It’s the most wonderful time of the year, and that goes double in Chicago, where dozens of seasonal events help the whole family get into the holiday spirit

With only a few weeks to pack it all in, choosing what seasonal activities to add to your family’s already action-packed calendar can be a stressful undertaking. There is no lack of light displays, live performances, train rides, seasonal food and drink offerings, and winter activities to choose from, so you truly have your pick of near-endless—and endlessly unique!—ways to help celebrate the holiday season. Better yet, there are even a few festivals where you can find it all in one place. So get out there and have some good ol’ fashioned festive family fun. There’s no time to waste! (Not even on Thanksgiving!)

Holiday Festivals in and around Chicago

Turns out, you can, in fact, have it all! A handful of seasonal festivals serve as a one-stop shop for a laundry list of holiday bucket list entries. Most of these venues include millions of sparkling lights, ice skating, holiday gift markets, live performances, and much more! Go for an hour or make a day of it, but rest assured there’s something for everyone.

The Village of Rosemont

Visit Rosemont for festive activities for the whole family to enjoy. After all, the village's slogan is "It's All Here," and no time is this truer than during the winter holidays. From ice skating at the Chicago Wolves Ice Rink in Parkway Bank Park, to a visit with Santa while getting all your shopping done at the Fashion Outlets of Chicago, there's no escaping the holiday feels. And when you need a break from finding gifts for your fam, there are endless dining and entertainment options to choose from, too. Not to be missed is the Sparkle Light Festival lights display (Nov. 23-Jan. 1) at Impact Field. The popular festival will include five illuminated villages with millions of sparkling lights, custom 3D holiday features, an ice tube slide, a holiday train adventure, and plenty of festive food and drinks. Plus, there's a Rudolph's Kids Zone and Deck the Walls maze, both new this season.

Dates: Nov. 19-Jan. 29

9501 W. Devon Ave.
Rosemont, IL


Don’t miss the chance to explore this holiday season at the Amaze Light Festival in Chicago! This wonderland of light welcomes guests of all ages to an all-immersive storybook experience highlighting themed worlds of displays and activities. At the Amaze Light Festival, you can find yourself mesmerized by colossal 3D lighted decor, dynamic live performances, an icy tubing hill, and an Arctic Express train. Visit the holiday market and then stop in and grab a treat at Sparky’s Sweet Spot.

Dates: Select dates from Nov. 18-Jan. 8

Odyssey Fun World
19111 Oak Park Ave.
Tinley Park, IL

Jack Frost Winter Fest

The Jack Frost Winter Fest has something for everyone. Not only can you ice skate, drive a bumper car on the ice, axe throw, or have your fortune told, but you can even find your perfect Christmas tree in their urban tree farm. Between the 10,000 twinkling lights, the Chicago skyline backdrop, and super cute curated photo ops, you'll have plenty to share on your social posts. New this year? Winter tubing!

Dates: Opening in November

1265 West LeMoyne
Goose Island

Winterland at Gallagher Way

Winterland at Gallagher Way is sure to be better than ever this year. While the Christkindlmarket Wrigleville and Santa's Workshop will remain on the outside of Wrigley Field, they are being joined by a carousel. Head into Winterland within Wrigley Field to hop on the ice for skating or ice bumper cars. Surrounding the ice rink will be rides including a Wintertube, Hot Cocoa Cups, a Winter Whirl, and the Infield Express train. There will also be some season-themed carnival games, fire pits, and rentable private chalets.

Dates: Nov. 18-Jan. 8

3635 N Clark St.

Related: Timber Time! Christmas Tree Farms to Spruce Up Your Holiday

Holiday Tree and Menorah Lighting Ceremonies in and around Chicago

What better way to usher in the holiday season than by attending a tree or menorah lighting ceremony and witnessing first hand the joy on everyone’s faces as these holiday symbols are illuminated.


Illuminate 900 Holiday Tree Lighting

In the center of the 900 N. Michigan Shops, a 50-foot-tall tree will be lit by Santa himself. Accompanying Santa will be activities such as sugar-cookie decorating, live holiday performances, and take an “Elfie” with The Real Elf. Click here for tickets. Children 10 and under are free. A portion of proceeds will benefit Make-A-Wish® of Illinois.

Date: Nov. 17 at 6 p.m.

