Santa sightings in Chicago
Between shopping stints at the 900 Shops, visit with Santa to spread some holiday spirit. On the mall's third floor you’ll find Santa at his elegant throne made of red fabrics, gold hues and silk pillows. Christmas comes early for visitors, too, as each child gets a gift. You can see Santa through Dec 24.
Celebrate the holidays with a merry breakfast with Santa at Winnetka Community House on Dec 5 from 8:30–11:30am. Especially popular with young families, the event includes a full buffet, a chance to meet Santa and get a free photo, personalized holiday crafts, and even a free book from Mrs. Claus’s library. Guests are invited to bring an unwrapped toy for Toys For Tots. Get tickets ($25) early by purchasing here or at the Winnetka Community House’s front desk.
Learn a little history before hopping on Santa's lap. The History Museum is home to the only train car remaining from the original fleet sent out to run on the El tracks. Santa makes appearances from noon to 3pm on Saturdays and Sundays from Dec 5 to 20.
Santa takes his sled to this kiddie favorite play café for two events this winter. Enjoy Santa, playtime and holiday snacks on Dec 18 from 4–6pm ($20 for the first kid, $18 for sibling, includes Santa photo) and come back with the family for a catered dinner on Dec 20 from 5–7:30pm with Santa along with live music and plenty of holiday cheer ($20 per person includes photo).
Ever since its iconic heyday as Marshall Field’s, the State Street Macy’s has been Chicago’s preeminent destination for Christmas merriment. The department store goes all out for the season, unveiling its famous animatronic window scenes and adding wreaths, mistletoe and ornaments throughout the store. But the real tradition is visiting with Santa in the fifth floor children’s department, a whimsical Santaland outfitted with Santa’s house, elves, snow, sleigh and all the magical accoutrements.
Santa is an avid reader and will share some of his favorite stories at this Oak Park spot from 9–10am on Dec 15. Parents can sip on coffee and nibble on fresh pastries while the little ones sip on juice boxes during story time. And it's all for a good cause—bring in a canned food item to support the Oak Park River Forest Food Pantry.
Finish your holiday shopping with the tiny threads at this boutique while your kids smile for complimentary digital photos with Santa on Dec 19 from 3-5pm. Everyone will go home with a candy cane or two, and mom and dad can sip Bow Truss pour overs in the Guide Shop making it a win-win for all.
The ultimate wintry wonderland is at Oakbrook Center, where Dreamworks Animation teamed up with Santa Claus for interactive holiday fun. The “Adventure to Santa” experience features a 2,000-square-foot Christmas cottage and an entrancing journey to the North Pole led by Shrek, Donkey and other Dreamworks characters. The tour takes kids on an animated trek that allows attendees to digitally create and decorate a sleigh before voyaging to the North Pole. Once inside the cottage, Santa’s sitting room resembles a fairy tale library, with bookcases, a tree, baskets of letters, cookie platters and other cozy cottage comforts. Families can reserve slots ahead of time at www.oakbrookcenter.com.
Don't miss the Santa Brunch on Dec 13. Spend the morning playing with the kids at Maggie Daley Park and then head across the street to Remington’s to indulge in a festive meal filled with goodies like gooey Monkey Bread. The Jolly Old Elf will be roaming the restaurant all day (11am–2pm) so kids of all ages can snap photos with the bearded man and put in their wish list requests. If you miss Santa on the 13th, he’ll be at sister restaurant The Windsor the following Sunday, Dec 20, spreading even more holiday cheer.
Even Santa enjoys a little sunshine sometimes, so he’ll stop by the bright and sunny summer-inspired restaurant on Dec 20 between 11am–2pm and 5–7pm to hear the kiddos' wishes and hand out holiday treats (cookies, perhaps?). If you miss him the first time around, he’ll be back for last-minute requests on Dec 23 from 11am–3pm. Reservations required.
If there’s anyone who can steal the spotlight from the Chicago Bears, it’s Mr. Claus. Santa settles into Soldier Field on Dec 5 at 10 am for his ninth annual Breakfast With Santa, where families are welcome to dine at the United Club and sit with Santa alongside a nostalgia-inspired train display that looks like it’s been plucked from a Christmas special. The breakfast will also include cookie-decorating, a toy drive and a handmade ornament contest.
Even Santa deserves some glitz and glamour, and this year he’s finding his holiday retreat with penthouse views on the 41st floor of Swissôtel Chicago. Of course, the generous and jolly old man is inviting you to relax too, as the Santa Suite will be open to hotel guests and the public starting Dec 3. Check out the full schedule here.
You can take guided tours (led by the Swissôtel elves) of the five-room suite, which will be decked out in holiday garb. Don't miss the letter-writing station for those important wish lists, and enjoy complimentary treats and a little gift for each child who has been nice this year.
If French toast sticks and cheesy eggs sound like ideal festive fare, head to Tavern on Rush for brunch with Santa on Dec 13 from 10:30am–2:30pm. The big man will take a day off from all that gift-wrapping for a leisurely brunch at this Gold Coast spot decked out in holiday decor. He’ll settle in on a throne in the upstairs dining room overlooking Rush Street and Bellevue Place, where kids can sit on his lap and put in their Christmas requests.