The 10-Year-Old Trip to Chicago: Part One

When our children turn ten, we treat them to a 10-year-old trip. To catch up on the full story with Anna-Laura, read parts two and three.

The 10-year-old trip is legendary at our house.

It’s more than a milestone, or counting your age on two full hands. It’s an adventure.

Because we have six children, uninterrupted one-on-one time with them is precious. We don’t think that’s necessarily a bad thing, this sharing with other siblings gig, but we do think a trip with just one is worth saving our pennies. And so we do whatever necessary to make it happen. The catch? The child has to choose one parent for the trip, a destination and the place must include a plane ride.

Our oldest kicked it off with a trip to Washington, D.C., while our second chose New York City. Number three? She chose the Windy City. And me! Over the next few blog posts, I’ll be sharing what we did, what we learned, how much chocolate we ate and the thing she did that really, and truly, brought me to tears. The good kind, of course.

When our children turn 10, we treat them to a 10-year-old trip. It involves a destination and parent of their choosing. The time is filled with sweet memories, lots of laughs and an unforgettable trip with just one parent and one child. We love it!

Let’s dive into the awesomeness. You can also read parts two and three.

I felt like it took an Act of Congress to get us out of the house for the trip, everything squared away and “the list” of all the kid activities ready for my husband. He’s a stellar better half, but I couldn’t walk out the door without having everything settled. I know you moms feel me. Anna-Laura enjoyed a half-day at school and then I picked her up and off we headed to the airport.

Our outbound flight was slightly delayed. The only real travesty? Standing in the TSA line with the University of Texas volleyball team. I almost broke out in hives standing next to that much burnt orange. Fortunately, my knee pushed us into the TSA pre-check line and I’ve never been happier to switch lanes.


While we waited for the flight, we passed the time with Amy’s ice cream. Because, why not? We scored the extra leg room seats and no one beside us. We figured the best way to prepare for our trip to Chicago? Bueller? Bueller? Bueller? I had to explain away a few words, but how fun to watch that movie on the way.

“Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.”

Our sweet friends picked us up at the airport and hosted us for the evening at their home in the suburbs. They have four children and when we walked in the door it sure felt like home. Colleen cooked a mean chicken piccata and after the kids were in bed, we enjoyed a few glasses of vino and some good conversation. God bless you Peter and Col!

Peter’s office was right around the corner from our hotel, so he drove us into the city the following morning. It was a little chilly and rainy, but because I had been checking the forecast like a hawk, I made that our easy walking day.

Our hotel was one I acquired off HotWire. Let’s just refer to it as the cutest little boutique hotel, ever. MileNorth allowed us to check in to our room at 9:30am with no additional fee and I almost hugged the check-in clerk. Our first stop after dropping our luggage?

American Girl, on the Mag Mile.

After walking in and picking my jaw up off the floor, we enjoyed the entire two-story place largely to ourselves. The rain kept the crowds away and boy, was it awesome. There was hair styling, ear piercing, escalator riding, shopping and maybe some mild squealing. We were very grateful for that AG gift card from Christmas. We put it to good use. AG totally beat math class.




All that shopping made us hangry. For chocolate. Ghirardelli delivered with the Crissy Field sundae. Chocolate for lunch? Yes, please.


We made the walk over to the Holy Name Cathedral for noon Mass and had plenty of time before Mass to walk around the interior and admire the art, windows and architecture.



Anna-Laura kept asking me how long Mass would be and I assured her daily Mass was like “Sunday Mass-lite.” That was a beautiful half hour of peace and time together. We lit a few candles for your intentions and then journeyed back to the hotel, but not before stopping in at Tiffany’s.


The funny ha-ha there? When an older woman brushed past me and rows of diamonds in a huff and muttered, “I’m just so exasperated. This place has really gone downhill.” It took all I had not to let the laughter bubble out.

We originally planned to have afternoon tea at the Peninsula our last day and visit the Museum of Science and Industry our first day, but because of our flight departure time and the weather, I opted to switch the two and I’m so glad I did. After a little downtime and unpacking in the room, we walked the half block back to the Peninsula Hotel and found our seats for high tea.

Anna-Laura surely thought this was going to be the lamest thing we did. She admitted later she thought all we were going to do was sit at a table and drink tea. But, then she saw this and perked right up.



We felt very much like princesses that afternoon. Everyone greeted her by name and wished her “happy birthday.” {I guess they do read the comments on Open Table!} And, when the ceiling started to leak on me and the food, they felt so horrible, they brought us two extra desserts, paid for my tea and gave Anna-Laura the most adorable teddy bear. Three people came over to apologize! I kept telling them it was too much, but they were adamant about making it right. I cannot say enough nice things about our afternoon there. Class act, all the way. And, may I add this hotel is just stunning? It felt like a scene out of a movie.


