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

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 one and two.

Last time, we loved on some art, some architecture and some Dominican Sisters. Our final day, we had no choice but to go big!

We started our day early with a hearty breakfast at the Bongo Room. Anna-Laura feasted on an amazing pineapple-upside down flapjack and I devoured an asiago cheese-mushroom-ham omelet. Dee-licious. It’s about now I’m starting to realize just how important food was on this trip.


It was just enough fuel to prepare us for a spectacular morning at the Museum of Science and Industry. We arrived shortly after opening and hit the U-505 submarine tour, the first one of the day. Absolutely fascinating. The City of Chicago is now home to a German submarine, fully restored and it is huge! Anna-Laura told me it was her favorite part of the whole trip. Here we are, sitting in the hull. I think she looks so incredibly grown up in this photo. {sniff}



The rest of our morning was spent learning about vortexes, healthy eating at YOU! The Experience and testing out our flying abilities in the flight simulator. I have to be honest, when we visited Disney in May, Anna-Laura was not a fan of the simulator. But here? She loved it! Wanted to do it again, even.




My only regret is that we didn’t spend more time at this off-the-hook museum. There was so much to see and do. The interactivity of this place blew me away. We loved it! Just before we walked out the door, I got a text from Scott telling me the Austin airport was closed, due to flooding. I got a tiny bit nervous, but texted him back and told him our flight status was still showing the green light. Famous last words.

Then, it was off to test our fear of heights at the Willis Sears Tower. Sorry, just can’t bring myself to say anything else. We got our 65-degree, sunny day and the view was SPECTACULAR! Look at that water. Those clear skies. All those tall buildings. The City Pass allowed us to use the Fast Pass lane (trust me, I looked around for Mickey and my Magic Band) and walk straight through security and onto the elevator. Less than a minute, and a few ear pops later, and we were at the top.



All along, I thought I might be the one to walk out on the Skydeck while Anna-Laura hung back. Aaaaand, I was wrong. She walked out there like a boss and started taking pictures. I was totally fine until I looked down. Not gonna lie. That took one big deep breath and “I can’t believe I’m doing this.”




Whoa. Nelly. It appears 103 floors up is, um, high.



After finding our stomachs, we hit the gift shop and found *the* key chain. It’s a bit of a 10yo trip tradition that Will started. He found one of those light up key chains that blinks “Mom” and I use it for the mailbox key. They usually fall apart just in time for another 10yo trip! We were started to lose faith in Chicago, until the Sears Tower happened. Success!

Then, it was off to one last spot before lunch, The Bean. Our Über driver ended up dropping us off at Maggie Daly Park, but the walk over was just spectacular. We didn’t mind one bit.



And this happened. No coats, all sunshine and some major smiles. In the spirit of full disclosure, this photo almost didn’t happen. Anna-Laura did not want to go to the Bean, but I really did. She started to get the sassy 10yo look, so desperate times, desperate measures. I promised her candy at the airport. Done and done. I don’t regret those Skittles. One. Single. Bit. Because this photo? My favorite of the trip!


We hit Portillo’s for a famous Chicago dog and inhaled it. Like, we were only there 10 minutes. I was very anxious about Friday afternoon traffic and didn’t want us to miss our flight. We paged Über once more and had the scariest ride of my life. I’m not joking when I tell you I feared for my life. We picked up another driver to the airport and he was a gem.

After a pretty quick TSA check-in, we discovered our flight was saying on time, but the desperate texts from Scott were saying otherwise. I decided I didn’t have time for that crazy, so I immediately called the airlines and begged for a flight to another airport, any airport, in Texas. Turns out there was a Houston flight leaving in an hour and they had two seats left. DONE! A few frantic texts to Scott, a Facebook post asking for a ride and a place to sleep later, and we arrived in Houston. We were exhausted, but grateful for great friends and a little “Back to the Future” movie to keep us occupied on the flight home.

At 0700 the next morning, our friends loaded us, and all our luggage, and we headed to College Station for the A&M game. It wasn’t originally on the trip plans, but isn’t it fun when providence provides you with a beautiful ending? To everyone who asked, no, we did not pack Aggie shirts. Scott was kind enough to bring them to us. I mean, we’re prepared, but not that prepared!

TAMU, blog

To my sweet Anna-Laura…

This trip with you was beautiful, in every sense. The food, the conversation, the things we saw, the people we met – it was all lovely. But, for me, it was the little moments I witnessed. The moments we shared, just the two of us, that no one else experienced but us. I will remember them for the rest of my life. You made me the mom of girls and I am eternally grateful. Thanks for the one of the best weeks of my life and welcome to TEN!

