Dear Chicago: What I Learned, What I Love, & Everything In-Between

September 20, 2016

I’ve always heard a lot about Chicago; a city with a better skyline than L.A. and a cleaner version of New York, a city full of pride, good food and a diverse set of people, a city that everyone seems to love. So when the opportunity presented itself to visit the windy city I, of course, said yes.

Now that I’ve visited the city, I can confidently say that Chicago possesses a unique character, rich in culture, and packed with friendly people. I love a city where public transportation is easily accessible. A city where you can go from point A to point B with no problems at all because the public transit system is extensive and well thought out. In this city you’re able to grab a train ride to almost anywhere you want and with enough exploration you’ll be able to uncover little neighborhood gems. Each neighborhood is distinct in their own way, which can make it easy for someone to find one that is a perfect fit for them.

Processed with VSCO with f2 preset

I learned a few things while I was on this trip and I was able to have some really memorable experiences like riding on the frame of a SINGLE bike for 2 miles as my boyfriend pedaled. We received a mixture of smiles and confused looks from strangers as we passed them by. We even heard someone clapping as we moved along the streets of Chicago determined to get to Jimmy Red Hot’s, the best hot dog in Chicago. Once we got to our desired destination and I was able to taste a true Chicago delicacy I have to say was well worth it! It was the most bazaar, fun, yet, uncomfortable experience I’ve ever had. I’ll also never forget the way the skyline looked as the sun began to set while we sat near the lake and enjoyed some banana pudding and lemon bars. Sometimes some peace and quiet and beautiful scenery is all you need. Most of all, I will cherish the friendships I created with the people I met in Chicago. They are some of the warmest, down to Earth people I’ve ever met.


There are a few tourist attractions that I believe need to be done in Chicago, but as always, I believe it is necessary to do as the locals do. Here are the Do’s and Don’ts for when you visit Chicago:

Processed with VSCO with f2 preset



  • DO see the Sears Tower, now known as the Willis Tower
  • DO eat a hot dog at either Superdawg, Portillo’s or Jimmy Redhots
  • DO use public transportation and walk around. The CTA is a fairly well thought out transit system that can get you from point A to B in no time!
  • DO eat…a LOT!
  • DO leave room for spontaneity
  • DO see a live jazz band
  • DO make friends



  • DON’T make your itinerary too packed
  • DON’T go to the Willis Tower without buying your tickets online first. You will end up waiting for about 90 minutes just to get to the top
  • DON’T just stay in downtown, explore outside of that area
  • DON’T go to the planetarium or aquarium when there is an event. Look online first before you go because getting to and from the area will be too expensive or a long wait.
  • DON’T go out of your way to eat a deep dish pizza (Chicagoans love their hot dogs & Italian beef more than their deep dish…at least that’s what I was told.)



Sample Itinerary for a day in Chiago


Go to the Doughnut Vault for breakfast. Don’t wait too long or else the donuts will be all sold out!


Walk around downtown and explore a little


Willis Tower! Use your pre-bought tickets to cut the wait by at least half.


Lunch – Make the trek to Jimmy Redhots because it is worth it! Hands down, one of the best hot dogs I’ve ever had.


Rest or explore Logan square


Watch the sunset with the view of Lake Michigan and the skyline outside Chiicago’s planetarium. Maybe have a picnic and have some dessert while you sit by the lake.


If you’re still up for it go watch a live jazz band in a local bar.


Processed with VSCO with g3 preset

You Might Also Like


  • Reply Jeff November 27, 2016 at 9:56 pm

    Hi Camille, looks like you had an awesome time in Chicago! I love your idea of checking out the planetarium or aquarium when there is an event going on. For your readers that visit the city as a couple we always recommend checking out the planetarium on the 3rd Thursday of every month there is “Adler After Dark” where only guests 21+ can enter and they setup bars throughout the place. It’s fricken cool!! -Free Chicago Walking Tours-

    • Reply November 28, 2016 at 10:32 pm

      That sounds amazing! Thanks for the tip, Jeff. I’ll be sure to do that next time I visit.

    Leave a Reply