Recurring

Children’s Gingerbread House Decorating Party

Glessner House 1800 S. Prairie Avenue, Chicago

Be Your Own Architect! Come create a holiday masterpiece at Glessner House’s fourth annual Gingerbread House Decorating Party! Create your own mini gingerbread house to take home. All supplies are included. We’ll have lots of helpers, so no previous decorating experience is necessary. We’re offering two event times, 10:00-11:30am and 1:00-2:30pm. Select time at checkout. This event is recommended for…

$8.00 – $10.00

Christmas Market

Second Presbyterian Church 1936 S. Michigan Avenue, Chicago, IL

Handmade crafts, treats and Christmas gifts for sale.

Free

Holiday Tree Trimming

Cotton Tail Park 44 West 15th Street, Chicago, IL

Annual tree trimming at Cotton Tail Park.

Free

Sing Along Messiah

Second Presbyterian Church 1936 S. Michigan Avenue, Chicago, IL

Join us for our annual FREE Sing Along Messiah on Sunday, December 8th at 3:30pm featuring solos from professional singers in Chicago and accompanied by a chamber orchestra and our organ. The audience is invited to bring their own Messiah score to purchase one at the door. There will be a light reception in the Fellowship Hall following the performance.

Free

Brunch with Santa

Fatpour Tap Works 2206 S. Indiana Ave., Chicago, IL

Brunch and pictures with Santa. Reservations are recommended as this event fills up quickly!

South Loop Loft Walk

Grace Place 637 S Dearborn, Chicago

Join the South Loop Neighbors for this years Loft Walk with the "Deck the Halls" theme returning for the 2nd year! Get into the spirit of the season while enjoying holiday decor and warming stations along the way at local retail galleries and cafes! This highly anticipated event offers visitors a unique experience to see inside 8-12 urban residence and…

$30 – $40

Handel”s Messiah

Harris Theatre 205 E Randolph St, Chicago

December 14 @ 7:00 pm - 9:30 pm One of Chicago’s greatest holiday traditions, audiences flock to hear the thrilling renditions of Händel’s Messiah by the Apollo Chorus. This year we’re proud to announce a quartet of internationally-acclaimed soloists, including soprano Amanda Majeski, mezzo-soprano Kayleigh Decker, tenor William Hite, and bass-baritone Darren Stokes. Tickets are available now from Harris Theater.

Recurring

Christmas Candlelight Tour at Glessner House

Glessner House 1800 S. Prairie Avenue, Chicago

Christmas Candlelight Tours Sunday, December 15, 2019 4:30 PM 7:15 PM $15 per person / $12 for members Pre-paid reservations required PURCHASE TICKETS https://glessnerhouse.z2systems.com/np/clients/glessnerhouse/eventRegistration.jsp?event=885& These special 45-minute docent led tours will highlight Christmas customs and decorations of the late 19th century. The house will feature elaborate decorations of the period including a live tree decorated with period ornaments, toys and…

$12 – $15

Comedy Laugh Fest

Wintrust Arena 200 East Cermak Rd., Chicago, IL

Starring Cedric The Entertainer featuring D.L. Hughley, Eddie Griffin, Earthquake, & Deon Cole Ring in the New Year with laughter.

$49.00 – $129.00