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Best Winter Road Trip Destinations Near Chicago

By Jessica Cage

Winter is rolling in, and for your family that will mean winter vacations. Children will get, on average, about three weeks out of school for winter vacation. What will you do for those three weeks? You want to avoid having your children sitting in front of the television the entire time playing video games and watching cartoons. Take the initiative to avoid zombie children this winter by planning a trip or two. There are numerous options for a quick family trip within driving distance of Chicago. Plan ahead and create a great winter vacation for your family.

Wilderness Resort

Wilderness Resort
511 E. Adams St.
Wisconsin Dells, WI 53965
(608) 253-9729

Just over three hours northwest of Chicago is the Wilderness Resort of Wisconsin Dells. There you will find indoor water parks and other attractions to entertain you and your family. Enjoy a game of laser tag or hop on the bumper boats. For the family who really loves adventure, there is the sky ropes course, a course made of ropes that sits 30 feet above the arcade at the Wilderness Resort. This is compared to the thrill of zip lining and is a great alternative for the winter months. And don't forget the WildKids Club where parents and children can take part in games and crafts like Stuff-A-Monty, a furry pal that you can create and take home with you as a memento of the fun times you had.

Related: Best Photographers For Kids Near Lincoln Square

Chestnut Mountain

Chestnut Mountain Resort
8700 W. Chestnut Road
Galena, IL 61036
(800) 798-0098

For skiing and snowboarding, visit Chestnut Mountain Resort. Located three hours west of Chicago and right along the Mississippi River, Chestnut Mountain Resort offers an awesome winter experience for the entire family. Ski season is open from Thanksgiving to St. Patrick's day. Enjoy a seven-acre terrain park with 19 ski and snowboarding trails. Also, give the Farside a try. The Farside is the largest park of its kind with 25 rails for the family to try ranging from novice to expert levels. Lessons are offered for beginners. When you are done with the winter fun outdoors, come inside and relax in your choice of pool, sauna or jacuzzi.

Grizzly Jack's

Grizzly Jack's Grand Bear Resort
2643 Illinois Route 178
Utica, IL 61373
(866) 399-3866

For summer fun during the winter months, Grizzly Jack's Grand Bear Resort is the place to be. Located 90 minutes southwest of Chicago, Grizzly Jack's offers summer fun all year long with its indoor amusement park. The Enchanted Forest is a 36,000-square-foot playhouse that offers amusement rides, miniature golf, an arcade and Jack's Place Restaurant with its signature pizzas. When you are done there, take a stroll over to Grand Bear Falls, the 24,000-square-foot water park which offers water slides, a lazy river and much more.

Safari Land

Safari Land
701 W. North Ave.
Villa Park, IL 60181
(630) 530-4649

Safari Land offers indoor family fun close to home. Plan to visit Safari Land for a quick day trip for you and your family. All it takes is a half-hour drive and you will be able to enjoy tons of fun, from go-carts to bowling and even the Lion's Den, a soft play area for the smaller members of the family. Try out the Max Flight Simulator or the Tiger Terror Roller Coaster before heading over the the Atlantis Restaurant. Safari Land offers an all-around day of fun for you and your family. Visit the website for pricing and special group rates.

Ben's Christmas Tree Farm

Ben's Christmas Tree Farm
7719 Ryan Road
Harvard, IL 60033
(630) 279-0216

Nothing says winter vacation like picking out a Christmas tree. Bring the family together not only to decorate for the holidays but also to choose the tree that will light up your home this season. Take a 90-minute drive to arrive at Ben's Christmas Tree Farm where you will find thousands of trees that range in categories from red pine to white spruce. While you are there, enjoy a free horse-drawn wagon ride, a visit with Santa and pet some farm animals. Grab a cup of hot cocoa or coffee as you choose the tree that is right for your family.

Related: Free & Cheap Winter Break Activities In Chicago

Jessica Cage is a freelance writer from Chicago. Her work can be found at


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