900 N. Michigan Ave.
River North

Chicago Christmas Tree Lighting Ceremony in Millenium Park

Kick off the holiday season at the 109th Annual Christmas Tree Lighting Ceremony. The Millenium Park Christmas tree is considered the "official" Chicago tree. There will be performances by a DJ and Cabaret ZaZou, Son Monarcas, Broadway In Chicago: Wicked’s Lissa deGuzman “Elphaba” and Jennafer Newberry “Glinda” singing “For Good”, Jumaane Taylor and Chicago Human Rhythm Project's Stone Soup Rhythms; and special guests Dreezy Claus and Sister Claus preceding the lighting at 6pm. The lighting will be followed by fireworks and a performance by Adia, an Electric Violinist and DJ.

Date: Nov. 18 at 5 p.m.

201 E. Randolph Street

"Light Up the Park" Tree Lighting Event

Rosemont’s Parkway Bank Park entertainment district kicks off the holiday season with its Light Up the Park event. A variety of family-friendly festivities will be available from 2-6 p.m., including visits with Santa and Mrs. Claus, free horse-drawn sleigh rides, carolers, and ice sculpting viewing. The 80,000 holiday lights will be lit, for the first time, at 5:30 p.m. The ice rink will be open from 11 a.m. to 10 p.m., and Parkway Bank Park’s restaurants and entertainment venues will also be open throughout the day.

Date: Nov. 19 at 5:30 p.m.

5501 Park Pl.
Rosemont, IL

Community Tree Lighting at St. Alphonsus

The event will take place at the intersection of Lincoln, Southport, and Wellington outside of St. Alphonsus Church, and it will include holiday tunes and carolers, festive gift bags, and surprise appearances from Elsa, Olaf, and Santa. Enjoy complimentary hot cocoa, coffee, and donuts.

Date: Nov. 20 at 6 p.m.

1429 W. Wellington Ave.

Arlington Heights Tree Lighting

Celebrate with a night of festive fun as the holiday lights are turned on at North School Park. There will be tons of family fun. Dickens era characters will be on trolleys, looping from Harmony Park to North School Park, 3:45 p.m.-6:45 p.m., sharing stories about Arlington Heights in the past. There will be ice carvers, photo stations, and even live reindeer.
Date: Nov. 25 at 4:30 p.m.

North School Park and Harmony Park
Arlington Heights, IL

Lakeview Menorah Lighting Ceremony

Gather around the community menorah for treats and festivities for the entire family!

Date: Dec. 18 at 6 p.m.

Lincoln & Marshfield

Holiday Parades in and around Chicago

Sure, you can watch them on television, but you can’t feel the beat of the drums in the marching bands, smell the popcorn from the Garrett’s parade float, or stand in awe of the giant character balloons from your couch. When you are on the street, you aren’t just watching the parade. In a way, you become a part of it.

BMO Harris Bank Magnificent Mile Lights Festival

Watch as the Co-Grand Marshalls of the parade, Mickey and Minnie Mouse, magically turn on the lights lining the road as this parade proceeds down Michigan Avenue. If you stay til the end, you'll get your first glimpse of Santa on his sleigh!

Date: Nov. 19 at 5:30 p.m.

Michigan Ave.
River North

Chicago Thanksgiving Day Parade

With all the excitement around Christmas and Hanukkah, let's not forget to celebrate Thanksgiving! After all, the Chicago Thanksgiving Day Parade has been a city tradition since 1930. The procession travels up State Street from Ida B. Well Drive to Randolph Street.

Date: Nov. 24 at 8 a.m.

State St.

Related: The Ultimate List of Free Things to Do in Chicago with Kids This Month

Holiday Trains in and around Chicago

It might not make sense, but trains and the holidays somehow go hand in hand. Go beyond the locomotive set around the tree, or the model exhibits, and board a real train themed for the holidays. It’s a unique way to see Santa, too!

Blackberry Farm Holiday Express

And what to your wondering eyes should appear? A decorated miniature open-air train that runs continuously through Aurora’s living-history museum. Catch the Holiday Express train around Lake Gregory amidst thousands of twinkling lights. It’s part of the farm’s annual Victorian Christmas celebration, Holiday Express, which includes music, storytelling in a historic schoolhouse, a visit from Santa, craft stations and a Reindeer Food Bar. Tickets go on sale Nov. 10.

