Holidays in the Loop


It’s been quite a year. You deserve a joyful and safe holiday season. Thankfully, Chicago Loop Alliance has released their annual Holidays in the Loop guide, curating the very best of holiday festivities in Chicago. There are great options for everyone (many of which are free!), including PLENTY of outdoor socially-distanced activities, virtual experiences, shopping, and more! Check out the highlights of our favorite activities below, or view the full guide here.

Holiday Activities in the Loop

Art on theMART: The Joffrey Ballet’s “The Nutcracker”

When: Now through Dec. 31
Where: 222 W. Merchandise Mart Plaza

The Nutcracker presentation for Art on theMART, set to the music of Tchaikovsky’s beloved score. The performance runs nightly at 7 p.m. and 7:30 p.m., in partnership with Chicago’s Department of Cultural Affairs and Special Events. The projections — displayed on theMART’s 2.5 acre river-facade — can be viewed for free from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

Macy’s State Street holiday windows

When: Happening now
Where: 111 N. State St.

Since the early 1870s, Macy’s has been stunning spectators with its famed holiday window displays and celebratory events. Macy’s was the first store to feature holiday windows created for the pure fun and joy of the season and, with that, began a tradition that still lives on today. Be sure to go inside the store to see the Macy’s Christmas Tree, too—but don’t forget your mask!

City of Chicago’s 107th Christmas Tree

When: Now through Jan. 7
Where: Millennium Park, 201 E. Randolph St.

This year’s official lighting will take place virtually, but Chicagoans are encouraged to visit the festive site on their own. This year’s Tree is a 45-foot Blue Spruce donated by the family of Catherine Townsend of Chicago’s Morgan Park neighborhood (19th ward). Millennium Park holiday programs are produced by DCASE and presented by Powering Chicago, with support from the Millennium Park Foundation and Chicago Transit Authority.

Maggie Daley Park Skating Ribbon

When: Now through Feb. 28
Where: 337 E. Randolph St.

Come and skate the quarter mile Alpine inspired ice-skating ribbon, while taking in the magnificent views of the Chicago Skyline. Masks and reservations required.

Holidays in the Loop Painted Windows by Chicago Loop Alliance

When: Now through Jan. 8
Where: Various locations on State Street including theWit Hotel, StayPineapple Chicago, The Joffery Ballet, and 130 S. State St.

Chicago Loop Alliance has paired local artists with Loop businesses for a holiday window painting project. Enjoy beautiful artwork outside and at a safe distance. 

Macy’s Walnut Room

When: Now through Jan. 3
Where: 111 N. State St.

The Walnut Room reopened for Great Tree viewing and take-out orders on Nov. 7. Macy’s is offering the opportunity to bring the Walnut Room dining to your home through convenient, family-style takeout orders and meal kits. Limited reservations remain available for now through Jan. 3 on When indoor dining is permitted to resume, reservations will be required in advance. 

Experience Holidays in the Loop Virtually

Check out all the magic of Holidays in the Loop from the comfort and safety of your own home. This year’s virtual experiences include an online Christkindlmarket“The People’s Palace” Virtual Tours, Goodman Theatre’s “A Christmas Carol”, and Re-ACTIVATE – A Virtual Fundraiser to support the recovery of the Loop neighborhood. View all the virtual experiences here.

About Chicago Loop Alliance

Chicago Loop Alliance’s (CLA) mission is to create, manage and promote high-performing urban experiences, attracting people and investment to the Loop. CLA is a membership organization as well as the sole service provider for Special Service Area#1-2015, and the Chicago Loop Alliance Foundation produces public art projects and events.

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