Chicago, Illinois

Take a trip around Chicago with us as we explore one of our favorite cities!

Anytime I am given the opportunity to travel close to “home”, Wisconsin is where I grew up and my Cookie now lives there, I immediately text her asking if she is up for an adventure. She of course texts back, “Of course, when and where and I will be there!” This is such an amazing thing that we have together. We are 30 something year old's and long distance friendships can be hard. You have to make it a priority and take any chance to meet up when you can. A lot of people our age always say, “I just don’t have time anymore with everything going on in my life.” I think that everyone lives have changed significantly from college with the most important decision I had to make on a Thursday night after bar close is if I wanted Qdoba or a frozen pizza at home. We are all now adults with careers, significant others, kids and pets in our lives. But the biggest difference is if you make that choice to put friendships just as high up on your priority list just like those other things I listed. So long story short, my hubby had a job training in Chicago in March and I knew I was going to tag along and meet up with my favorite Cookie because we are both always up for any adventure big or small. I patiently waited at the Starbucks inside the Kimpton Hotel Gray for her to get in from taking the train from Milwaukee to Chicago to meet me. We sat down to plan our our day in the city with our go to basic bee drinks, a green tea lemonade for me and a vanilla bean coconut milk latte for her. After going over our options we decided to be those tourists all day checking out everything everyone wants to see in while they are in Chicago. Our first stop was Revival Food Hall to grab a quick snack before we headed out for the day. This is a super cool spot that has multiple food vendors so it will certainly have something for everyone. We settled on Lito’s Empanadas and it was a great choice. We each ordered 2 empanadas each, 1 sweet and 1 savory. They were delicious, super flaky and flavorful.

After a quick outfit swap, we headed out on foot to find Cindy’s Rooftop Bar inside of the Chicago Athletic Association Hotel. This was by far our favorite stop of our adventure filled day. We took the elevator up to the 13th floor, took a step out and was greeted with the most picture perfect bar. They had a terrace that you could go out on with fire pits and the best part, it overlooked Millennium Park! Of course we were there to have a couple cocktails and enjoy the view. I picked an Old Fashioned and Leanne chose the Coast to Coast.

Next we crossed the street and made our way over to Millennium Park where I immediately was scolded by a security guard for standing on a picnic table to snap a picture of the iconic Bean while Leanne giggled and tapped my leg to get down because I didn’t hear the guy tell me not to do it! LOL...great looking out for me Cookie! I have been to Chicago so many times prior to this but had never snapped a picture with The Bean. I can now check this off of my bucket list!

After we got enough pictures with The Bean, we hopped in an Uber and made our way to Navy Pier (another place I had never been to). We both decided it was a must to go on the famous Ferris Wheel to fulfill our little girl hearts with joy. Not going lie, after the first 2 rotations we were over it already but went around 1 more time for good measure! The views were beautiful, you could see out onto Lake Michigan with all of the snow and ice covering it on one side and to the other, the best Chicago skyline views!

We were starting to get hungry so we decided to go back inside and see what we could find for restaurants. Of course we had to go to Giordano’s for a classic Chicago staple: DEEP DISH PIZZA. We ordered a pizza to share with a couple more drinks. When the pizza arrived I made sure to test its “cheese pull” ability and it passed with flying colors. Trust me, it is worth the extra along time it takes because the crust was super buttery and tender with plenty of cheese, sauce and toppings to back it up.

Our next stop was another Chicago must have: Garrett’s Popcorn. A short Uber ride from Navy Pier we made it to Garrett’s where again I almost got ran over by a gentleman walking by while I tried to capture the best photo of the sign outside of their store. Thanks to my Cookie she saved me once again. Once inside we were overwhelmed with so many popcorn choices but of course we had to go with the obvious choice: Chicago Mix! If you are not from the Midwest or familiar with Chicago mix popcorn it is the best combo EVER! Cheese popcorn mixed with caramel popcorn, we were in salty and sweet heaven. My tip is to eat a piece of each at the same time for the ultimate popcorn eating experience! If you are not planning a trip to Chicago soon but want to experience this popcorn combo for yourself, you can order it online and they will ship it to you!

On to the last leg of our Chicago adventure. We decided to walk back to the hotel because it was only about a mile or so and it was a beautiful sunny day in Chicago. On the way back I spotted The London House. We were a little parched and in need of 1 more drink before the day was over. We headed upstairs to the rooftop bar (London House on 21) and ordered some sparkles to celebrate the end of Cookie day! If you have never been to the London House, they have the best rooftop bar with gorgeous views of the river and downtown.

Before I could let Leanne leave, I had a surprise gift for her. I had bought us 2 matching luggage tags to celebrate our new blog and travel adventures together. They say “ And so the adventure begins.” If we only knew what was in store for us with that quote but that’s a story for another blog post! No matter the amount of time you have to spend with your best friend who lives across the country or maybe a couple hours from you, it’s important to make the time to make it happen! I hope this helps our followers realize what you can make happen in a few short hours with your best friend. Being tourists, laughing, catching up and just spending some quality time together can be the best thing until you can plan another trip together. Happy Travels!

Calla