Where is Santa? Our 2023 Guide to Find the Jolly 'Ol Fellow in Chicago

By Debra Flanagan, Macaroni KID Chicago Northside November 14, 2023

This Guide is sponsored by Michele Taylor Photography
Michele Taylor Photography is a portrait studio that specializes in newborn, children, family, high school senior and pet photography. We are located in the Lakeview/NorthCenter neighborhood.
We also offer special petite sessions during the year including holiday and Santa, who is visiting our studio Saturday, November 18th! 
Follow us on Instagram to see our latest work and find out about our special sessions @michele_taylor_photography

1641 W Irving Park Rd/708-359-8881/

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.

Chicago Northside:


Brunch with Santa at Replay Andersonville
Santa Claus is coming to town! Enjoy delicious brunch, holiday music, and a visit from Santa.
Dec. 16 and Dec. 24, 11am

Holiday Cookie Decorating with Santa Claus at The Guesthouse Hotel
The event will feature an array of scrumptious sugar cookies, gingerbread men, and an assortment of decorative toppings. Children and adults alike can let their creative culinary talents shine as they design their own edible masterpieces. Our spacious event space will be transformed into a winter wonderland, complete with holiday music and decorations to make you feel like you're in Santa's workshop.
To make this event even more magical, don't miss your chance for a photo op with Santa Claus, who will be available after the cookie decorating fun. Capture the joy and wonder of the holiday season with your loved ones and Santa in the background.
Dec. 10, 10am-2pm

Photos with Santa at The Guesthouse Hotel
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. Dogs are more than welcome to join in on the holiday fun. Don't miss this opportunity to create treasured moments with your loved ones, both two-legged and four-legged, in Andersonville this holiday season. Pre-register for your time block for holiday photos with Santa.
Dec. 3, 10am-2pm

The Sofo Tap
Doggy Days: Photos with Santa and your pooch
Dec. 9, 12pm-3pm

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 Santa. It is entertainment for the whole family and includes kaffestuga, Lucia processions and folk dancers.
Dec. 2 and Dec. 3

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. 9 and Dec. 10, 9:00am-11:00am

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. 17, 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 from Elsa, Olaf and Santa! And don't worry if it's chilly -- attendees will be kept warm with complimentary hot chocolate, coffee and donuts.
Nov. 19, 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. 25-Dec. 23

Roscoe Village Winterfest
On Sunday, come out and enjoy all sort of fun activities. Santa will be at Cubbington’s Cabinet (2015 W. Roscoe St.) from 1-5pm. We’ll have horse-drawn sleigh rides outside of John’s Place (2132 W. Roscoe) and an Ice Sculpture Demonstration (outside of Ki House – 2058 W. Roscoe) from 1-3pm . It’s going to be a packed weekend of holiday fun you won’t want to miss!
Dec. 3, 1pm-5pm

Santa's Workshop Christmas Pop-up at Old Crow Smokehouse
The Wrigleyville barbecue spot morphs into Santa’s Workshop for the season. Giant Christmas balls, white lights, Christmas trees, and a giant Christmas rocking horse set the holiday scene, while the menu features comfort food favorites like Old Crow Pot Pie, Short Rib Sandwich, Christmas Ham Sandwich and Sugar Cookies. Take a free picture with Santa on the roof with his sleigh and reindeer. Children welcome until 9pm.
Beginning Nov. 20

Southport Holiday Stroll
The Southport Holiday 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 Stroll is free to attend and includes special deals from local businesses, carol singers, photos with Santa, holiday treats, and other surprises!
Dec. 1, 5pm-9pm

Wintrust Winterland at Gallagher Way
Santa has landed in Gallagher Way! You, your kids, and pets have a chance to visit Santa every Friday, Saturday, and Sunday from November 24 through December 23! Guests can take photos with Santa in his workshop, located in Wrigley Field’s C.D. Peacock Premier Entrance lobby. The lobby is accessible from the Gallagher Way Gate, located in Gallagher Way. There is no entrance fee and photos are available for purchase. Pets are only allowed on Sundays.
Nov. 24-Dec. 23

  • Fridays: 3 p.m. - 8 p.m.
  • Saturday - Sunday: 11 a.m. - 5 p.m.

Lincoln Square/Ravenswood

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 4:30 - you can even snap a photo with him with your phone.
Nov. 25, 4:30pm

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. 25, 10am-3pm

North Center

2023 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 will arrive on his grand sleigh for photos throughout the day. The Winter Queen will also be there walking through the Town Square saying hello to all the kids!
Dec. 9, 12pm-6pm

Itsy Bitsy Play and Cafe
Join for a special visit from Santa, and story time with Connections Academics - Registration is required ($35 per child) and includes:

  • A visit with Santa (Professional photographer prints available for purchase from TK Photography)
  • Story time with Connections Academics
  • Open Play 
  • Hot Chocolate (1/child)
  • Coffee (1/adult) 

Dec. 3, 2pm-4pm

Michele Taylor Photography
Michele Taylor Photography is a portrait studio that specializes in newborn, children, family, high school senior and pet photography. We are located in the Lakeview/NorthCenter neighborhood. Currently offering a special petite session with Santa.
Nov. 18

Greater Chicago:

Edison Park

Santa Express
Santa will arrive on the 10:04am train. Follow Santa to the tree lighting ceremony. Head over to Moretti's for visits and pictures with Santa, Grinch, a balloon artist, face painting, cookies and milk, pizza party, and holiday trolley rides across the street at the Metra station. First 300 children will receive a holiday goodie bag.
Dec. 2 from 10:04am-1:30pm

