Do’s & Don’ts: Chicago Edition

Hello Everyone!

Slowly but surely I plan on making Miami Obsessed a travel and fashion blog. In that process I decided that an important step would be to offer my tips and tricks when it comes to certain cities. Today I want to share my (AMAZING) Chicago experience. I will be describing Chicago in the winter because that is when I visited.



  • Make sure to pack thermals and warm clothing because Chicago winters are no joke and the wind is unforgiving. This Miami girl was freezing!
  • Invest in a CityPass — it includes the Shedd Aquarium, the Skydeck (which isn’t for everyone), and The Field Museum just to name a few. The CityPass pays for itself and you get to visit all the main tourist points in Chicago.
  • Try Chicago style pizza. I, personally, did not enjoy it because I am not a fan of sauce but it’s great to say that I tried it.
  • Go in the “off-season” because Chicago can get packed and quickly.
  • Visit the Magnificent Mile! If you’re a bargain shopper like I am, you need to visit the TJ Maxx and the Marshall’s. The quality is so different.
  •  Have appetizers at the Purple Pig — we really enjoyed our time there and we met some interesting folks.
  • Drink the most delicious hot chocolate you have ever had at Dollop Coffee Company  — their chocolate chip cookies are also life changing. (The irish pub next door makes the best hash for brunch. I wasn’t blogging then so I forgot the name, but I know it was amazing.)
  • Take some time to visit the Navy Pier. Definitely an interesting sight and you’re close to the Bean!


I took this from the John Hancock building. If you are not a fan of heights, do not eat here and do not visit the Skydeck.


The Adler Planetarium is where I’d have my wedding if I lived in Chicago. You can tell that a lot of thought and detail is put into enabling visitors to interact with their exhibits. (Fun Fact: You get a ticket to their space show when you buy the CityPass!)


  • Walk around without a lip balm. You will seriously hate yourself for not moisturizing your skin and your lips. The wind, like I said, is unforgiving.
  • Jaywalk. In Chicago this is apparently frowned upon.
  • Visit any of the viewing building if you are afraid of heights or elevators. It takes a minute to get to the top of the SkyDeck and it takes another minute to get back down. You can visit the “Tilt!” attraction if you really want an adrenaline rush — I passed on that.
  • Expect to have cell signal when you’re high up in the buildings.
  • Only drink Starbuck’s coffee. Chicago has delicious little coffee shops that allow you to explore.


If you have any questions — you can email me at: OR visit me on Instagram (@miamiobsessed)!


Disclaimer: This post is not sponsored. These are my own opinions and anything I suggest purchasing in this post, I purchased with my own money.



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