(312) 344-3656 phone
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Family Travel

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Creating lasting family memories, one vacation at a time
Imagine being able to get away with your family without the stress of trying to plan a vacation that fits everyone's needs. Now, imagine being able to go where you want to go, and see what you want to see with the ones you love, even on a limited budget. We can make your family's vacation dreams a reality. Our knowledgeable travel consultants specialize in family travel and will make sure that your family gets the most out of every special vacation moment. Whether you're traveling with your infants, toddlers, teenagers, grandparents or a combination of all of them, we can help direct you to the best location, resort or cruise that fits into your budget.

Want to take an action-packed cruise to the Caribbean? We have cruise experts and know which ships have the best amenities and activities for children of all ages and can match you with the perfect cruise line.

Interested in sharing the cultural experience of Europe with your family? We'll coordinate everything from air transportation, to hotel stays, to sightseeing tours and dining arrangements. Or if kicking back on a white sandy beach is more your style, we can help you choose the best destination and family-friendly resort.

We have access to the best deals and exclusive promotions, so you won't have to empty your wallet in order to keep everyone in your family happy.

Call us today and we'll help you fill those vacation photo albums with special memories your children will always cherish.


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(312) 344-3656 Phone

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Effective September 1, 2022 late fees will be increased to $25 per person, per occurrence. ​

​Pineapple Dream Vacations, Inc. | (312) 344-3656
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