Bundle Up and Get Ready for Winter Fun! Checkexpress

Bundle Up and Get Ready for Winter Fun!

While living in the Midwest, cold winters are inevitable! If you sit around and wait for summer, it will only make the winter season feel that much longer. Whether you enjoy the chilled temperatures from the inside or dress up for those extra crisp days, our 2019 guide for winter fun will have you enjoying the season…

Ice Skating and Family Fun

Millennium Park McCormick Tribune Ice Rink
Chicago, IL
Take a spin on the ice with the family, out with friends, or for date night! Millennium Park is the perfect location central to restaurants, theaters, coffee shops and more! Skating is FREE and open to the public. Skate rentals are available.

Skating in the Park
Rosemont, IL
Enjoy an early dinner at the Entertainment District in Rosemont before heading to open skate in the park! Open skate is available every Sunday from 4pm – 10pm. The Entertainment District is located only 1 mile from the Fashion Outlets of Chicago.

Skatium Ice Arena 
Skokie, IL
If ice-skating outdoors just isn’t your thing be sure to check out Skatium Ice Arena in Skokie. Host a birthday party or work meeting with party room rentals this winter!

Garfield Park Conservatory East Garfield Park 
Chicago, IL
For families who really want to escape the cold and explore the botanical themed gardens the Garfield Park Conservatory is the perfect spot! Enjoy and learn about the gorgeous green acres of the fern house, desert house, palm house and more. Indoor gardens everyone can enjoy!

Places to Ski

Villa Olivia 
Bartlett, IL
Just a short drive from anywhere in the Chicagoland area, Villa Olivia offers winter sports for the entire family. Enjoy downhill skiing, snowboarding, and snow tubing. Lessons are available for all levels!

Norge Ski Club 
Fox River Grove, IL
Ski Jump Tournament January 26-27, 2019
A weekend of fun for the entire family! Enjoy ski jumpers from around the world while you enjoy brats, hot dogs, pizza, and drinks for the adults. No snow, no problem! Norge Ski Club makes their own!

Wilmot Mountain Ski Resort 
Wilmot, WI
Newly remodeled Wilmot offers local lodging, dining, rentals, and lessons for all levels. Wilmot Mountain is right across the Illinois border.

Cascade Mountain 
Portage, WI
A longer drive from northern Chicago suburbs than our other recommended destinations, but well worth the drive for a long, weekend stay. Cascade is larger than the other ski resorts mentioned with scenic views, a wide variety of trails, and conveniently placed ski lifts granting you access to a variety of trails.

The Best of the Local Winter Festivals

Chicago Auto Show
Chicago, IL
February 9 -18, 2019
Kick into high gear with the Chicago Auto Show! It’s the nation’s largest and longest running auto show and will be taking place at McCormick Place. Experience the newest and latest designs in the auto industry!  Be sure to check out special days at the auto show: Women’s Day, Food Drive, Family Day and more!

The Orchid Show
Glencoe, IL
A family-friendly event showcasing a variety of orchids displayed under magnificent lights in greenhouses and galleries. Treat yourself to a relaxing day while you enjoy live music or a weekend brunch with a view at the Garden View Café.

Before you go…

Prices, event dates, and hours vary so be sure to check days and hours on their website. You’ll also find up-to-date information on upcoming events and special deals!

Need cash? Stop by one of our 9 Checkexpress locations around Chicagoland!

Visit our social media pages to share your family’s favorite winter activity!


Due to the COVID-19 outbreak, store hours and/or services may change unexpectedly.

Please call first to confirm store hours and availability of services for the day.

Thank you and stay safe.