Dates: Thursdays-Sundays throughout December

100 S. Barnes Rd.
Aurora, IL

CTA Holiday Train

Santa and his merry band of elves will make an appearance on every El line this holiday season. In fact, the big guy in red comes jingling his way through in grand style, pulled in a sled by faux reindeer. A gift from the Chicago Transit Authority, the festive El—decked out in colored lights, garland, bows and tinsel—arrives with pomp and glee, leaving you and your little ones smiling ear to ear long after your stop. You might even get a candy cane handout if you’re onboard.

Dates: Select days in December

Various locations

Happy Holiday Railway at The Illinois Railway Museum

Enjoy a 40-minute train ride for the whole family. See and visit with Santa Claus on the train. Treats and hot chocolate will be served and gifts will be given to children. Before or after your ride, visit the Model Railroad Exhibit or some of the museum's historic train exhibits.

Dates: Select days in November and December

7000 Olson Rd.
Union, IL

The Nutcracker Ballet Performances in and around Chicago

Watching this classic ballet on stage is often an unforgettable experience for kids—and this season’s Christmas showcases of The Nutcracker in Chicago are such impressive memory creators that it will be hard to choose just one.

The Art Deco Nutcracker at The Athenaeum Theatre

Set in 1920s America, Alexei Kremnev's The Art Deco Nutcracker is an upbeat yet traditional take on the much-loved holiday favorite and guaranteed entertainment for all. This year's production features award-winning rhythmic dancers, stunning set designs, and added scenes and characters. Familiar favorites The Sugar Plum Fairy, Mother Ginger, and the Nutcracker Prince will all be on stage to tell the tale.

Date: Dec. 3 at 2 p.m. and 7 p.m.

2936 N. Southport

The Dance-Along Nutcracker at the Chicago Cultural Center

The Dance-Along Nutcracker is any budding ballerina's dream come true, with the opportunity to participate in a short workshop with Ballet Chicago, and then watch them perform an abbreviated version of the classic ballet at eye level. The dancers are accompanied by the Lakeside Pride Symphonic Band under the gorgeous rotunda of the Chicago Cultural Center. The tiny dancers are frequently invited on stage to twirl, leap, and sachet alongside the professionals. This year's details have not yet been announced, but be on the lookout!

Date: Dec. 3

78 E. Washington St.

Duke It Out! Nutcracker at Nichols Concert Hall

The Music Institute of Chicago presents its holiday tradition, Duke It Out! Nutcracker, featuring the classical (Tchaikovsky) and jazz (Duke Ellington/Billy Strayhorn) versions of the holiday favorite in a music and dance performance. The performance is a family-friendly 60 minutes and is preceded by an interactive musical instrument "petting zoo." For those who can't attend in person, the show is also available via livestream.

Dates: Dec. 10 at 2 p.m.

1490 Chicago Ave.
Evanston, IL

The Joffrey Ballet's Nutcracker at the Lyric Opera House

The Joffrey Ballet's performance of The Nutcracker is a beloved holiday tradition for many families. Christopher Wheeldon's reimagined classic follows young Marie and the Nutcracker Prince on a Christmas Eve journey through the 1893 World's Fair, a dazzling spectacle of sights, sounds and enchantment. This annual holiday tradition celebrates both the magic of the season and the rich cultural heritage of Chicago.

Dates: Dec. 3-27

20 N. Wacker Dr.

The Nutcracker on Art on theMART

An animated digital display of The Joffrey Ballet’s The Nutcracker will be shown as part of Art on theMART, the largest digital art projection in the world. The presentation is set to the music of Tchaikovsky’s beloved score and runs nightly on theMART’s 2.5-acre river-façade.

Dates: Nov. 19-Dec. 30 at 8:30 p.m. and 9 p.m.

222 W. Merchandise Mart Plaza
River North

The Nutcracker at Hyde Park School of Dance

Hyde Park School of Dance brings together fans of ballet, modern, and hip hop with its annual presentation of Tchaikovsky's The Nutcracker at Mandel Hall on the University of Chicago campus. 

Dates: Dec. 9-11

1131 E. 57th St.
Hyde Park

More Holiday Performances in and around Chicago

Start loading up the calendar with shows—from plays to musical performances—that fill your heart with holiday spirit. 

Millennium Park's Holiday Sing-Along

One of our absolute favorite activities! Hundreds of holiday revelers gather around Cloud Gate for a stunning view of the city in its reflection, and to join local Chicago choirs in festive songs. Each week is a different performance group, and free song books are distributed.

