Chicago With Teens – Day 1 Train Ride, Deep Dish Pizza, Fun Treats!

Share Our Happy!!

Now that our oldest is away at college, I feel a strong nagging  as we approach losing our middle daughter to the commitment of adult life. As each year passes, traveling as a family becomes more and more difficult. I want to do as much as possible with the time we have, while they are still younger. 

Our trip to Chicago was the outcome of shear determination. Once my mind was made up to get there, nothing was going to get in the way.  Why had I decided I had to get to Chicago? Well, long story short…… Matt hunts in Michigan UP every November. He suggested we meet up in Michigan to spend Thanksgiving together. I agreed, but Anna had to be in Indianapolis the weekend before. I try my hardest to stretch out our trips up to see family, so I decided to head up early, and drive Anna to and from Indianapolis. Instead of driving back to Michigan, Jojo and I stayed with my Aunt Sure in South Bend. This sparked the idea of “Why not go to Chicago too?” 

Train Ride

In order to have as much time in Chicago as possible, we hopped the South Shore Line commuter train from South Bend to Chicago. It is reasonable, more relaxing than driving, and no worries about parking in the city. 

South Shore Line Commuter Train
Jojo and I on the South Shore Line
South Shore Line Commuter Train
Annie and I rinding the South Shore Line from South Bend to Chicago.

Where We Stayed

Once we arrived in the city, my friend Sandi brought us to her house, where she was gracious enough to let us stay for the next two nights.  She has been renovating an old home on The South Side for several years. We slept in the renovated basement, which used to be the carriage house portion of the home. It has the original wood staircase, and beautiful exposed brick.

Chicago Style Deep Dish Pizza

The famous Giordano’s was within walking distance from Sandi’s, so the girls and I walked over for dinner. Anna and Jo got to have their first Chicago deep dish style pizza. 

Giordano's Chicago
Giordano's Chicago
Giordano's Chicago

Fun Dessert

She also told us about La Michoacana Premium, right around the corner from Giordano’s, for dessert. They make gourmet popsicles. Anna had strawberries & cream, I had pistachio, and Jojo had cookies & cream. I could not believe how many pistachios were in mine!! They we delicious! 

La Michoacana Premium Chicago
La Michoacana Premium gourmet popsicles!!

Much more planning went into how, and when, we were arriving and leaving, than what we would actually do while there. I thank my Aunt Sue, and my girlfriends, Sandi and Kristi, for being so flexible during our travels. 

Chicago with Teens

Please share your hidden finds from Chicago. We would love to find new places next time we visit.

Share Our Happy!!

Julie Gazdecki

Julie is owner and founder of How We Find Happy. As an optimist, the name is perfect as we share the ways we find happy living in Florida, visiting breweries, spending time with our adult children, and getting away on some couples trips. As previous residents of Michigan, we still spend lots of time each year visiting our family up there, along with new and favorite places. My hope is to encourage others to spend time exploring this beautiful world, and finding happy in unexpected places.

9 thoughts on “Chicago With Teens – Day 1 Train Ride, Deep Dish Pizza, Fun Treats!

  • Donna Lynn Starling

    Love Giordano’s Pizza. When My son and I went to Chicago years ago we took the train from the suburb of Downers Grove into union station, walked around Navy Pier, and went up the Sears tower. Geat memory.

  • Teresa | Happymomhacks

    Taking the train into Chicago is the way to go. Traffic is terrible and parking is expensive in the city. The popsicles look great! I am gonna add it to my places to visit in Chicago. Thx for the suggestion.

  • Julie Gazdecki

    We love taking the train into the city. We have taken the train from Detroit to Chicago too. So much fun! Still have not done Sears Tower.

  • Julie Gazdecki

    It sure is the way to go. My first trip to Chicago in my 20’s I drove. Never again!!

  • Pam Jennelle

    Those popsicles look amazing. I’ve been to Chicago three times for about a week each time…never ate at the same place twice and never had a bad meal!!

  • Julie Gazdecki

    I don’t think I have ever ate at the same place twice either. Too many good places to check out!

  • Kendra

    Awesome! It’s good to see ideas for teens. Can’t wait to check out Chicago!

  • Julie Gazdecki

    It sure helps when the teens like to do the same things!! Hope you get to check out Chicago too!

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