Childless in Chicago

Chicago, IL (2016)

John 1:3: All things were made through him, and without him was not any thing made that was made.

We absolutely loved being tourists in Chicago. Sure, we’d probably enjoy walking around any city without our young kids for a few days, but there was something special about the city of the Chicago.

When our kids were much younger (around 1 1/2 and 3), we decided that we needed a break. And although we didn’t want to travel too far from home, my loving parents were willing to watch our crazy, sweet kiddos for us to become tourists for a long weekend.

And so, let the memories from Chi-town commence!

Chicago Architecture Tour

One of the tips that we received from friends who had visited Chicago was to go on a First Lady boat cruise through the Chicago Architecture Foundation. This was such a treat! Logan and I got to see some of the very best views that Chicago has to offer all while an educated tour guide gave us the city’s scoop.

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If you are ever in Chicago, I highly recommend purchasing tickets for this tour.

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Head to Wrigleyville, duh!

It is no secret that Logan and I, (especially Logan), love visiting ballparks across America. In addition to Fenway Park, Logan really wanted to see Wrigley Field and so we made his baseball dreams a reality.

We grabbed a drink in Wrigleyville, the area around Wrigley field full of bars, restaurants and endless energy for the Cubs.


It was a surreal experience to see all of the Cubs fans cheering for their home team and joining in on the fun. What an awesome baseball village they have around Wrigley Field!

Girl and the Goat

This restaurant has easily become one of my top two restaurants in the world! Started by a Top Chef contestant who was local to Chicago, this outstanding American cuisine restaurant with eccentric flair was one of the most interesting places we have ever dined.


Girl and the Goat offered family-style outdoor patio seating where everyone dined together around a farmhouse table and it was a blast! From good food to great conversation, we will forever remember our experience here.

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Chicago-style Pizza

Although we aim to follow a semi-healthy lifestyle in our dietary habits, we knew that when in Chicago, you must eat like Chicagoans! And so, we set out to try Giordano’s Pizza, the famous deep-dish pizza that Chicago has made famous.

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We had a bit of a wait to get in, but it was so worth it! I can still taste that pizza pie and its deliciousness! I hardly ate dinner later that day because I was so full from this experience!

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The Bean

The world-famous statue referred to as The Bean, called Cloud Gate, is located in Millennium Park in the Loop area of Chicago. When you’re a tourist in Chicago, you have to get a picture with The Bean! It’s a rite of passage!

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The Signature Room

A final awesome experience we had in Chicago was taking the elevator up to the 95th floor of the John Hancock building – hello, popping ears! The Signature Room experience was such a cool Chicago sightseeing opportunity – especially at night. We waited in line for this amazing experience featuring incredible views of the city. And it was such a special experience that we were so glad we did, together.

Trek Difficulty Level: (1): When we visited Chicago in 2016, we had the pleasure of flying direct from St. Augustine airport (our local airport) to Chicago on Frontier Airlines. It was super close and so super easy. Sad to share that this service has been cancelled for now, but it is still easy to access from JAX with direct flights daily.

Trek Budget: $2500; for a long weekend in Chicago, you could easily find a hotel room, purchase both flights, buy tickets to a Cubs game and enjoy a luxury dinner at Girl and the Goat for under $2500.

3 Trek Must-Dos: 

  • Make reservations for Girl and the Goat. This restaurant is super popular and without a reservation, it is super rare to find an opening to dine there.DSC_0099 (3).jpg
  • Stay at the Gwen Hotel, a luxury boutique hotel. It offered beautiful views, had a cool rooftop bar with a fire pit and was attached to a mall which provided great shopping opportunities.
  • Walk the river! There are beautiful restaurants, shops and bars along the strip of Chicago River. Bring sneakers for sure!

Landon & Griffin’s Trek Tip: N/A

XO, Childless Logan & Meg

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