Chicago Holiday Events Guide

The city's own official tree goes up in Millennium Park — not to be confused with the Magnificent Mile Lights Festival the night before.

A Merry Makers Market leads into a 5 PM countdown with the mayor, Santa, and the Palatine Children's Chorus.

The North Shore's own kickoff to the winter season, confirmed ahead of several nearby-suburb lightings that hadn't locked a date yet.

Confirmed on the village's own 2026 calendar — Santa, marching band, choral society, and a tree strung with resident-made ornaments.

Already on the Des Plaines History Center's own 2026 calendar — food trucks, live stage performances, and community-decorated trees.

Santa shares the bill with Chicagoland Greek-school students singing carols and the karavákia illuminated boats lighting up storefronts.

Dating back to 1926 — the area's oldest tree lighting, paired with a Free Family Fun countdown at Harmony Park and Dickensian-costumed trolleys.

Caroling at the Al Larson Prairie Center for the Arts spills next door, where Santa arrives by fire truck to light the tree.

A Wednesday-before-Thanksgiving tradition pairing the tree lighting with a scaled-down indoor Christkindlmarket.

60 years running — Santa's arrival, a tree lighting on the Memorial Building lawn, a kiddie train and carousel.

Chicago's original German Christmas market turns 30 this year — wooden chalets, Glühwein, ornaments, and food stalls.

A fifth-floor-ballroom indoor German Christmas market — Glühwein, holiday vendors, Santa photos.

33 years running — thousands of homemade cookies sold by the pound alongside local crafters and a Santa visit.

100–200 artisans on Thanksgiving weekend's 'Small Shop Saturday,' dog-friendly.

The Puerto Rican Cultural Center's Día de Los Reyes toy drive and celebration — the date itself is fixed by the holiday every year.

A full week of free daily programming through all seven Kwanzaa principles, plus a Black-owned-vendor marketplace.

A candlelit procession from the museum to an evening program at Ebenezer Lutheran Church, tied to the actual Dec. 13 feast day.

A pre-dawn 9-day Mass novena into Christmas Eve, rooted in a centuries-old Filipino Catholic tradition, across dozens of parishes.

A 31-foot menorah lit in the middle of the Loop, with live music and hot holiday snacks, right next to Christkindlmarket.

A nightly lighting with Chabad of Skokie turning the mall's center court into the neighborhood's Hanukkah gathering spot.

An indoor amusement park under one roof, ice rink included with admission, expanded with more rides this year.

Fifty-plus trees, each decorated by a different Chicago cultural or immigrant community group, filling the museum's Great Hall.

Six decorated railcars and an open flatcar carrying Santa's sleigh — no special ticket, just catch it on your regular commute.

18 years in — over 2,200 runners through the Beverly Hills area's own streets on Thanksgiving weekend.