him. I arrived at the dinner around 7:30PM and I was surrounded by other couples on date night but that didn’t faze me. I asked the hostess for a table for one and ordered my jerk chicken plate filled with cabbage and rice and peas. I had an ice-cold drink to go with my dinner and danced for a few hours to old school reggae music. When it was getting late, I took a cab home and got back to my hotel around 11PM. The next morning I took the CTA Blue Line train and found my way back to the airport. Overall, it was such a beautiful trip.

My first time as a solo traveler was an experience. I am not going to act like it wasn’t scary because it was. I don’t like being alone, especially in a hotel room by myself but now, I understand that this time alone was exactly what I needed. I had time just to spend with myself. I had time to think and evaluate my life decisions. I was surprised by my own strength because I could’ve just remained in the room, stagnant since I was alone, but instead, I was empowered. I got up and did everything that was on my itinerary. I am now more open to an experience like this.

Ky Tip: 10 Tips to Conquer Solo Travel as a Woman

  1. Be Bold: Do not be afraid of conquering the city you are visiting. Make sure you know everything you want to get done and go for it.
  2. Prepare: Before I started each day, I had an idea of the things I wanted to do and how I would do it. I also googled what time everything opened and closed, and planned my daily itinerary based on my research.
  3. Don’t be afraid to ask questions, directions or someone to take a picture of you: Just make sure who you ask makes you feel comfortable.
  4. Try to get home at a decent time: I wouldn’t advise staying out until the wee hours of the night especially as a woman traveler. Safety First!
  5. Treat this new city like it’s your own and you deserve to be there: My friend gave me the advice to act like I was out and about in NYC and once she said that, my whole mindset about the trip changed. I wouldn’t be so cautious in NYC so why should I be afraid in Chicago?
  6. Enjoy time with you: Take time to breathe, read or even sit in silence when you’re on your solo trip.
  7. Don’t be embarrassed to have breakfast, lunch, or dinner by yourself: Again be confident. You may get stares, which is expected, but people will ultimately respect your independence. However, it’s okay if you just want to take your food back to the hotel. #NoPressure.
  8. Meet Up: If you’re going to a new city solo, see if your friends or family know of anyone you can connect with or if there are any events or meet up groups happening.
  9. Treat Yourself: Maybe it’s a cupcake or a new outfit but make yourself feel special…you deserve it.
  10. Little White Lie: Never tell someone you are alone. Safety First!

Chicago Travelbyky

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