Daycation : Chicago Travel Guide

Sometimes you gotta treat yo self to a lil vacation. The past couple months for me has been full of new adventure and quite frankly I NEEDED a break! Even if it was just for a day.  

So I decided to make the three hour drive northwest to Chicago. And because it's no fun being alone, I brought my bf along. (He was so happy to be chosen as my shopping buddy.)  

I planned to leave at 6:00 am. If you know me (I am NOT a morning person) then it won't be a shock to you that I didn't leave until 6:30 am. BUT I forgot that Chicago was on a different time than Indianapolis so really I left thirty minutes early.  (Wooop wooop!) 

We arrived in Chicago about 9:30 am and parked in the South parking garage. It's right by Millenium Park and the Chicago School of Art. It was the perfect place to park in my opinion. (Also only cost $16 for the whole day.) 

First stop: BRUNCH  

@TheBongoRoom - Known as a local fave this was first on my list. It's always good to start with a good breakfast. It will give you plenty of energy for the long (but fun) day ahead. I decided on the croissant sandwich, which did NOT leave me disappointed. It was larger than what I was expecting and it came with their homestyle potatoes. Easily those potatoes were the BEST part of the meal. (Potatoes are also my weakness.)


We then hopped on the L and headed to our first location.  Being from Indy, I am not used to a public transit system so riding on the Loop was part of the fun for me. I would recommend you buy the day pass for $20 and hop on it every chance you get. 1. It will save your feet. No matter how comfy your shoes are, your feet will start to hurt after walking on them all day. 2. Seeing all the different people, from different kinds of lives all in one place is pretty cool. 3. It's a part of Chicago life. So embrace it. 


 @TheWillisTower (aka SearsTower) 103 floors above the street and you will start to feel pretty small. The Willis Tower is the tallest building in the Western Hemisphere; standing taller than the Empire State Building and the Eiffel Tower. This was by far the best view I have ever seen. But I am a city girl so those of you who prefer the beach or the woods might not fully agree, but you'll still think it's pretty cool. The Skydeck is open from 10-8. We arrived by 10:15 and only waited about 20 min to get through the line to the 103rd floor. It does cost $23. BUT if you want to go up during the day and then again at night the cost is $33. *I highly recommend you do that. You will get the most bang for your buck! 


Once you get to the top I suggest you go straight to the ledge. The later you go those lines get really long. We waited for almost 30 min. It is definitely worth the wait though. 

Next stop: CAFFIENE



*NEED I say MORE?!* This is the cutest coffee shop for a little coffee / rest your feet break. 

@TheCloudGate (aka TheBean) @ Millenium Park is one of the most popular tourist attractions in Chicago. We made it there around 3:00 and the crowd was reletively small. If you have never been to Chicago, it is a MUST photo op. 


By this time we were close to the car so we took a quick break and headed to put some of our things up. It was the perfect midway point. 

Lastly needed: ENERGY BOOST

@ShakeShack By 4:00 I was needing some food and this was calling my name. How can you just walk by and NOT get yourself a burger & fries?! And of course I also treated myself with a shake. You can't go to Shake Shack WITHOUT getting a shake! 


It gave me the perfect amount of energy to conquer the next adventure. 

@MagnificentMile , although is not really in my budget, I still enjoy taking a walk down Michigan Ave & looking in all the stores. This was for sure not my boyfriend's favorite part, but he appeased me and even made it more enjoyable.  


Our Chicago daycation had come to an end. With our tired eyes (and feet) it was time to hop back on the train and head to the car. 

If you take full advantage of Chicago there will be lots of walking so be prepared for what the weather will be. It isn't called the Windy City for nothing! 

Safe travels,