I originally came to Chicago in my early twenties, planning to stay for about two years. In a very short period of time, I simply fell in love with the city (as well as the man that brought me here). Twenty years later, I am still here, raising my family and calling this splendid place home.

It’s hard to single out just a few “must-do” activities for visitors to this remarkable city, but there are many things to do in Chicago with kids. If pressed, here are my top recommendations for families, both those living here and out-of-town guests:


Among the many tour companies, the Chicago Architectural Foundation is my favorite. Go for their River Cruise…you will not regret it! It’s a fantastic way to learn about the city, its architecture and history. Another fun way to tour the city and cover more of its area are Trolley Tours.

Two great tour alternatives: For a more romantic, but still family appropriate, experience catch a carriage ride in the Gold Coast or Lincoln Park area. They are easy to find on Michigan Avenue, around the Water Tower place.

For families with older kids, Segway Tours are yet another great option. I can’t wait for my kids to get older so we can experience this as a family! The company offers several different tours depending on your preferences, all organized in small intimate groups and led by fun and enthusiastic guides.


In recent history, the Millennium Park has become one of Chicago’s best “must-see” destinations. The park is best known for its Cloud Gate, also known as “the Bean,” a fun place to take family photos. You will see why.

The Crown Fountain is another great attraction. Our kids love taking their shoes off and running around in water and cool mist.

There are great outdoor concerts at the adjoining Jay Pritzker Pavilion, as well as weekly movies in Grant Park. Bordering Millennium Park’s south side is the Chicago Art Museum with many wonderful exhibits, particularly its Impressionist collection.


Your visit to Chicago wouldn’t be complete without experiencing its lakefront! For a unique family experience, pack a picnic lunch and head over to Oak Street Beach where your kids can play in the sand or chase the seagulls while you relax and take in the skyline.

Another great way to experience Chicago’s lakefront is to rent a quadracycle (a bike the whole family can ride together) at near-by Navy Pier (see below) and bike north on the impressive lakefront bike/jogging path, past the North Avenue beach up to the Diversey or Belmont Harbors. You will have great views of the city on your way back. Or, bike south from the Navy Pier past the Shedd Aquarium until you reach the Adler Planetarium. (My personal favorite Chicago skyline view!)


For a birds eye view of the city try “the ledge” at the Willis (formerly Sears) Tower… if you dare! I promise spectacular views and a truly exhilarating experience your kids will talk about for a long time!

Another great place for unforgettable views is the Observation Deck at the Hancock Building. My favorite time to visit is at sunset. Stay for dinner if you can get a table and marvel at the sun’s reflection off of the surrounding buildings, such as Oprah’s residence, and Lake Michigan.


Close to the city center and buzzing with energy is the aforementioned Chicago Navy Pier. It hosts the Chicago Children’s Museum and several exciting attractions such as the giant Ferris Wheel, a carousel and many other exciting rides, as well as a miniature golf course. The pier also serves as a dock to many tour boats offering various lake excursions.

Chicago has two great zoos, but I strongly prefer the smaller Lincoln Park Zoo, which is very close to the downtown area and free of charge. It has an impressive exotic animal collection and there is also a Farm-in-the-Zoo, a carousel (always popular with my children) and a great lagoon where you can rent water bikes.

Just north of the Lincoln Park Zoo, is the Peggy Notebaert Nature Musuem with its wonderful butterfly house your kids will love.


For a culinary experience and a different taste of Chicago’s history, consider taking a Deep-Dish Pizza Tour to experience the food which Chicago is famous for, or, for those with more of sweet tooth, join a fun and delicious Chocolate Tour.


Last but not least, if you are visiting in the summer months, you simply must visit Chicago’s legendary Wrigley Field and “root for the Cubbies” – even if you are not a baseball fan (given that I’m from Europe, even after twenty years, I’m still learning the game!). A great way to further enhance this experience is to take the “L” (Chicago’s famous elevated train) from downtown to Wrigley Area (exit at Addison) instead of a taxi, like all true city-dwelling fans.


The Drake Hotel is close to Oak Street Beach. Palmer House Hilton is within steps of Millennium Park, and Hilton Chicago overlooks Lake Michigan and Grant Park.

This article was originally published by Hilton Mom Voyage.

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