This Guide has been generously sponsored by Music Theater Works
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For more than a century, audiences around the world have been inspired by the story of ANNIE, the spunky, red-headed orphan whose unshakable optimism transforms everyone she meets, including billionaire Oliver “Daddy” Warbucks. Winner of seven Tony Awards, including Best Musical, ANNIE shines with some of the most beloved songs in musical theatre history, such as “Tomorrow,” “NYC,” and “You’re Never Fully Dressed Without a Smile.”
Tickets are now on sale for Music Theater Works’ ANNIE with guests 25 years old and younger available at half-price - perfect for the whole family. Playing for a limited time, December 19 - January 4 at the North Shore Center for the Performing Arts in Skokie. Tickets and more information at MusicTheaterWorks.com
Looking for a place to meet Santa for a special photo op, or a chance to tell him what's on your Christmas list, in person? We've gathered up a nice list of places where you can find Santa this season.
Northern Suburbs:
Lincolnwood
Lincolnwood Town Center
Bring the family to capture holiday moments with Santa that you’ll treasure forever! You can save time this holiday season by reserving your photo time slot in advance -- Reservations are encouraged! (However, walk-ins are also welcome!) For questions and information regarding Santa Photos, please contact Cherry Hill Programs at 800-475-4401
Nov. 28 - Dec. 24
Rosemont
Fashion Outlets of Chicago
The magic of the holiday season comes alive with a visit to Santa’s winter wonderland. A visit with Santa is always free and photo packages are available for purchase.
- Pre-book now and receive a free personalized digital message from Santa before your visit, powered by Portable North Pole.
- Show up at your designated time.
- Share your wish list with Santa and his helpers.
- Make a lasting memory and get your photo taken with Santa.
Select dates Now - Dec. 24
Pet Nights With Santa: Nov. 24, Dec. 1 & Dec 8, 4pm-7pm
Sensory Santa Event: Dec. 7, 9am-10am
Volo
Santa's Time Warp Express
Volo Museum Presents "Time Warp Express." Prepare to be swept away into a world of enchantment and timeless holiday magic with this extraordinary Christmas event, hosted at the Volo Museum in Volo, Illinois, offers a unique journey where the past, present, and future of Christmas come together in a heartwarming celebration.
1. Grams Central Station: Begin your adventure in the charming Grams Central Station where, you can enjoy delicious cookies and comforting hot chocolate, both provided as complimentary treats for all guests.
2. Meet Santa and His Elves: No Christmas adventure would be complete without a visit from Santa Claus himself! Don't forget to capture this magical moment with a complimentary photo session, ensuring cherished memories that will last a lifetime.
3. Time Warp Express: All aboard the enchanting Time Warp Express, a trackless train or trolley that will transport you and your fellow passengers on a captivating journey through time. As you glide through beautifully decorated surroundings, immerse yourself in a captivating Christmas tale brought to life through interactive storytelling. You'll feel like an integral part of a classic holiday fable, surrounded by enchanting scenery and captivating characters.
Fridays and Saturdays, Now - Dec. 31
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Greater Chicago:
Edison Park
Santa Express
Santa makes his grand entrance on the Metra at 10:48 AM sharp—don’t be late! The first 400 children will receive a festive goody bag packed with treats, courtesy of Tony’s Italian Deli. You’ll also pick up your Kringle Krawl game card right at the station, so arrive early!
Once Santa arrives, the holiday fun begins! Stroll through participating Edison Park businesses offering seasonal activities, sweet treats, and family-friendly surprises. Collect a stamp at each stop and complete your game card for a chance to win a $100 Amazon Gift Card—we’re drawing five lucky winners!
Dec. 6, 11am-2pm
Hyde Park
Hyde Park Holly-Day 2025
Enjoy Hyde Park Holly-Day with FREE family fun - Soul Santa, ice carving, crafts, costumed characters, dance, reindeer with sleigh & more.
Dec. 6, 10am-2pm
Lincoln Park
Summer House
Santa is stopping by to hear what’s on your kid’s wish list. Stay for lunch and enjoy fresh salads, homemade pizzas, wood-grilled entrees, and more. Don’t miss this family-friendly event! Reservations are limited.
Dec. 14 and Dec. 19, 11am
The Loop
The Berghoff Restaurant
Share some schnitzel with Santa this holiday season at the Loop's historic Berghoff Restaurant.
Nov. 24, Dec. 2, 9, 16, 22 & 23, 1pm-7pm
CTA Holiday Train
The magic is back! 2025 is the 34th year for a beloved Chicago tradition: The Allstate CTA Holiday Train. The CTA Holiday Train is a magical way to spot Santa and exchange a few words if you are lucky. This year, Santa and the CTA are excited to welcome back riders aboard both the Allstate CTA Holiday Train and the popular Allstate CTA Holiday Bus. The Allstate CTA Holiday Train will travel all 'L' lines beginning in late November through late December as part of regular rail service, making stops at all stations along the respective routes. Schedules for each rail line will vary. Normal CTA fares apply.