Hyde Park

Hyde Park Holly-Day 2023
Enjoy Hyde Park Holly-Day with FREE family fun - Soul Santa, ice carving, crafts, costumed characters, dance, reindeer with sleigh & more.
Dec. 2, 10am-4pm

Museum of Science and Industry
Visit with Santa in his festive photo Holiday Studio. The whole family can pose for a photo with the jolly man himself and bring home a souvenir photo. Requires additional tickets (available online) and are not included in Museum Entry. Capacity is limited and subject to availability.
Weekends and additional peak days from Nov. 18 - Dec. 24

Lincoln Park

Jingle Jam at New City-ville
Celebrate the holiday season at this indoor event at New City featuring visits with Santa and Mrs. Claus, festive holiday music, and more!
Dec. 2, 4pm-7pm

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. 17 and Dec. 22, 11am

The Loop

The Berghoff Restaurant
Share some schnitzel with Santa this holiday season at the Loop's historic Berghoff Restaurant.
Select dates Nov. 24-Dec. 23, 1pm-7pm

Breakfast with Santa at The Fairmont Chicago, Millenium Park
In collaboration with Make-A-Wish® Illinois, community members, and hotel guests will have the opportunity to enjoy a delightful breakfast with the one and only Santa Claus. The event promises many engaging activities, including memorable photos with Santa, creative cookie decorating, and a festive antler decorating station, not to mention a delectable breakfast buffet featuring an array of treats, including mimosas and Bloody Marys.
Dec. 3, 9:30am-12:00pm

CTA Holiday Train
The magic is back! 2023 is the 32nd 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. 24-Dec. 18

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 Worskshop, Macy’s Santaland will open for in-store visits at Macy’s State Street.
Nov. 4-Dec. 24

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. 25, 10am-6pm

United Club at Soldier Field
Welcome in the holidays at Soldier Field at the annual Breakfast with Santa event inside the United Club. Featuring a lavish buffet breakfast inside the United Club, a visit and photo with Santa and his Elves, Pocket Circus, Train Display from Yesteryear, Holiday Arts & Crafts, and much more!
Dec. 2, 9:30am-11:30am


Photos and Visits with Santa
Visit Santa at HIP's Center Court and each child (12 and under) will receive a free holiday backpack.
Nov. 18 - Dec. 24

River North

Brunch with Santa
Maggiano's invites you and your family to join us as we celebrate the magic of the season. Santa and Mrs. Claus are taking a break from their busy schedule to come to Maggiano's Downtown Chicago for brunch. Enjoy a delicious Maggiano's Style Brunch Buffet featuring all of yours and Santa's favorites. Wear your favorite holiday clothes or an "ugly" sweater and dance and sing along with our Holiday DJ while they play your favorite holiday tunes while we decorate cookies and have crafts to participate in as a family. 

Pre-purchase tickets before so you can have the opportunity to meet and greet with Santa and Mrs. Claus and join the holiday cheer!
Nov. 26 and Nov. 26, 10:30am-1:00pm

Light Up the Lake, Navy Pier
Santa is coming to Navy Pier starting November 24th through December 23rd. Check the schedule for his visits to Reunion’s Santa’s Southern Workshop and Harry Carry’s Lakefront Lodge.
Nov. 24-Dec. 23

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. $50 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.

Offshore Rooftop
It's that time of the year again - Santa is stopping by Offshore to check in on all the good little boys and girls - and to get their Christmas wish lists! Come meet with Santa, take pictures and have some brunch at the World's Largest Rooftop at the iconic Navy Pier.
Dec. 10, 10am-2pm

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. 17, 10am-2pm

Santa Sails the Seadog to Harry Carry's
Santa will trade in his sled for the Seadog by City Cruises and sail to Navy Pier for Brunch with Santa at Harry Caray’s Tavern’s new pop-up, the Lakefront Lodge. Kick off the holiday season by welcoming Santa as he makes his grand entrance by boat on the iconic Seadog before heading to Harry Caray’s Tavern for photo ops, delicious brunch bites, and live holiday music by a local Chicago musician.
Nov. 19, 12pm-3pm

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.
 $18 for one adult; $8 for each child 17 years and under. Ticket includes same-day museum admission.
Dec. 2, 8:45am-2:00pm

The Sweetest Santa on the Mile at Water Tower Place
The Sweetest Santa on The Mile is a whimsical, family-friendly, and candy-packed Holiday experience that will fill your senses with sweet delight. Immerse yourself in the sugary wonderland and capture the magic with the festive photo opportunities scattered throughout. But that’s not all! Make your memories even sweeter with a special visit to the Sweetest Santa on the Mile. While the candy-filled photo pop-up is free for all to enjoy, Santa photos are available for an additional fee.
Nov. 17-Dec. 24

Northern Suburbs:


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. 30-Dec. 24


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.
Select dates Nov. 17-Dec. 24
Pet Nights With Santa: Nov. 20, 27, and Dec. 4, 4pm-7pm
Sensory Santa Event: Dec. 3, 9am-10am


Santa's Time Warp Adventure
Volo Museum Presents "Time Warp Express" A Holiday Adventure to Save Santa". 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, Nov. 3-Dec. 23, 5pm and 7:30pm

Happy Hunting!

For more Holiday Activities click here!