Insider tip: Go early and get some skating in at the McCormick Tribune Ice Rink just below.

Dates: Fridays, Nov. 25-Dec. 16 at 6 p.m.

201 E. Randolph St.

Merry, Merry Chicago at the Symphony Center

Listen to the celebrated songs of the season performed by the best musicians in the city: the Chicago Symphony Orchestra. Arrangements both new and cherished will have you humming and singing along. Be ready for a visit from the man in red, too! 

Dates: Dec. 16-23

220 S. Michigan Ave.

Cirque Dreams Holidaze at The Auditorium Theatre

A world of delight and whimsy awaits families looking for a bit of over-the-top holiday fun. Cirque Dreams Holidaze is an annual tradition fusing a Broadway-style musical with contemporary circus artistry.  

Dates: Dec. 22-24

50 E. Ida B Wells Dr.

The Beatrix Potter Holiday Tea Party at The Station

Chicago Children’s Theatre invites families to celebrate the holidays at the company’s ever-popular, seasonal smash hit, The Beatrix Potter Holiday Tea Party. Kids are encouraged to dress in their holiday best, or just come as they’re comfortable, to this incredibly charming, meticulously designed puppet show starring Peter Rabbit and his favorite animal friends. After the show, go on stage to gently play with the puppets and take pictures. Then, head to the lobby for a festive spread of chocolate milk and cookies!  

Dates: Saturdays and Sundays, Nov. 19-Dec. 24

100 S. Racine
West Loop

Hershel And The Hanukkah Goblins at The Edge Theater

Strawdog Theatre Company, one of Chicago's oldest ensemble theater companies, presents a Hanukkah show for all ages. When a traveling troupe of actors comes to town only to find no one celebrating Hanukkah, they try to figure out a way to save the Hanukkah spirit STAT. In this adaptation of the Caldecott Honor-winning book, Strawdog brings the cherished story to life with music, puppets, and a heavy dose of theater magic. 

Dates: Dec. 10-31

1133 W. Catalpa Ave.

A Christmas Carol at The Goodman Theatre

The Goodman Theatre's production of the holiday classic serves up a heavy dose of cheer to enliven even the grouchiest of Scrooges. There is something about this timeless story, combined with the world-class actors of The Goodman, that keeps the "bah-humbugs" away. Extra special for 2022? This year marks the Goodman's 45th annual production of this timeless tale of kindness and compassion.

Dates: Nov. 19-Dec. 31

170 N. Dearborn

Elf the Musical at Drury Lane Theater

Based on the hit Christmas film, Elf the Musical is the story of a human, raised as an elf, that goes on a journey to find his birth father. His birth father is your basic Scrooge, until his new son teaches him and all of NYC about the true spirit of Christmas. The show is equally full of humor and heart-warming moments.

Dates: Nov. 9-Jan. 8

100 Drury Lane
Oakbrook Terrace, IL

Holiday Tea Experiences in and around Chicago

Take a break from all that shopping with an afternoon holiday tea experience to rest and recharge. Our fair city offers the time-old tradition that will turn a day of shopping with the kids into a cherished memory.

Palm Court Holiday Tea at The Drake

If you want to feel like royalty, afternoon tea at the Drake is for you. After all, Queen Elizabeth, Princess Diana, and the Empress of Japan—each of whom has enjoyed tea at the famous hotel—wouldn’t settle for just any cuppa. During the holiday season, Palm Court will transform into a winter wonderland complete with festive decorations, seasonal pastries, a harpist and even a merry band of carolers  Reservations can be made online at OpenTable or by calling 312-932-4619.

Dates: Nov. 3-Jan. 8

140 E. Walton Place
River North

Afternoon Holiday Tea at LondonHouse

Tea service in the Bridges Lobby Bar offers a stunning view of the Chicago River and its famous bridges. You’ll begin with a tea selection of Rare Tea Cellars and Sparrow Coffee teas and a basket of fresh scones and breads. From there, you’ll pick sweet and savory bites from a 3-tiered tower crafted by the culinary and pasty teams. 