Nov. 28 - Dec. 22
Santaland at Macy's
Book your time to join the line—it’s the only way to meet & take a photo with Santa in person. An enchanted world showcasing Santa’s Village and Workshop, Macy’s Santaland will open for in-store visits at Macy’s State Street.
Now - Dec. 24
Selfies with Santa at Skydeck Chicago
Experience Instagram-worthy moments with the jolly man himself. Santa will be available for pictures from December 1-19 from 10am - 1pm. Find him strolling their lower-level immersive experience all the way up to #TheLedge.
Dec. 1 - Dec. 19, 10am-1pm
Sleighride Cruises
Set sail on the iconic Chicago River this holiday season with our Santa Claus Sleigh Ride Cruises! Join us for an unforgettable experience filled with festive cheer and fun for the whole family.
Friday, Saturday, Sunday, Nov. 21 - Dec. 21
Swissôtel Chicago Santa Suite
The Swissôtel Chicago transforms its 2,000-square-foot Presidential Suite into Santa’s Chicago holiday home. Visit on Santa Days for elf-guided tours of the Suite and meet Santa, where he will be seated at bedazzled holiday chair and capture memorable photos with little ones looking to make their wishes come true this holiday season. Visitors will also enjoy a letter-writing station for holiday wish lists, face painting and kids’ crafts, as well as a complimentary hot chocolate bar and gourmet holiday treat offerings. (You can also book your own private visit and stay.)
Nov. 28 & Dec. 12
Norridge
Photos and Visits with Santa
Visit Santa at HIP's Center Court.
Nov. 14 - Dec. 24
River North
Breakfast with Santa at Harry Caray's Tavern
Join us this December for our magical Breakfast with Santa, where holiday cheer comes to life for the whole family. We’ll be serving up festive holiday-inspired breakfast favorites, while the kiddos get to meet, interact with, and snap photos with Santa Claus himself in the beautiful Lakefront Lodge holiday pop-up at Harry Caray's Tavern.
Dec. 7 and Dec. 14, 10:30am-12:30pm
Navy Pier's Winter Wonderfest
Relive cherished memories and make magical new ones at Chicago’s favorite holiday experience. Step inside and kick off the season with rides, slides, and festive fun. From thrilling attractions like the Cliffhanger and Zero Gravity to family favorites like the kiddie train, bumper cars, and skating on The Verizon | Google Pixel Ice Rink-there’s something for everyone!
Dec 5. - Jan. 4
900 North Michigan Shops
For photos with Santa, a vintage sleigh has been nestled amongst a cluster of cheery pines, aglitter with hundreds of tiny holiday lights. While whimsical, woodland creatures frolic about in a blanket of fresh-fallen snow. Santa will be located on Level 3 of 900 North Michigan Shops. $55 Reservations include:
- A keepsake digital photo captured photographers, The Event Image Co.
- A dreamy, designer-inspired Winter wonderland setting
- A most fantastical Santa
- Digital download of photos, conveniently delivered on site
- A special toy from Santa (while supplies last.)
- Santa visits are reservation only. No walk-ins.
Nov. 19 - Dec. 24
Santa Brunch and Playtime at the Chicago Sports Museum
Bring your family and friends to enjoy a delicious brunch while the little ones have a blast playing in our interactive exhibits. Santa himself will be making a special appearance, so don't forget to bring your wish lists! It's the perfect opportunity to create magical memories and celebrate the holiday season. Don't miss out on this merry event!
Dec. 7, 11am-1pm
Santa Saturday at The Driehaus Museum
Driecember is here with Santa’s annual visit to the Driehaus Museum! Join him in our Front Parlor, share your Christmas wish list, and take selfies with jolly old St. Nick. This magical, family-friendly event will fill up fast so make sure to book early. Time slots are 15 minutes each.
$25 for adults; $15 for each child 17 years and under. Ticket includes same-day museum admission.
Dec. 6 & 13, 9am-12pm
Where is Santa at Water Tower Place
Don't miss Santa pictures at Water Tower Place! Walk ups welcome every day until closing time. Special events include pet parties, pajama parties, sensory-friendly visits, and more.
Now through Dec. 24
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Chicago Northside:
Andersonville
Cookie Decorating with Santa at The Guesthouse Hotel
Join us for a delightful holiday cookie decorating event with Santa Claus. This intimate experience at The Guesthouse Hotel invites the whole family to interact with Santa while decorating scrumptious cookies.
Dec. 14, 9:30am-2:30pm
Photos with Santa Claus at The Guesthouse Hotel
Get professional family photos with Santa Claus at The Guesthouse Hotel and build some beautiful holiday memories. Get ready to make your holiday season even more special with our Photos with Santa event at The Guesthouse Hotel in Andersonville! This festive occasion allows families to reserve a spot ahead of time and capture wonderful memories with Santa Claus by a professional photographer.
