[category]
[title]
At Time Out, we’re constantly refreshing our rankings to ensure we’re championing Chicago’s absolute best—not just recycling outdated favorites. This month, we revisited our guide to Midwest family winter getaways and decided it was time for some big changes.
In addition to scouting fresh destinations, we’ve reshuffled our rankings to reflect shifting travel trends and recent local developments. Based on our latest reporting, Holland, MI, has officially claimed the No. 1 spot as the ultimate winter escape for Chicagoland families.
RECOMMENDED: The best kid-friendly restaurants in Chicago
Blending small-town charm with cozy, kid-friendly adventures, Holland is the quintessential winter getaway for families. Spend your days sledding, admiring frozen windmills or bravely enduring the elements before retreating downtown to thaw out. When the summer crowds vanish and Lake Michigan transforms into a living snowglobe, the city’s charm truly shines. Wander through local favorites like the Apothecary Gift Shop to snag whimsical treasures, then take advantage of the quiet streets and affordable seasonal lodging. It’s a peaceful escape that stays warm long after the sun goes down.
The perks don’t stop at the city limits, either. The equally enchanting town of Saugatuck is just a 20-minute drive from Holland. There’s no shortage of wintry activities in the captivating locale: Catch some air sledding at Mount Baldhead or Oval Beach, or strap on some snowshoes for a trek through the serene Saugatuck Dunes State Park.
When planning your next family getaway, setting your sights on Michigan is a surefire way to guarantee a memorable weekend. Looking for even more inspiration? Check out our full list of 23 other winter destinations, all within an easy drive of Chicago.