How To Experience Chicago

Last weekend I took advantage of the opportunity I had to go to Chicago alone. This may seem like a scary experience for some people, but as long as you do it right, it’s actually a rewarding one. By being by myself, I was able to really take in every thing the city has to offer and appreciate its natural beauty. If you live in the Chicago Suburbs, I would highly recommend trying this if you ever get the chance! But first, here are some tips:

Choose the right day and time.

  • Pick a day that isn’t going to be cloudy and gloomy (unless you’re into that)
  • Go when the city won’t be completely empty, it’s not safe to walk alone during those times

Dress accordingly.

  • Check the weather and be prepared
  • Wear comfy shoes


  • Not a suitcase obviously,  but I brought a water and a portable phone charger

Take the Metra.

  • Very affordable
  • Don’t have to worry about finding parking downtown
  • I find train rides enjoyable because I can just listen to music and read a book on the way

Bring cash.

  • You’re probably going to need to take a cab at one point, always pay with cash


  • Listen to music while you’re walking
  • I found that this helped me concentrate more on myself and my thoughts
  • For safety reasons, whenever you feel like you’re in a “sketchy” area, ditch the music


  • Pick your favorite place to eat
  • Eat outside if you can
  • I went to the Shake Shack on Michigan Avenue and sat outside by myself, with my food. I thought I would feel weird about it, but it was actually kind of nice being able to admire the view of the city while I ate and listened to music.


  • Fully take in the city and enjoy every minute you’re there

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