Nov. 23, 11am-4pm
Swedish American Museum
Julmarknad is the Museum’s annual Christmas Bazaar, where traditional Scandinavian and modern handicrafts will be available for purchase. Visit the Children’s Museum for crafts, games and a special visit from Tomten (Santa.) It is entertainment for the whole family and includes kaffestuga, Lucia processions and folk dancers.
Dec. 5 - Dec. 7
Breakfast with Tomten (Sweden's version of Santa) is one of the Swedish American Museum’s most popular family event of the year! Join them on either Saturday or Sunday for a Swedish pancake breakfast with traditional crafts, a special visit from Tomten, and more.
Dec. 13 and Dec. 14, 9:00am
Julmiddag - A festive and traditional Swedish Christmas Smörgåsbord will be catered by Tre Kronor. Tomten (Santa) will be on hand to give julklappar (presents) to all the children. There will be a Lucia procession and everyone is welcome to dance around the Christmas tree.
Dec. 21, 5pm
Lakeview/Roscoe Village
Community Tree Lighting
Join us for the annual Lakeview Tree Lighting Ceremony! The event will take place at the intersection of Lincoln, Southport & Wellington outside of St. Alphonsus, and will include holiday tunes and carolers, festive gift bags and surprise appearances including Santa! And don't worry if it's chilly -- attendees will be kept warm with complimentary hot chocolate, coffee, pressed juice, pizza, and donuts.
Nov. 23, 6pm
Hotel Zachary
Enjoy a special holiday-inspired breakfast buffet, featuring an assortment of options for both children and adults to enjoy, while Jolly Old Saint Nick relaxes near the fireplace, waiting to visit with good boys and girls and listen to their holiday wishes.
Saturdays and Sundays Nov. 29 - Dec. 21
Roscoe Village Winterfest
Join us December 7th to kick off the holiday season by gathering with friends and family at our annual Winterfest. Have a festive weekend starting with a tree lighting, shopping at our one-of-a-kind boutiques, hot chocolate galore, and holiday cider. Then, bring the family for a horse-drawn sleigh, children’s activities, caroling, and, of course, Santa!
Dec. 7
Southport Holiday Cocktail Stroll
The Southport Holiday Cocktail Stroll is a longstanding tradition in West Lakeview where break out the holly and stay open late offering special holiday deals and festivities. The Southport Holiday Cocktail Stroll includes special deals from local businesses, carol singers, photos with Santa, holiday treats, and other surprises!
Dec. 5, 5pm-9pm
Winterland at Gallagher Way Tree Lighting
We're kicking off the holiday season and the official opening of Winterland at Gallagher Way with the Tree Lighting Ceremony on Friday, December 5. Join us with your friends, family and neighbors for an evening of holiday cheer with special performances, giveaways and more festive fun. The Winterland Tree Lighting Ceremony is free and open to the public.
Cradles to Crayons will be on site accepting donations for the holiday season.
Afterwards, stick around Winterland to enjoy the festivities. Stroll around Christkindlmarket, ride the Holiday Train, visit with Santa and more.
Dec. 5, 6pm
Winterland at Gallagher Way
This holiday season, stop by Winterland at Gallagher Way with friends and family. With music, Santa, seasonal food and drinks, and rides, you can expect plenty of free holiday cheer anytime you visit Gallagher Way! Santa's Workshop is open Fridays 4pm-9pm and Saturdays and Sundays 11am-5pm.
Nov. 28 - Dec. 21
Lincoln Square/Ravenswood
Ravenswood Pictures with Santa
Santa will be visiting Ravenswood during Small Business Saturday, giving your children and/or your pets the opportunity to get their pictures taken with him! Santa starts the day on Damen Avenue at The Perfect Cup where kids can get a chance to sit and talk with him. (free) Then, Santa will travel over to Urban Pooch on Ravenswood Avenue where you'll be able to capture the magical moment of your pets sitting with him. (free)
Nov. 29, 10am-12pm, Pets 1pm-3pm
Lincoln Square Tree Lighting at Giddings Plaza
Invite your friends and family to celebrate what makes the Lincoln Square and Ravenswood community so special during the annual Tree Lighting ceremony in Giddings Plaza. It's the perfect way to wind down your Small Business Saturday shopping, or get together right before going to dinner at one of the many local restaurants in the area. And be sure to grab a German glühwein or hot cider from DANK Haus German Cultural Center while you're there. Santa will also be at the tree for a meet & greet starting at 4:45 - you can even snap a photo with him with your phone.
Nov. 29, 5pm
North Center
2025 Holly Jolly Holiday Market
Join for a holly jolly good time! There will be plenty of merchants, food and drink vendors, amazing entertainment and more! Santa and Mrs. Claus will arrive on his grand sleigh for photos on Saturday and will bring special guests with him on Sunday, to walk through the Town Square saying hello to all the kids!
Dec. 13 and Dec. 14, 11am
Happy Santa Hunting!
For more Holiday Activities click here!