Dates: Nov. 19-Jan. 15

85 E. Wacker Dr.

Holiday Afternoon Tea at The Peninsula

The Lobby is nothing short of spectacular during the holiday season. The menu features finger sandwiches including Smoked Salmon, Organic Egg Salad, Classic English Cucumber and Cranberry Chicken. Petite seasonal pastries with choux, chocolate and winter fruit creations as well as fruit and plain scones, house-made preserves and Devonshire clotted cream. Vegan, vegetarian and gluten-free options are available. Holiday carolers, Mrs. Claus and a string duo provide the entertainment (note: entertainment varies based on day of the week). For Holiday Tea, make your reservation via Tock.

Dates: Nov. 25-Jan. 8 at 2:30 p.m. and 4:30 p.m.

108 E. Superior St.
Near North Side

Teddy Bear Tea at Hotel Zachary

Create warm winter memories with high tea for you, your little one and their best stuffed friend with Teddy Bear Tea at Hotel Zachary. On Sunday afternoons, families are invited to enjoy a festive tea service, featuring Rare Tea Cellars. Children can indulge in a pot of house-made hot chocolate, tea sandwiches and light bites, scones, cupcakes, and more sweet treats. Reservations can be made on While you’re in the area, stop by Gallagher Way’s Winterland for non-stop holiday cheer. 

Dates: Sundays, Nov. 27-Dec. 18 at 1:30 p.m., 1:45 p.m., and 2:00 p.m.

3630 N. Clark St.

Holiday Tea at Vanille Patisserie

Vanille Patisserie’s French-inspired holiday tea experience will transport you and your bébés to the city of lights. Enjoy Vanille signature pastries, scones, and finger sandwiches while sipping on the finest of Benjamin’s Tea and Hot Chocolate with house-made marshmallows. 

Dates: Nov. 4-Jan. 8

2108 N. Clark St.
Lincoln Park

131 N. Clinton St.
Chicago French Market

Related: Small and Local Toy Stores to Support This Holiday Season

Holiday Markets in and around Chicago

Among all the merriment that the holiday season provides, it also requires—for many families—the hunt for the perfect gifts for loved ones. Thankfully, Chicago is one of the best cities in the nation for shopping, and this season in particular provides no shortage of places to help shoppers work their way through their holiday wish lists.


Bundle up for this outdoor market (which continues to run out of its flagship location in the Loop and an outpost in Wrigleyville) that brings the cherished tradition of the Christkindlmarket in Germany to Chicago and adds a heap of local charm. Each of the market’s signature wooden cabins topped with festive red-and-white-striped canopies are packed with handmade gifts, food and drinks from around the world and many are run by native German speakers. Shop, visit with Christkind, eat, enjoy free entertainment, repeat—and be sure to say “guten tag” to Santa Claus. 

Dates: Nov. 18-Dec. 24

Daley Plaza
50 W. Washington St.


Gallagher Way
3635 N. Clark St.

Holiday Pop-Up Market at Winter Walk on Wilson

Stroll the shops and businesses along Wilson Avenue and stop in at Wilson and Broadway to connect with Chicago Market and vendors offering snacks, holiday gift shopping, and more

Dates: Dec. 2 at 5-8 p.m.

Wilson Ave. and Broadway

Randolph Street Holiday Market at Plumbers Hall

With prices ranging from thrifty to extravagant, you’re sure to find something for even the pickiest of gift receivers this year. Peruse the market for smartly priced antique, vintage and modern goods – everything from embroidered hankies to estate jewelry to custom-made gifts. 

Dates: Dec. 17-18

1341 W. Randolph
West Loop

Roscoe Village Winterfest: Sleigh Rides and Santa

Have a festive weekend starting with a tree lighting, shopping at one-of-a-kind boutiques, hot chocolate galore, and holiday cider. On Sunday afternoon, bring the family for children’s activities, caroling, and, of course, Santa!

Dates: Dec. 3-4

Roscoe St.
Roscoe Village

Small Business Saturday in Lincoln Square/Ravenswood

Not only do many businesses in the area offer special discounts and promotions, but festive events take place throughout the day.  There are pictures with Santa, Victorian Carolers, and the annual Tree Lighting.

Dates: Nov. 26

Lincoln Square/Ravenswood

Southport Holiday Stroll & Cocktail Crawl

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!

Dates: Dec. 2

Southport Ave.

State Street Holiday Market

Support local Chicago artists and small businesses at the city's indoor version of Sundays on State. There will be weekly entertainment and seasonal activities.

Dates: Fridays-Sundays, Nov. 18-Dec. 18

35 S. State St.

Your daily dose of joy and connection
Get the Tinybeans app