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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.

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Experience the Best of Chicago with Kids

Let Ciao Bambino! Plan Your Dream Trip

Our expert Family Travel Advisors are passionate about exploring the world with children — and empowering you to do the same. From handpicked accommodations to insider experiences, we can craft a custom vacation that’s uniquely suited to your family’s needs. Click to get started!

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Travel Blog

Top Articles About Chicago with Kids

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Traveling with Tweens and Teens

How to Turn a College Tour Into a Vacation: Midwest Edition

By Amy Andrews
City Breaks

7 Hidden Gems for Families in Chicago

By Nicole Wiltrout
Accommodation Review

12 Kid-Friendly Urban Hotels with Fabulous Pools

By CB Staff
City Breaks

72 Hours in Chicago with Kids

By Dana Rebmann
Accommodation Review

Family-Friendly Hotel Bliss at The Langham, Chicago

By Amie O'Shaughnessy
Accommodation Review

The Peninsula Chicago Takes Family Amenities to a New Level

By Amie O'Shaughnessy
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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Coronavirus Update

This is a challenging time for our clients given the uncertainty around the spread of coronavirus, particularly for those with near-term travel plans in impacted areas. We’re working with our suppliers on being flexible with their booking conditions, and enabling families to postpone travel to a later date without a penalty, when possible. Likewise, given the unpredictability around destinations that may be impacted in the future, we’re helping clients planning new trips and understand ways that they can protect themselves until the situation improves. We are ready to help our clients work through questions and concerns.

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Happy Thanksgiving!

Our offices are closed for the holiday. We will respond to your request on Monday, November 28th. If you are a Ciao Bambino client experiencing an emergency while traveling, please leave a voicemail on
(855) 589-8865.