My First Experience as a Solo Traveler

Alone. Not by choice. My boyfriend (at the time) 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 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, 3-museums in 5-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 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 to 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.

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 for 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 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 here?
  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’s 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

11 Replies to “My First Experience as a Solo Traveler”

  1. Wait, so you broke up while on vacation? Damn that sucks. Well good job keeping your head up and exploring such an outstanding city. Great tips.

  2. So great to meet u Ky! I am also a travel blogger! I did my first solo trip in 2011 and it was life changing. Even now that I am engaged I like to have time to myself to recoup and get my mind straight. You have great tips. I hope you try it again! I love road trips and beach vacas as well for female solo travel.

    1. Hey Gurl!!! Really, in that case I have to try it again! I must admit I was scared at first, but once I got in the groove of things it was fine. How do you combat the initial jitters?

  3. That is really cool ! I am myself planning to go on one . Your article gave me confidence to turn my dream into reality soon 🙂

  4. Good for you! Solo travel is life changing, you learn so much about yourself. I definitely agree with your tips. Cheers to a new chapter and happy travels!

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