A Weekend With Little Ones In The Windy City

By Stephanie Trovato

Chicago is a huge and diverse city to visit. Incredible food, architecture, and plenty of world-class attractions and museums — it’s the perfect destination for a family trip.

Get ready to explore the Windy City on a kid-friendly weekend in Chicago. This Chicago itinerary is packed with fun for everyone.



Your first day in any new city should no doubt include sightseeing — and this Chicago itinerary is no exception.

Riverwalk: The Riverwalk in Chicago is one of the most well-developed and beautiful urban trails, allowing you to take in the sights, smells, and skyline. Watch the hustle and bustle of the morning commute, or visit during the evening hours for an array of restaurants to choose from.

Millennium Park: Once you reach the end of the Riverwalk, enter Millennium Park. With a live music amphitheater, picnic-friendly field, the Crown Fountain and reflecting pool, endless gardens, rotating art exhibits, and a busy calendar of public events all year round, you won’t have to worry about your family getting bored.

The Bean: Capture those memories with selfies by The Bean, Chicago’s most-photographed monument. Standing 30 feet tall with a mirror-like finish, your family will love checking out their silly faces in the reflection.



Soak in local history and culture on your weekend in Chicago with a visit to a few well-known landmarks.

The Field Museum: Marvel at one of the most feared predators of the Cretaceous period — the “king” of the dinosaurs. The touchable T. rex cast reaches 122 feet across and 28 feet tall at the head and truly conveys the sheer size of this prehistoric creature.

Chicago Food Tours: Dive into the delicacies of Chicago eating. Picky eaters? No problem. From Chicago-style hot dogs to deep-dish pizza, there’s something for everyone in your family to enjoy.

Skydeck: Experience new heights with an adventure on The Ledge. See the city from the 103rd floor of Willis Tower as you’re tilted into a bird’s-eye view that offers sky-high memories.

Maggie Daley Park: Back on the ground, enjoy the sunshine and fresh air at Maggie Daley Park. Parents can sip a coffee from the Rink Café while the kiddos burn some energy on the climbing wall or running around the play garden.


From sea to space, be sure to include these fun-filled educational spots in your Chicago itinerary.

Shedd Aquarium: Opened in 1930, it was once known as the largest aquarium in the world with 5 million gallons of water. The entire family can search for their favorite underwater creature with over 32,000 animals to see.

Adler Planetarium: Inspire your future astronauts with a visit to this historic planetarium. Spend the afternoon learning about the Ring Nebula and immersing yourself in a high-tech star show, then stop at the cafeteria for lunch.

Museum of Science & Industry: If space isn’t your thing, take a drive to the Museum of Science and Industry for a hands-on tour of the most famous inventions in the world.