What are the best ski resorts near Chicago?

The best ski resorts near Chicago for weekend trips include Alpine Valley WI (66 miles), Little Switzerland (67 miles), Cascade Mountain (115 miles).

How far is the closest ski resort from Chicago?

The closest ski resort to Chicago is Alpine Valley WI, approximately 66 miles away (about 1 hour drive).

Can you do a day trip from Chicago to go skiing?

Yes! 2 resorts are within 100 miles of Chicago, making them perfect for day trips: Alpine Valley WI, Little Switzerland.

Weekend Ski Trips from Chicago

8 ski resorts within a 4-hour drive for the 2025-2026 season

Planning a ski weekend from Chicago? We've compiled the best resorts within driving distance, organized by trip type. Whether you want a quick day trip or a full weekend adventure, there's a perfect mountain waiting for you.

🚗 Day Trip Options (Under 2 Hours)

Perfect for a quick getaway - hit the slopes and be home for dinner.

~72 min drive

Alpine Valley WI

66 miles 90 acres

~73 min drive

Little Switzerland

67 miles

🏔️ Weekend Getaways (2-4 Hours)

Worth the extra drive for bigger mountains and more terrain.

~2 hr drive

🎿 Weekend Trip Planning Tips

⏰ Leave Early

Beat traffic by leaving Chicago before 6 AM on Saturday. You'll arrive as lifts open.

🏨 Book Ahead

Weekend lodging fills up fast. Book at least 2 weeks in advance for the best rates.

📦 Pack Smart

Layer clothing, bring snacks, and check resort gear rental availability before you leave.

🌨️ Check Conditions

Monitor snow reports and road conditions.

All Resorts Near Chicago → Other Cities