Lessons learned and a few travel tips

  1. Plan ahead. We knew our destination several months before Anna-Laura turned ten in May, but we also knew we wouldn’t be traveling until the fall. We kept our eyes, and our computers at the ready, out for any good airline deals. When Southwest Airlines ran their big sale in early June, we logged on only to find the server kept crashing. In response to that major snafu, several airlines jumped on the sale bandwagon and we scored a direct flight with a lower fare on American. YES!
  2. Be flexible. We have some beautiful friends who live in the Chicago suburbs and they were kind enough to pick us up from the airport and put us up for the night. Because the drive was a good hour+ in to the city, we opted to get a hotel room for the remainder of our stay. But, because we didn’t want to pay an arm and a leg, I took the advice of a blog reader and logged on to HotWire. You select a general area (we chose Water Tower near the Mag Mile), approve the room cost and then book the hotel. It’s only after you pay when you learn which hotel you landed. Turns out our hotel was a total winner of a boutique hotel with a fabulous location and lovely staff. Total win-win.
  3. Maps are your friend. I wouldn’t say I’m directionally-challenged, but my husband will. Thank the good Lord for Google Maps and the City Mapper app. Before we left, I had a Word document where I listed all the places we wanted to visit (that, after polling the blog and Facebook about all the must-do’s). Then, I pulled them all up on Google Maps to get a better sense of what to do where, and when. That helped tremendously. We never back-tracked and because I knew where things were ahead of time, that helped me make modifications to our plans without wasting time. I put that document as a note in my phone and relied heavily on City Mapper while we were there to map our walks. It worked perfectly. And it’s free!
  4. The City Pass was worth every penny. At first, I wasn’t sure we’d really use it since we couldn’t hit every attraction on the pass. However, it allowed us access to Fast Pass lines, extra exhibits and audio tours that really enhanced our experiences. I purchased it online before our trip, too. We don’t have a museum annual membership so the ASTC passport didn’t really apply to us.
  5. Check your flight status. HA! Thank goodness family texted us about the airport closure in Austin and encouraged us to book another flight to a different airport. Otherwise, we would’ve been camping out at Hotel O’Hare. No thank you.
  6. Eat local. There was only one meal we had to eat fast food. The rest of the time, though, we relied on locals and friends to steer us in the right culinary direction. Just like it would be criminal to come to Texas and NOT eat BBQ or Tex-Mex, we felt like we had to dine on some great dogs and deep dish to call the trip authentic. I’m so glad we made that a priority. What fun!
  7. Be nice. Our hotel let us check in a whole eight hours early. The Peninsula Hotel paid for our afternoon tea. Our Über driver waited for us even though he wasn’t required. Time and again, lovely people did such nice things for us simply because we were kind. Life’s too short to be rude.



  1. Jackie on November 11, 2015 at 8:34 am

    Sounds like a fabulous trip! And so many great memories you created for her.

    You were so lucky to get re-routed to Houston and had friends that could help you as well.

  2. Nicole on November 11, 2015 at 8:38 am

    You’ve inspired me. I think this whole 10-yr-old-trip thing is a wonderful tradition! My son turns 10 next summer, and with a baby being born just a few months before his birthday, the 10 yr old trip might be a great pick-me-up for him (and let’s face it… for Dad, too, since our son would definitely pick him to go). Thanks for the inspiration and taking us along on your trip 🙂

  3. Madeline on November 11, 2015 at 10:34 am

    I know I said this on Instagram but I feel like the biggest fan girl of your trip. With the exception of Shedd you hit every major Chicago thing I love. Seriously. We don’t even live that far from Chicago and I am now desperate for another trip!! Your family is inspiring me to plan for a 10 year old trips for my kids. Such a great idea with wonderful memories.

  4. Pamela on November 11, 2015 at 1:22 pm

    I loved reading about this trip! You’ve inspired me to do a 12 year-old trip with our kids.

  5. Abby on November 11, 2015 at 2:01 pm

    Loved your trip! So much fun! We are kind of copying your idea for our daughter’s 12th birthday! Off to the big apple!

    We are HUGE fans of Priceline and Hotwire. We’ve never had a bad hotel experience and get to stay in much nicer hotels than we can actually afford!

  6. Mary Wilkerson on November 11, 2015 at 2:39 pm

    I like this ten year old trip idear— it’s kind of the perfect age huh? Do you have a post explaining why you decided on 10 and how you came to the decision to incorporate this into your family? And if it’s always one parent who takes the child? So many questions 🙂

    • Kathryn on May 15, 2016 at 11:49 pm

      Shame on me for not replying! Just now seeing this! You know, we knew two other families who did a 10yo trip and it just seemed like the perfect age. And it is. Those two families were huge influences on our faith life and this trip seemed like such beautiful one-on-one time with our kids. The birthday kid gets to choose the parent, but so far, it’s been boys choose dad, girls choose mom. Going forward, I think we’re just going to make that our MO. It feels right so we’re going with it. Hope that answers them all!

  7. […] 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 one and three. […]

  8. […] 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. […]

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