The big light trails sell timed tickets, and the nights closest to Christmas go first, so a weeknight in late November or early December is the easiest way in. The tree lightings and window displays are free — and crowded, so get there early.
The State Street holiday windows and the Great Tree in the seventh-floor Walnut Room. Seeing them is free; lunch under the tree and Santaland visits need reservations.
More than 50 trees decorated by Chicago's cultural communities fill the Museum of Science and Industry, with displays on winter festivals of light. Included with admission.
A nighttime walking trail of large light installations set to music through the Chicago Botanic Garden in Glencoe. Timed tickets; popular nights cost more.
Scenes from the Joffrey Ballet's Nutcracker projected across theMART's facade, with Tchaikovsky's score along the Riverwalk. Free, Thursday to Sunday nights.
Lincoln Park Zoo lit up after dark, 4:30–9 p.m. Mondays are free with a reservation; other nights need a timed ticket, so buy ahead for weekends.
The city lights its official Christmas tree in Millennium Park at 6 p.m. Friday with a stage show, and a holiday market runs through the weekend. Free.
A daytime family festival, a 5:30 p.m. holiday parade down Michigan Avenue and fireworks over the river around 7:30. Free.
A decorated CTA train and bus with Santa aboard run on regular routes before Christmas. Find them on the CTA tracker and ride for a normal fare.
Andersonville lights its tree on Clark Street the same Friday as a menorah lighting and late shopping at the neighborhood's independent stores.
Beverly and Morgan Park's holiday shopping day: a free trolley up and down Western Avenue, kids' crafts, live music, food and drink specials and a scavenger hunt.
More this season: markets, skating, shows and New Year's Eve · Chicago holiday parades, 2026.
A few from Whosly's Chicago Cocktail Bars pack, each a short walk from one of the dates above.
The glass-topped rooftop of the Chicago Athletic Association hotel, looking over Millennium Park to the lake; in winter the terrace keeps fires going.
The Kimpton Gray's second-floor library bar in the Loop: leather chairs, nine versions of the old fashioned and a flight of drinks from cocktail history.
Lettuce's 1950s-style River North tavern, opened in 2025: 30 classic cocktails at fair prices and dipped sandwiches. A weekday 4-to-5 cocktail of the day is a steal.
An underground tiki bar reached down an alley off Hubbard, pouring rum drinks in elaborate mugs alongside pupu snacks. Bring a crowd for the Treasure Chest, a giant shared rum punch. The Bamboo Room inside is a separate tasting bar.
Every date and bar on this page. Tap a marker to see which it is.
Whosly's Chicago Festivals & Events list keeps every holiday date in Chicago and tells you when it matters.
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