Why you’ll love it: It’s a city with a sandy beach right downtown! How fun is that? Plus there are scenic riverboat rides, the Shedd Aquarium, the Field Museum of science, Lincoln Park and the zoo, the Museum of Science and Industry, and a giant Ferris wheel at Navy Pier. Oh, and pizza, lots and lots of cheesy, stringy, deep-dish pies perfect for family dining.

The best family vacations become the stuff of legend, inspiring the stories you and your relatives repeat and reminisce over for years. That’s not to say mishaps don’t happen: National Lampoon has made five Vacation films based on that very pretense. The stakes can sometimes feel impossibly high to plan the perfect vacation that everyone will love. (And that’s without factoring in a budget.) Travel + Leisure’s writers and editors know how stressful planning family vacations can be, but also how stress-free they should be. With a discerning eye for value, multigenerational fun, and simplicity, they can help reduce the hassle and maximize the memories.


No. 8. Hollywood Beach – Hollywood, Fla. Hollywood Beach is well known as a family-friendly place due to the calm water, available bathroom facilities, live entertainment and the nearby restaurants across the large Boardwalk. “Hollywood Beach is clean and beautiful. The boardwalk is great for biking, walking, enjoying a meal or drink at a restaurant. Many places to stay right on the boardwalk,” added a TripAdvisor user. • Beachfront bargain hotel nearby: Hyde Resort & Residences, from $293 per night on TripAdvisor • Great airfare found on TripAdvisor: As low as $77 round-trip from ORD (Chicago) to MIA (Miami) TripAdvisor
Why you’ll love it: Known for its natural beauty, sustainability, and outdoor activities, Portland is a favorite option for affordable family vacations. It’s a great destination for teens who will enjoy biking around the city like a local or taking in the sites on the great public transportation system, including a cool funicular (and a pass is only $5). There are hip vintage spots and multiple food truck parks where they can try food from around the globe without high restaurant prices. Take in the views of the city and the 500 plant varieties at the International Rose Test Garden.
The Magdalena Grand Beach Resort, set among a virgin mangrove forest and lush tropical vegetation, offers the ultimate escape to paradise at a more affordable price. It includes lots of family-friendly features, like three large swimming pools and a free kids’ club with the chance to learn about Tobago’s green, leatherback and hawksbill turtles. A free shuttle will bring you to popular Pigeon Point beach, while the complimentary buffet breakfast offers lots of tasty hot items, including an omelet station. Rooms feature ocean view balconies and even marble baths, along with numerous dining and drinking options, including a piano bar and a coffee shop.
*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.
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