Cocktails in Chicago: A Vacation Guide

Many times when I travel I get many of the same comments … what was the name of that resturant you ate at? What was the street where you took that photo? Can you share your fave spots in the city? To that end I create vacation guides. I have one for Jamaica here, Maine here, Ghana here and even Spain here

I was in Chicago a couple of weeks ago for my friend Oyin’s wedding (see gelé story here) and I took the chance to see one of my favorite cities. If you’ve never been to Chicago, think of it this way: if Boston and New York had a baby … Chicago would be the product. Chicago has the grandeur of New York with the incredibly tall and impressive buildings and also has that Boston charm and historic feel. It is also very clean …. which unlike New York is always a welcome change.

WHAT TO DO

Skydeck Chicago at Willis Tower

The skydeck at the Willis Tower has always been on my bucket list and I finally got to go! Architected by Fazul Khan, the Willis Tower has 103 floors and stands at 412 meters or 1353 feet. Yeah … pretty high up! The skydeck area is literally a glass box that you can walk into and view the entire city from. The views are incredibly breathtaking and the thrill is that the box that I mentioned is completely glass! So … if you are afraid of heights – this one might be one to pass. 

Blogger tip: check the weather and cloud cover before you visit the skydeck. The perfect insta shot requires little to no cloud cover. You also only get 30-60 seconds for photographs so figure out your poses before you get on the deck!

The Bean

If you have ever heard of Chicago, you most likely have heard of the bean. This is one of my favorite places to visit as it’s located close to many of my favorite eateries and it has incredible city views. It’s also great for people watching. 

Blogger tip: If you are looking to make this an insta worthy moment, come to take some pics very early in the morning – like before 7am early. The bean gets very crowded very quickly!

Rent a boat

Chicago is an adult playground. … if you know what you are looking for! My friends and I rented a boat through Boatsetter and spent an afternoon sailing, dancing and enjoying the Chicago skyline! There is plenty to do and see. What you have to figure out is based on your length of stay … how many fun activities can you squeeze in?!

Blogger tip: rent the boat in the late afternoon so that you can enjoy the gorgeous Chicago skyline in the sunset!

Where to eat

One of the things that Chicago is known for is some good food! My friends that live in the city constantly rave about the many options that they get to enjoy because they live there. From their famous deep dish pizza to Jeni’s Ice Cream, Chicago has a ton to offer for the culinary traveller. 

Blogger tip: plan all the locations that you would like to eat at before you get to the city so that you can know whether you have some insta moments in between! 

Binja the Africancocktail photograph of Jeni's Splendid Ice Cream Parlor in Chicago Illinois
Binja the Africancocktail eating ice cream in Jeni's Splendid Ice Cream Parlor in Chicago Illinois
Binja the Africancocktail eating ice cream on the steps of Jeni's Splendid Ice Cream Parlor in Chicago Illinois

There are tons more to do and see in Chicago … here are some of my faves! 

More to do …

  1. Museum of Contemporary Art 
  2. The Art Institute of Chicago
  3. Millennium Park
  4. Navy Pier 

More to eat …

  1. Yolk
  2. Angry Crab
  3. Beatnik
  4.  Nando’s
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