Well the weather outside is actually less than frightful, and there are less than two weeks until Christmas and Hanukkah, so I’d say it’s the perfect time to get out in the city and explore. Schools are almost out for the year and Chicago is lit up with holiday cheer. What are you waiting for? Here are a few ideas to get you started for your most epic weekend yet!
Skate With Santa
Spend a special morning gliding through the skating ribbon at picturesque Maggie Daley Park, with Santa joining in on the fun! There will family holiday crafts, activities, and photos with Santa, of course.
Details: December 14, 10 a.m.–noon.; free to attend, skate rentals are $15
Breakfast With Santa at the Zoo
Enjoy breakfast with views of the nature boardwalk at Café Brauer, with a buffet of scrambled eggs, waffles, double-smoked bacon, and more. Afterward, visit the cookie-decorating station before hanging with Santa for that iconic photo.
Details: December 15, $45 for 13 and older, $20 for ages 1–12, free for tots
Ski With Santa at Wilmot Mountain
You can sit on Santa’s lap, sure, but why not hit the slopes and ski with him! Wilmot Mountain is a close drive from Chicago, and it’s a great chance to get out and ski. Santa will be on the slopes that weekend, too, and around for dinner afterward with Mrs. Claus and the elves for pictures in the photo booth and free cookies after dinner.
Details: December 19 and 20, 3–8 p.m.
Gingerbread Decorating at Aster Hall
Take a break from holiday shopping for a bite to eat at downtown’s Aster Hall. The glam food hall is hosting a gingerbread-decorating event, where you’ll get four gingerbread cookies and a premade gingerbread house. The event scores you a $30 gift certificate to the hall that you can use for lunch or to come back another day.
Details: December 21, 10:30 a.m.–1 p.m.; $50, which includes a $30 Aster Hall gift card
Santa Suite at the Swissotel
Who says Santa can’t ski? Well, we aren’t sure about his skills, but we do know that he’s throwing a great aprés-ski-themed party at the Swissotel. The 2,000-square-foot presidential suite becomes Santa HQ, where elves show you around, offering activities and treats like letter writing to the North Pole, face painting, hot cocoa, and more!
Details: Weekends in December through Christmas; $15
Herschel and the Hanukkah Goblins
Hanukkah is in a few weeks, and this production, full of music and fun, tells the story of the holiday in a creative way. The play has been going for 32 years, so they must be doing something right!
Details: December 7–29, weekends; $25 for adults, $20 for kids
Make a Date With Santa
If you are ready for the holidays, you’re in luck. The Fashion Outlets of Chicago has brought Santa HQ back—and better than ever. There will be plenty of treats and fun attractions to get you in the festive mood!
Details: Through December 24
It’s the most wonderful time of the year at the Lincoln Park Zoo! Lights brighten up every corner of the zoo, with some that are worth the few extra minutes to pause and watch dance. Food and drink are aplenty, and everyone there is filled with joy. It’s a Chicago holiday must!
Details: Through January 5; free
The beloved bear returns for the holiday season to the Broadway Playhouse to warm the hearts of families, who will see the production taken straight from the pages of the childhood-favorite book. The one-hour run time makes it perfect for toddlers and up.
Details: Through January 5; $16
Home Alone at the Whitehall Hotel
Looking for a staycation (or vacation) adventure? The Whitehall is channeling its inner Kevin for a Home Alone extravaganza. Watch the movie in a roomful of little details reminiscent of the film, and then indulge like any kid who is home alone would—with pizza, treats, and a hot fudge sundae.
Details: Through January 5, room rates vary per date
“Christmas Around the World”
Whether you celebrate Christmas or not, this annual show at the Museum of Science and Industry is worth your time. It’s hard not to be wowed by the 50 trees that showcase how the holidays are celebrated around the world. While you’re there, explore the other exhibitions that make this museum one of the best in Chicago!
Details: Through January 5
Chicago Trolley Holiday Lights Tour
A trolley ride to see the city all lit up in its glory isn’t half bad! When you pair that ride with hot cocoa, caramel crisp popcorn, and 3-D glasses for the ZooLights stop, it becomes pretty amazing. This is a great way to tour the city and holiday fun for the whole family.
Details: Check website for dates and times; $35 for adults and $20 for kids
See The Nutcracker
There are few things more classic for the holidays than seeing The Nutcracker, and the Joffrey Ballet always puts on a stunning performance. This two-hour show (make sure your kids have the attention span!) will mesmerize from start to finish.
Details: Through December 29
Visit the Christkindlmarket
It’s that time of year to spread joyous cheer, bundle up, and eat festive snacks at this annual market. Find giant pretzels for the kids and a boot of warm beverages for you, and explore all the fun, German-inspired goods across the market.
Details: Through December 24; free to attend
Polar Express Train Ride
Hop aboard the Polar Express for a one-hour adventure complete with a reading of The Polar Express, hot chocolate, and cookies on the way to meet Santa. A souvenir golden ticket and sleigh bell are yours to keep, and there will be plenty of other fun surprises along the way!
Details: Through December 29; $60 for adults, $50 for kids
Teddy Bear Tea at the Hotel Zachary
Grab your favorite teddy bear and head to this Wrigleyville hotel for a special teddy bear tea, running weekends through December 29. Sip teas from Rare Tea Cellar, drink house-made hot chocolate, savor tea sandwiches and sweets, and listen to a tale from a guest storyteller.
Details: Saturday and Sunday though December 29, at 11 a.m. and 1:30 p.m.; adult tea service is $55 and children ages 2–12 is $35
Winterland at Gallagher Way
In the summer, Wrigleyville is all about the Cubs, and in the winter it turns into a holiday extravaganza! There’s always something to do at Gallagher Way this time of year, from its Christkindlmarket and ice-skating to wreath making and much more. It’s worth checking out this family-friendly outdoor space.
Fifth Third Bank Winter Wonderland at Navy Pier
Prepare to be amazed by 170,000 square feet of holiday fun as Navy Pier’s festival hall is completely transformed into a winter wonderland. Take photos on the blue carpet, climb through the extreme obstacle course, hit the rides, decorate cookies, ice-skate, and so much more.
Details: Through January 12; $10–$28