After our scone and dessert coma, we decided to go in search of some more food, Garrett’s Popcorn! Evidently it’s legendary in Chicago, so we gave it a whirl. We thought the Garrett Mix was okay (caramel corn with cheesy corn), but we loved the buttery flavor. It served us well later that evening when we binge watched HGTV.

For dinner, we enjoyed a fancy meal at Baffo. I’ll admit that it’s really for the foodie. Anna-Laura and I liked it, but it wasn’t our most favorite meal. The staff was incredibly kind and even treated Anna-Laura to sparkling lemonade and me to sparkling something else. But, what happened after dinner really made my heart burst with love. As we walked back to the hotel, she noted how many homeless there were on the street corners. I told her I had noticed, too, and was really struggling with how best to help them. She perked right up. “Mom, there’s a Walgreens right around the corner from our hotel. I bet they have socks. Let’s buy them socks,” she said.

And so we did.

The most joyful moments of my week were watching her confidently and lovingly walk up to homeless men and women and ask if they needed a new pair of warm socks. The smiles she received from me were only outdone by the recipients of her generosity.

Anna-Laura, your heart is pure. May it always stay that way.

Tomorrow, we spy some mighty fine impressionists, almost chase down a boat and earn a cameo in a TV show. Almost.


  1. HollyB. on November 6, 2015 at 8:18 am

    Oh Kathryn, my daughter (our first girl; we’ve got two magnificent boys, too) was born exactly 4 weeks ago today, and I so enjoyed reading this post – the end made me tear up! I pray that my tiny Tess and I will share a similar relationship to the one you have with your girls, and that her heart will be as brave and generous as your Anna-Laura’s. Happy (belated) birthday, Anna-Laura!

    • Kathryn on November 7, 2015 at 9:44 pm

      What a kind thing to say – congratulations on your sweet girl!

  2. Brandi on November 6, 2015 at 9:49 am

    I have a friend who volunteered at a Chicago homeless shelter a few years back and while visiting, I spent an overnight at the shelter. It was life-changing. I am sitting here in tears thinking that just maybe Anna-Laura gifted socks to one of those men I met. God bless her!

    • Kathryn on November 7, 2015 at 9:44 pm

      Oh wow, I bet that was an incredible experience.

  3. Verdina on November 6, 2015 at 10:07 am

    Kathryn, you continue to knock it out of the park! Your children are so blessed to have you and Scott as their parents!

    Anna-Laura’s empathy for the homeless is so touching… she didn’t just muse about it; she DID something! God bless her )& you)!


  4. Beth (A Mom's Life) on November 6, 2015 at 11:20 am

    What a great trip! And your daughter has a big heart! What a kind thing to do.

    • Kathryn on November 7, 2015 at 9:43 pm

      She does have a beautiful heart. We had quite the week.

  5. Karen on November 6, 2015 at 11:53 pm

    Sounds like an awesome trip so far, but is her AG doll missing her pants????

    • Kathryn on November 7, 2015 at 2:21 pm

      She had a skirt on that just got a little moved up after sitting in the salon chair.

  6. sarah isis (@disisd) on November 7, 2015 at 9:23 pm

    What a great way to celebrate 10th birthdays! so so special. I might have to copy that idea… 🙂
    This photo diary and recap is amazing. It felt like I was there with you guys. Anna-Laura has a big heart like her mama.

    • Kathryn on November 7, 2015 at 9:43 pm

      Thank you! It was so much fun to document.

  7. […] ten, we treat them to a 10-year-old trip. To catch up on the full story with Anna-Laura, read parts one and […]

  8. Nicole on November 9, 2015 at 9:33 am

    Wow – that sundae!!!!!! Not good for this pregnant mama to see that this early in the morning. Now I want ice cream 🙂

    This trip sounds so great! And I love that you watched Ferris Bueller on your way there. Perfect movie option.

  9. […] ten, we treat them to a 10-year-old trip. To catch up on the full story with Anna-Laura, read parts one and […]

  10. […] have really come into your own this year. For me, our time together during your 10-year-old trip allowed me to see another beautiful side of your personality, your soul and your heart. It was a […]

  11. […] out of her mind excited. Admittedly, I am, too. You can read a bit more about our 10-year-old trips here, when Anna-Laura and I conquered […]

  12. […] off with a trip to Washington, D.C., our second chose New York City and kid three picked the Windy City. Clare? She chose me and Disney! I can’t tell you how providential the timing was for the […]

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