Chicago Family Vacations

Easily accessed from both coasts (and from most major international cities), Chicago attracts families looking for phenomenal food, art, architecture and kid-friendly fun in a historic yet urban setting. Spend leisurely mornings in some of the world’s best museums, take a windy walk along Lake Michigan, cheer on the home teams and dig into deep dish pizza. Don’t miss the chance to take an architecture tour by boat or trolley, and then admire the unique skyline from Navy Pier while riding the Ferris wheel. Book a downtown high-rise hotel for easy access to all the kid-friendly attractions, stunning views and luxury amenities that make a getaway to Chicago feel like a true vacation.

Our Happy Travelers

"We have only good things to say about our entire trip and the planning process. You are a dream to work with! I especially appreciated how you narrowed down my options for each decision, so I wouldn't be overwhelmed. I haven't worked with a travel agent before, but you really surpassed my expectations. We will call you first the next time we travel!"

–Caldeira Family Trip

"The hotel you found and booked for us could be the nicest hotel we have ever stayed... and we have stayed at some really, really nice 5 star hotels."

–Wadsworth Family Trip

“I have been blown away with the services you provide. I first contacted Barbara last summer on a recommendation to Ciao Bambino from a friend. I wasn't sure what to expect as I had not used this type of service before. We were beyond impressed with everything Barbara set up for our family.”

–Detter Family Trip

"I couldn't be happier with my experience. Just talking with Cary gave me a baseline foundation to build on - one that I didn't have time to get from reading a guidebook and distilling it. I am not sure how I would have gotten this trip together without her help. I will definitely get in touch before our next trip!"

–Marks Family Trip

"I will always remember Ciao Bambino. Our advisor was wonderful to work with. I would recommend Ciao Bambino in a blink to others."

–Frus Family Trip

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Chicago Family Vacations

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Our Happy Travelers

"The hotel you found and booked for us could be the nicest hotel we have ever stayed... and we have stayed at some really, really nice 5 star hotels."

“I have been blown away with the services you provide. I first contacted Barbara last summer on a recommendation to Ciao Bambino from a friend. I wasn't sure what to expect as I had not used this type of service before. We were beyond impressed with everything Barbara set up for our family.”

"I will always remember Ciao Bambino. Our advisor was wonderful to work with. I would recommend Ciao Bambino in a blink to others."

Build a Lifetime of Memories

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Washington, D.C.

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Chicago Family Vacations

USA

USA

Top Articles About Chicago with Kids

Midwest College Tour & Vacation Itinerary

7 Hidden Gems for Families in Chicago

12 Kid-Friendly Urban Hotels with Fabulous Pools

72 Hours in Chicago with Kids

Our Happy Travelers

"The hotel you found and booked for us could be the nicest hotel we have ever stayed... and we have stayed at some really, really nice 5 star hotels."

“I have been blown away with the services you provide. I first contacted Barbara last summer on a recommendation to Ciao Bambino from a friend. I wasn't sure what to expect as I had not used this type of service before. We were beyond impressed with everything Barbara set up for our family.”

"I will always remember Ciao Bambino. Our advisor was wonderful to work with. I would recommend Ciao Bambino in a blink to others."

Build a Lifetime of Memories

New York City

Philadelphia

Washington, D.C.

Family-Friendly Sample Itineraries

Portugal

Scotland

Costa Rica

England

Spain

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