ArcaMax

Even if you are one of those travelers who prefers spontaneity, there are definite pluses to planning ahead, especially when kids are involved.

Sure, if you are driving to the mountains for a ski getaway, you might want to wait to see what conditions are like. But if there has been a lot of snow, you don’t want to arrive without a place to stay.

Sure, you can wait to snag a deal on a last-minute flight, but you don’t want to do that when you need four or five seats. With kids, even if it costs a bit more, book nonstop flights if you can. There is less chance of getting stuck missing a connection or having that connecting flight canceled.

That said, booking a package, including flight, hotel and rental car can save you money, as long as you need those components. If you are considering an all-inclusive, think about whether you will go to the offered activities, use the children’s programs or drink the (complimentary) alcohol.

No worries if you missed the Travel Tuesday deals. With our colleagues at Family Travel Forum we have put together The Best Family Winter Getaways for Ever Budget guaranteed to give your gang plenty of winter wow.

If you are hankering for a cruise, consider that January is the start of Wave Season when you will see some of the best deals of the year, with kids free, upgrades, on board credits and more. It is key that you choose the right cruise line and ship for your family. I’ve met families on board who didn’t realize their kids were too young for the organized children’s programs. This is a good time to work with a travel adviser, especially if you are new to cruises. The Cruise Lines International Association enables you to search for a travel adviser who is a cruise expert based on your ZIP code. You can also follow the cruise lines you would like to sail with on social media and join their loyalty programs.

That’s also the case if you are seeking a hotel or resort deal. Some deals are offered just to loyalty program members, which typically are free to join. Visit a city on a weekend when the business travelers are gone. And don’t let weather deter you.

Chicagoans, for example, don’t let the cold cramp their style. Indulge the foodies in your family with restaurant week Jan.23 to Feb. 8. The Windy City has just been named one of the best places to go in 2026 by Frommer’s. And for the ninth consecutive year, Chicago was recently voted the Best Big City in the U.S. by readers of Conde Nast Traveler. Chicago’s free Lincoln Park Zoo is open for exploration 365 days a year. In the colder months, you can admire majestic polar bears, penguins and snow monkeys as they play outside. Bundle up and take a walk along frozen Lake Michigan on the Lakefront Trail. Pose in Millennium Park at the huge 33-feet-high Cloud Gate sculpture (it weighs 110 tons) affectionately dubbed “The Bean” for its shape. The huge sculpture, one of the world’s largest permanent outdoor art installations, is one of Chicago’s most popular sights. And when you need to get indoors, there are plenty of world-class museums to explore, as well as tasty eats. Have you tried Chicago deep-dish pizza yet?

Come to NYC in January and score 25 percent off hotels during NYC Hotel Week (until Feb. 12). At the same time, with NYC Winter Outing (Jan. 20 to Feb. 12) also includes NYC Restaurant Week with hundreds of restaurants offering specially priced meals starting at $30, NYC Broadway Week with 2-for-1 tickets and NYC Must-See Week with 2-for-1 tickets to attractions, museums, tours and more.

If you want to hit the snow, there are bargains to be had – and lots of festivals celebrating winter. The International Snow Sculpture Championships in Breckenridge, Colorado, (Jan. 24 to Feb. 3) is the place to watch artists from around the world create spectacular huge sculptures from blocks of ice.

Pigeon Forge Winterfest (until Feb. 15, 2026), near Dollywood in Tennessee, boasts six million lights illuminating the city, a drive-through light show, music, holiday performances and winter shopping events. It’s a great time to visit Dollywood and Smoky Mountains National Park, the country’s most visited, in the off-season.

Opt for smaller snow resorts like The Maine Highlands, emerging as one of New England’s most family-friendly and budget-friendly winter destinations. The Gems Discount Cards ($49.99) offer two visits each to 10 smaller Colorado resorts with deeply discounted lift ticket prices. For example, you can ski or ride at Cooper for just $44 Monday through Friday.

Colorado, like other states, including Utah, Vermont and New York, offers a Ski Passport for kids (in Colorado it’s available for kids K-6, offering 76 days of skiing and rentals for $72, or less. You don’t need to live in the state to get a passport, but each one is slightly different.

There are also kids-free deals, even at major resorts. For example, rent kids equipment (ages 7 to 12) at Four Mountain Sports in Aspen Snowmass and kids get complimentary lift tickets for the same number of days.

Nowhere has more free museums and sites than Washington, D.C., where there are 100+ free things to do. Visit the National Mall, the Smithsonian museums, the Library of Congress, the largest in the world and see the Declaration of Independence and the Constitution in the National Archives. You can even take a guided walking tour with DC by Foot.

Isn’t it time to get going?

========

(For more Taking the Kids, visit www.takingthekids.com and also follow TakingTheKids on Twitter, Facebook and Instagram where Eileen Ogintz welcomes your questions and comments. The fourth edition of The Kid’s Guide to New York City and the third edition of The Kid’s Guide to Washington D.C. are the latest in a series of 14 books for kid travelers published by Eileen.)

©2026 Eileen Ogintz. Distributed by Tribune Content Agency, LLC.

(c) 2026 DISTRIBUTED BY TRIBUNE MEDIA SERVICES, INC.