If you’re looking for a deep-dish pizza, world-class hockey, or a walk through Millennium Park, we can help you see—and eat—it all with a Chicago vacation package. There’s always something to do here in the crown jewel of Illinois, from a walk on Navy Pier to the gorgeous boutiques on the Magnificent Mile. Pardon our pun, but we’re sure “The Windy City” will “blow” you away!
When is the best time to go? You will be less limited with a baby or a toddler because they don’t yet go to school, allowing you to plan a trip in September or early May when places are less crowded and room rates are lower. If you have older children that are in school, you will need to get away during their school holidays like spring break and summer. During the summer season, most beach destinations are quite crowded while cities tent to be emptier and a good choice as vacations for kids. If you have a teenager who is learning about the U.S. history, take her to Washington D.C. and spend a few days at the Smithsonian Museums.
Boston has it all—the culture, the fantastic city parks, and a relaxed pace you might not expect in a city of its size. Baseball fanatics, young and not so young, will love Fenway Park, home of the Red Sox. You can take a guided tour, watch a game, and soak up some sporting history. Also check out the giant ocean tank at the New England Aquarium and board a Boston Duck Tour to be transported around this beautiful city on land and water.
WOW AIR: WOW Air as grown at a staggering rate since it first began flying from the USA in 2015. It now flies from 13 U.S. airports, including just-launched service from airports in Cleveland, Cincinnati, Detroit and St. Louis. All of WOW’s U.S. flights are to its hub near Reykjavik, where connections are available to more than 20 European destinations. Flights from Iceland to India will provide a new option starting in December 2018. Jeremy Dwyer-Lindgren, special to USA TODAY
For accommodations, look to save by staying in a Tahitian Guesthouse, or pension. These family-operated lodgings provide a more authentic glimpse into Tahitian culture without an expensive price tag. Many prepare meals in the house kitchen and offer excursions, like pearl diving with a local guide. With only a few rooms or bungalows onsite, you get a more intimate (and less expensive) experience than you’ll find at larger resorts.
Where do we go on the East Coast? During the summer months, visit the scenic coast of Maine, stay at a family resort in Vermont, take a trip to New Hampshire, relax on the beach in Cape Cod and enjoy other family vacation spots. Visit the museums of New York, Boston and Philadelphia, dine a family-friendly restaurants, and watch outdoor theater performances with older children. In the winter, plan a ski trip that will let your kids learn how to downhill ski, cross-country ski or snowboards at a New England mountain resort such as Stowe, Killington or Sugarbush.
When you're looking for the best family vacations in the Caribbean, there's no place better than Beaches, where our all-inclusive family vacations offer something for everyone, from unlimited land and water sports to gourmet dining choices for every palate. Grown-ups will enjoy up to 13 bars serving premium brand liquors and varietals Mondavi wine. Kids and teens will get a variety of fun activities, with sprawling water parks, Xbox Play Lounge and the Caribbean Adventure with Sesame Street®. Best of all, everything is included at our family all-inclusive resorts.
“I cannot speak highly enough of how well-organized this tour was. Everything matched up to the tour description and our tour guide Nick and driver Tony made the day absolutely fantastic. Nick was very informative about all landmarks and aspects of the DC area and was happy to answer all questions that came his way. Highly recommended to anyone looking to experience the monuments and history of DC!” — TripAdvisor Reviewer

Weekend getaways – leaving Friday and returning Sunday – are awfully convenient if you work a Monday through Friday job, but you can expect to pay handsomely. According to Expedia, which releases an annual Travel Trends White Paper, you’re likely to pay 20% less for a flight that departs on Thursday and returns on Monday than one that departs on Friday and returns Sunday.
Located on the southern edge of Lake Erie is chilled-out Sandusky. This place is home to the Cedar Point amusement park, which draws rollercoaster-crazy visitors each year. It’s mostly for the thrill-seekers, but there are also gentler options available for younger children. Alternatively, you can take jet skis out on the lake or enjoy a stroll with stunning views along the Sandusky Bay Pathway.

CheapOair makes it easy to find and book travel packages at great prices. Now you can save even more by booking your flight, hotel, and car rental together. CheapOair works closely with top travel brands to ensure that you get the best vacation deals possible. We offer cheap vacations & packages to the most sought after destinations around the globe. From all-inclusive vacations to kid friendly destinations, romantic and leisure travel, to name a few.
×