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Cloud Gate, also known as the Bean, is located in Millennium Park.

Although Chicago is one of the top destinations for business travel in the United States, it is also a wonderful spot for family vacations. The big city vibe is coupled with gorgeous city scapes in an architectural paradise as well as breathtaking views of bright blue Lake Michigan. For such a gorgeous city, it lacks the over-the-top crowds found in places like New York and Los Angeles.

Where to Eat

There’s no way around it—you must have deep-dish pizza during your trip to the Windy City. The best of the best is Lou Malnati’s. With various locations around Downtown, the pizzeria serves reasonably priced pizzas, pastas, salads, appetizers and a plethora of desserts including peach cobbler, a chocolate chip cookie pizza and tiramisu. The wait for a table can get lengthy, but they let you order your pizza while you wait so it is ready around the time you get a table—definitely a great timesaver when traveling with little ones.

Another staple of Chicago cuisine is the hotdog. In the West Loop area on Lake Street, you will find Fast Track. Their Vienna all-beef dogs come with onions, tomatoes, relish, mustard, peppers and a poppy-seed bun. They also have charbroiled, cheddar and foot-long hotdogs.

Lou Malnati's makes some famous Chicago deep-dish pizza.

Where to Play

Heading east, you can’t miss the Navy Pier, a fun pastime for family vacations. Walking along the pier in the sunshine with the blue water around you and Chicago’s skyscrapers behind you, you can’t help but feel content. Take a ride on the massive Ferris wheel with your toddler for some spectacular views of the lake the city then grab a crepe from the nearby crepe stand. Inside the main pavilion on the pier, do some souvenir shopping or play games like mini golf. There is also a Children’s Museum where kids can dig up dinosaur bones, dress up as a firefighter to put out a fire and construct a skyscraper.

Shoreline Sightseeing offers a boat tour on the river that leaves from a dock near the pier as well. You might think toddlers would be too young to enjoy the informative cruise focused on architecture and the city’s history, but the small children on our tour had just as much fun enjoying the sunshine and the gentle breeze as they took in the sights and sounds of the city. Traveling on three branches of the Chicago River, it is a great way to orient yourself and see a whole lot.

The Navy Pier is home to a very large Ferris wheel.

Once you disembark, head south to Millennium Park. The park is home to various pieces of artfully crafted landscape features and architectural art forms. It is a great place to enjoy picnics while on family vacations. It is also home to Cloud Gate, more commonly known as the Bean. This outdoor installation, made of stainless steel, reflects the skyline and the clouds above. Toddlers especially will love seeing their own reflection in the structure and exploring the concave space underneath.

Where to Stay

Located directly to the east of the Navy Pier on State Street, Hotel Palomar offers an exciting hotel experience for families. Toddlers are greeted with a welcome gift, a pet fish in your room and an animal print robe to wear during your stay. The hotel also provides outlet covers, toilet latches and nightlights to make your stay as safe as it is fun.

Shoreline Sightseeing takes visitors on architecture tours of the Chicago River.

If you’re looking to cut down on costs, consider staying at Chicago’s Hosteling International location. Offering cheaper private rooms than a hotel and free breakfast, you will be free to spend your money on your activities instead of your accommodations. You also can rent a bus in Chicago at an affordable price. Although a hostel may not seem ideal when traveling with toddlers, Hosteling International offers private rooms that are perfect for families. It is also located near the Loop so you won’t be far from the action.

For more information visit:
Lou Malnati’s
Fast Track
Navy Pier
Children’s Museum
Shoreline Sightseeing
Millennium Park
Hotel Palomar

Ashley Ryan

Author Ashley Ryan

Ashley Ryan is a southern California native with a background in journalism and anthropology. She loves learning about other cultures and combines her passions for traveling, writing and photography in her professional work. To learn more or get in touch, visit

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