Chicago 15 Year Old Adventure

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Celebrating our Kids with their Very Own Adventures

We love to celebrate the various milestones of our kids. They each look forward to choosing their own adventure with mom and dad at 10, 15, and 20. Sometimes we throw in others, too, if the opportunity presents itself. Family adventures are always going to happen, but we like to celebrate the uniqueness of each kid and enjoy the time relating to them individually. Rowan chose Chicago for his 15 year old adventure!


The jump from age 10 to age 15 is enormous. So much happens during those years and it gives us as parents a good launchpad to connecting with our teens. A successful adventure with a teen surprisingly looks pretty similar to one as a 10 year old.  I can’t emphasize enough how far it goes to reaching a child’s heart by being interested in what he/she is interested in. For our family, these adventures are about going and doing what that child wants to do.


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I know we all live on a budget, but I implore you to splurge in a way that makes your kid feel special. After all, these are memories you are creating, not just something that will be thrown away after a few months. We bought good seats to watch Ro’s favorite MLB team in the most iconic ballpark ever and a fun ride on the Red Line to the game with all the other Cubs fans! Rowan is a foodie with an extremely mature palate so we ate our way through the city at restaurants he requested. Of course one of his favorites was the hot dog at Wrigley-gotta get that Chicago dog! We had a swing and a miss with a restaurant we TRIED for 2 hours to get in to and ended up with a late night stop at Portillo’s for an Italian beef sandwich. We walked along the lakefront to get a glimpse of all the sailboats, saw Millennium Park, finally we made a stop at the Art Insitute.


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One of the best ways to see Chicago is from the riverfront and from ON the river. If you spend any time walking downtown in the loop you will cross over one of the many bridges. The city has done so much to clean up the riverfront walkways, so when the weather is pleasant you will find a lot of people down there enjoying the restaurants, bars, and boat life. The other splurge we indulged in was the sunset evening cruise on the architectural boat tour. Don’t miss this!!! Learning about the different buildings in the city from the different eras is super interesting and you get to do it all while cruising down the river. Spend the extra few bucks to do it as the sun begins to go down so you can see the changes from light to dark. it is an unforgettable experience.


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The other best way to really see the city is from the top. There are two locations you can do this from: The Hancock building on Michigan Ave and Willis Tower on State St. Either way, you will get fantastic views of the lake and the city from up above and you can’t help but feel so small up there.


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There are a host of other activities to do as adults or with children. We focused on what Rowan wanted to do for the weekend. Here is a list of other ideas for your time in the Windy City.

Shopping on Michigan Ave for the popular retail stores or look in the Wicker Park area for more boutique shopping.

♠ Every museum is awesome: The Field Museum to see Sue the dinosaur, The Museum of Science & Industry, The Art Insitute of Chicago, the Adler Planetarium, the Chicago Children’s Museum, the  Chicago Sports Museum, the Richard H. Driehaus Musuem, Frank Lloyd Wright’s Robie House and more.

♠ Chicago Bears Soldier Field, The United Center, Wrigley Field sports venues

♠ Chicago pizza options include Lou Malnati’s, Pizzeria Uno, Pizzeria Due, Giordano’s, and Gino’s East to name a few. That deep dish pizza is special! Every Chicagoan has their favorite spot-mine is definitely Lou Malnati’s!

Navy Pier is great for kids with all kinds of arcades, outside games, beer gardens for parents while kids play, and the big Ferris wheel.

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