I love Chicago! I love how busy it is. I love riding public transportation and walking every where. I love the shopping and the museums. I love how close it is to home. And I really love the food!!
I had only been to Chicago for work so this was the first time I was able to take my family. To make it even better, we got to visit one of our favorite families – the Konc family. The Konc’s used to live a few doors up from us and since we have kids around the same ages we all became very good friends. Then they moved to Minneapolis. So we flew out to see them and explore Minneapolis. Then they moved to Atlanta so we drove to Atlanta to visit them and explore the city. And now they live in Chicago so we packed up the car and drove to Chicago.

Holland, Elliot, Roman, Andi, Joey and Winston – Friends for Life
We spent the first night at hotel in Lincoln Park. We arrived in the mid-afternoon so we decided to check out the hotel and freshen up. My son Joey has trained and worked for a circus since he was about 10-years-old. We had heard quite a bit about CircEsteem in Chicago so we scheduled a visit for him. While he was there, we drove around and let Andi take pictures at places that are in the show Shameless. It rained a lot that night so we decided to grab dinner at a diner close to our hotel and call it a night.
The next day we hit the Museum of Science and Industry. We spent several hours at this amazing museum. There were a lot of hands-on exhibits that even entertained me, my husband and two teenagers. My favorite part though had to be the U-505 Submarine. It’s a real submarine. My husband was in the Navy so it was amazing to see something like this up close.
That night we headed to the Konc’s homestead where we spent the next three nights with Amanda, Deacon, their four children and two dogs. The live in the Wrigley Field neighborhood. This neighborhood is really cool! I noticed the amazing architecture as we walked around. The Cubs Stadium was obviously my favorite. The neighborhood is also filled with cute shops, restaurants and bars.
We visited the Willis Tower (Sears Tower) and walked out on the Skydeck ledge. The view from the ledge was beautiful. Heads up though: the wait to get to the Skydeck and the ledge can be extremely long. We waited about 90 minutes to get to the Skydeck level and then about another 30 to go out on the ledge. It was worth the wait though.
Hitting Millennium Park is a must. Cloud Gate (the Bean) and the Crown Fountain are extremely unique and worth seeing. This is also a fun way to spend an afternoon without spending any money. The Shake Shack is a great spot to grab lunch and is right across the street from the Bean.
We also visited the Lincoln Park Zoo after having breakfast at Yolk. The zoo is small compared to Cincinnati but it’s free. We have also made it a tradition to visit the zoo every time we visit the Konc’s. BTW, Yolk was delicious too.
We rode the Ferris Wheel at Navy Pier. I was a little nervous about this but it was actually a lot of fun for all of us to be in the cage and look out over the water together.
The Art Institute of Chicago was inspiring. I will be honest though… the adults enjoyed this much more than the children. Andi, who is 18, and Holland, who is 15, pushed for this to be on our agenda but were done after the first hour. The boys were only into it for about 30 minutes. It is a very large museum and took quite some time to get through but I had hoped they would enjoy it as much as I did.
We enjoyed a fabulous dinner at Portillo’s one of the nights. This was definitely our cheapest meal of the trip but one of the tastiest. I had a Chicago style hot dog and fries. I probably could have eaten two hot dogs but I didn’t want to wait in line again. This place gets really busy and is not a sit-down kind of restaurant. You wait in line, order and then wait for your number to be called. You want to send one member of your party to grab a table while the rest of you wait. It is absolutely worth the wait.
We also got Chicago style pizza one night and I honestly can’t remember where it was from. It was good but it was not Giordano’s. Giordano’s is definitely my favorite place to get pizza in Chicago. Note that there is usually a wait there as well but you can order while you wait.
All of the activities were a lot of fun and the food was great but the best part was being with our friends. Honestly, we can just sit around the house with them and have a great time. The next time we visit, I want to hit the River Walk and take a boat tour!