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3 Days in Chicago for Families

Organisiert von Lori Zainowho frequently visits the Windy City (her hometown) with her toddler in tow.

Growing up in Chicago was a whirlwind of culture and fun—visiting museums, boating on Lake Michigan, and feeling my stomach drop in the elevator to the 360 Chicago Observation Deck on the 94th floor of the John Hancock Building.

These days, I relish taking my toddler to partake in everything I loved to do while growing up in the Windy City, especially watching his face delight in joy after biting into a delicious slice of deep-dish Chicago pizza. As he grows up, I can’t wait to take him to ride the Ferris wheel at Navy Pier and admire Sue, the giant T-Rex skeleton at the Field Museum. Here are the best things to do on a family visit to Chicago.

Bundle up in winter when it gets extremely cold in the Windy City.

If you only have time for one thing, make it a boat cruise on Lake Michigan.


Day 1

Chicago has a lot of ground to cover, so start with a hop-on, hop-off bus tour. This way, you’ll see all the sites without the kids getting overly tired from too much walking. Get on or off the bus whenever you want, stopping to check out attractions like Navy Pier (don’t forget to ride the Ferris Wheel) or the Buckingham Fountain, which lights up with colors on the hour.

Hop off at the Field Museum, where the whole family can enjoy viewing dinosaur skeletons, interactive ancient Egypt exhibits, and more.

Day 2

Feel Chicago’s bustling, busy energy by walking around the city streets, looking up to view the towering skyscrapers and enjoying skyline views from Millennium Park. Children will love seeing their reflection in the Cloud Gate (the Bean) sculpture, a mirrored piece of artwork.

Once the family is tired from walking, get out onto the water with a boat cruise on Lake Michigan. You’ll be able to get the perfect family photo from the boat with Chicago’s beautiful skyline in the background. Alternatively, teens may appreciate an architectural boat ride along the Chicago River.

Day 3

Forget trying to make your children eat veggies; let them indulge in some famous Chicago deep-dish pizza. Visit restaurants like Lou Malnati's Pizzeria or Gino’s East to try it, or consider a pizza tour to sample Chicago ‘za at various spots.

Grab a taxi to the nearby suburb of Schaumburg to take the family to LEGOLAND® Discovery Center. Although there are LEGOLAND parks worldwide, this particular one offers a mini-replica of famous Chicago landmarks made from millions of LEGO® pieces that the whole family will appreciate.

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