The Benfields are in the Windy City this weekend for some family time. Actually, I have a wedding at the Chicago Athletic Association, but we came a little early to show Scout that this city is more than just an airport. (Scout has been to O’Hare around ten times already!)

During this trip, and most of our trips, I plan the food and Tyler plans the activities. For our family weekend in Chicago, we hit up some of the classics, as you’ll see in our gallery of images below.

These scenic shots are from the 103 floor of the Willis Tower (it used to be called the Sears Tower if you weren’t sure what I was talking about). We went at sunset and the lighting was surreal!

We stayed at the Chicago Athletic Association (a really cool hotel on Michigan Ave with old vibes!) so we were right across the street from Millennium Park. Because we talked to Scout about “the bean” all the way here so we had to show her the attraction in person. You know how sometimes something is cool to parents but kids don’t appreciate it? Well, this was NOT the case here… Scout LOVED the bean!

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Obviously we took a family selfie!

For brunch the following morning, we met Tyler’s college friend Bosé (“bossy”) and Scout made a new best friend almost instantly. The food at Beatrix was great too! We recommend the french toast.

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The french toast put Scout into the best mood, so we played in our little booth.

Chicago is a great city to visit if you’re alcohol free! We have had mocktails and AF wine every place we’ve dined!

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We visited the Sky Deck at Willis Tower. The express elevator was closed so it took a little longer to get up to the top; however, it was worth it because we got to the top at sunset. Scout had no issue walking out and standing on the clear platform 103 stories up in the air.

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On the day of the wedding, I had the morning free so we popped over to the Shedd Aquarium to see fish. Scout has been to a few aquariums now and is always excited to see the fish, turtles, sharks, and seahorses. Shedd also had ducks so Scout would add “and animals” when I ask if she liked seeing the fish. HAHAHA, that kid.

I want to end with these two shots, both taken from atop Willis tower. I am drawn to these two images because of their soft light. Sunset doesn’t have to be harsh or bold or silhouette. These two images almost feel pastel in quality. What do you think?

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Overall, Chicago showed our family some really fun things this weekend. From kid-friendly attractions like the Shedd Aquarium, Sky Deck at Willis tower, to hip restaurants that welcomed children. Our favorites of the trip were Hampton Social, Beatrix (which had a delicious alcohol-free margarita), and Cindy’s Rooftop at the Chicago Athletic Association.

Talk to you soon,
Dale