Touring in The Windy City

Unexpected Vacations to Chicago

As you know if you read the ‘about me’ section of my blog, I consider myself as a very lucky person. One of the reasons why, is because I have traveled many times for free! This time, I won an all-paid trip to Chicago!  It was unexpected and I only had a few days to prepare for it, but the timing was perfect, I’m a hot weather lover so going by the end of July was all I could ask for. I love New York -like everybody else- so I thought Chicago was going to be an amazing city as well. I wasn’t mistaken.


The Windy City has many to offer, but I had only a weekend to enjoy it. So, without much planning I just head out from the hotel and wander around. After my experience, I recommend you these 7 things to do in Chicago:

1. Visit The Millennium & Grant Parks

First things first. Ever since I watched the movie Source Code, with hottie Jake Gyllenhaal, I wanted to visit Cloud Gate, so, of course, this was the first thing I did. I stayed at the Hyatt Regency Chicago on Wacker Drive so after a short 10-minute walk to Millenium Park, I was there! The sculpture is pretty amazing and worth spending time at, you can take many creative and crazy pictures.


Next to Millennium Park you’ll find Grant Park, a nice spot to enjoy the weather. Make sure to visit the Buckingham Fountain, which is huge!



2. Enjoy The View From Skydeck

One of the things I like about major cities is that they usually have big tall buildings, so I couldn’t miss the opportunity to go up one. I asked around and people suggested to visit Skydeck at Willis Tower rather than 360 Chicago because of the views, so I did. I chose to go up at night, which was a good decision because the line to get in was very short. It was an incredible experience, the city lights were unbelievable! You can walk all around the building plus you can stand on a glass floor overlooking the city! Creepy but worth it!


3. Eat Lots of Pizza

Dip dish deliciously famous Chicago Pizza. Do I need to say more?


4. Walk Around Navy Pier

If you like photography like I do, then take a walk down to Navy Pier, you’ll have Chicago’s skyline all for yourself. The view of Lake Michigan is quite nice, which reminds me you can also enjoy it from a Ferris Wheel (Currently the Ferris Wheel is being replaced for a bigger one in 2016).


5. Party in Boystown

For me a little bit of party is a must when traveling. So make sure to visit Boystown! This neighborhood is one of the largest gay communities in the United States. I was happy to see that all of the clubs had different types of crowds, thumbs up for diversity! After hoping in different bars, Hydrate was my favorite.


6. Have Breakfast at Wildberry

After a night of clubbing all I wanted was to have breakfast, so I went to Wildberry Pancakes & Cafe. The line was long, I had to wait almost for an hour, but let me tell you it is totally worth it! Pancakes are to die for.


7. Go Shopping

I couldn’t leave without shopping, Michigan Avenue is the perfect place to do so. You’ll find all type of stores throughout the avenue and also other streets around it. If you are a big spender, then you have to go to The Magnificent Mile, which is an upscale section of the avenue. Do yourself a favor and visit Dylan’s Candy Bar!


I know there’s more to see in the city, so I’m hoping to go back soon! What else would you recommend doing in Chicago? Leave a comment below!