A brown girl's travel itinerary to Chicago
Windy City - Chicago
Chicago or Windy City as they say has been one of my favorite or more so the most convenient place to be on weekends, specially considering the fact it is 531 miles from my home, literally.
Most of my plans are impromptu not just because I am working full time but also because I spend more time thinking of going for a trip then actually planning the itinerary.
This one trip to Chicago is literally from one weekend, where I woke up from my dream, having this uncontrollable desire to pose at the Sky deck Ledge followed by immense wanderlust.
The trips I have been to, including this one are more about experiencing new things and definitely checking things off from the bucket list.I’ve put together a couple of things that I visited and one should definitely while in Chicago.
Day 1:
So it was a Friday and we drove all the way from Kansas to Chicago. It was a long 8 hours drive, but can’t complain I have always loved driving.
Checked in to Super 8 by Wyndham, a small tip - This place is in a really safe neighborhood, is affordable and 30 minutes drive to everywhere you ever want to be in Chicago. Saves you some money there.
Saturday Morning was going to be eventful day, since I had a couple of things on my mind to visit.
I started with having the Famous Chicago Deep Dish Pizza at Giordano’s . Too cliche but, Are you even in Chicago if you don’t try the deep dish pizza ? Well, it was lip smacking for sure. Also, don’t forget to try their Bruschetta, it has one of the best flavors of Balsamic Vinegar and fresh mozzarella.
Giordian’s Deep Dish Super Veggie Pizza
Bruschetta to serve my appetite.
My next spot which is walkable distance from Giordano’s was Cloud Gate or popularly known as Chicago Bean. Not only it is an architectural wonder but also a spot for getting the perfect shot for your instagram. Since Chicago is windy and chilly for most part of the year, it doesn’t hurt to pick a hot chocolate or coffee from the amazing cafes in the neighborhood. I personally recommend visiting Drunken Bean Cafe.
Also, while you are going places don’t forget to take a stroll down the Magnificent Mile in Chicago and appreciate the architectural wonders. It has amazing landmarks including everything from your favorite retail stores to hotels. And while you are at it don’t forget to stop by the Michigan Avenue Bridge and the crown fountain and pose.
My next destination was the famous Chicago River Walk. The riverwalk is usually closed and also not the best time to visit from December to March mostly because its covered in snow. I have been to Chicago both in November and May and from what I can say, the city is chilly for at least 7 months in a year.
We spent some good 25-30 minutes taking a walk down the Chicago river walk and took a long walk to Saks 5th Avenue covering all major Chicago Landmarks including Trump Towers, Wrigley Building and many more.



Chicago as we know is famous for its amazing skyline and what’s better to experience the thrill of it then viewing it from a thousand feet. Our next destination was 360 Chicago. I highly recommend doing the Tilt, It costs a couple of bucks more then the General Admission Pass but its all worth it. Roam around and experience the view from each side of the building. It offers the view of gold coast from one side and Chicago city on the other.
Also, before your trip to Sky Deck make sure you have a pose in mind. You literally get 90 seconds to pose at the ledge and you have to make sure you make that insta worthy.
Third and final day of the trip, I decided to go all touristy in Chicago and learn something historical about the windy city. I hopped onto the Chicago River Boat Architectural tour and not only was it breath taking because of the views but was very informative too. You do spend a little extra bucks there but its going in the right spot. The architectural Tour is a must do for history enthusiasts, just grab on some beer and go across the windy city!!
Chicago 2018 - River Boat Architectural Tour.
As the trip was coming to an end, I did have some checklists on my mind which I had to visit before I was back to my coding life. I discovered this Game of Thrones Themed Cafe in Chicago and the GOT Fan in me could not resist, I stopped there for a couple of drinks which by the way were really refreshing.


The 2.5 days trip was coming to an end, and it is never a good feeling. This was my first time to Chicago and I pretty much made sure I cover everything on my list. I was a little ambitious considering the amount of time I had, but that’s the thing about travel, There’s nothing like too much of travel.