On Saturday, Nov. 7, at noon, a 45-foot tree lights up in the Walnut Room at Macy's on State Street. It is the 119th time the store has done it. The celebration runs on the store floor from noon to 5 p.m. Outside on State Street, nothing changes yet. Daley Plaza is still a plaza, and the Millennium Park rink is still empty.
That changes thirteen days later. On Friday, Nov. 20, the Christkindlmarket, the city's tree, the McCormick Tribune Ice Rink and two new things on Macy's seventh floor all open together. Last year they didn't. Macy's is the reason, and the change says a lot about where the Loop's holiday season now starts.
Saturday, Nov. 7, Happens Indoors
The first opening belongs to Macy's State Street at 111 N. State St. Santaland opens Nov. 7, the same day as the Great Tree lighting. Reservations opened Oct. 31. Macy's says it releases Santa time slots seven days before each visit, so a booking for Thanksgiving week can't be made until the week before.
The Walnut Room's holiday menu and Great Tree display also start Nov. 7. The Walnut Room's own page says they run through Sunday, Jan. 17, 2027, and lists Great Tree breakfasts. Macy's general Chicago holiday page still shows an earlier end date of Jan. 10. Of the two, the restaurant's page is the one to trust.
Choose Chicago lists the store's holiday windows as opening in November 2026, without a specific day.
So the first weekend is mostly a single building with a single tree. Neighbors who want the Walnut Room without the full crowd have a two-week window before Nov. 20.
The Date That Moved
Macy's opened its first Chicago Holiday Square in 2025. It's a market run with Bensidoun USA, a company that operates French open-air markets. In its September 2025 announcement, Macy's said the State Street market would run Nov. 26 through Dec. 24. That was its debut, and it opened after the Christkindlmarket had already been going for days.
This year, Holiday Square opens Friday, Nov. 20, on Floor 7. Macy's calls it a French-inspired holiday market of food and gifts drawn from Chicago's neighborhoods. The vendors listed so far are:
- Dreams Candles
- La Boulangerie & Co
- OrPerlé Jewelry
- Printed Canvas
- Smashing Jewels
- Spanish Stoneware
- Tori Grace Outfitters
- Wearable Wellness
- Chef Pam's Pasties
The Holiday Square page lists hours of 10 a.m. to 6:30 p.m. and a 2 p.m. close on Christmas Eve. The State Street store page says the market is open Thursdays through Sundays, so check the day before planning a weekday visit. The Frango Cafe also reopens on Floor 7 the same Friday, serving Frango hot cocoa, a holiday Poinsettia cocktail and Frango coffee. Frango chocolates are sold on Floors 1, 5 and 7.
Moving Holiday Square from Nov. 26 to Nov. 20 means the busiest store in the Loop now opens its holiday market on the same day as the busiest plaza in the Loop, six days before Thanksgiving instead of the day before it.
Everything That Opens Friday, Nov. 20
The Christkindlmarket started in 1996 and turns 30 this year, at the same Daley Plaza location. Here is everything that starts that Friday within walking distance of State Street.
| What | Where | Hours | Runs Through |
|---|---|---|---|
| Christkindlmarket, 30th year | Daley Plaza, 50 W. Washington St. | Regular hours 11 a.m.–9 p.m. Fri–Sat, 11 a.m.–8 p.m. Sun–Thu; 11 a.m.–4 p.m. on Thanksgiving and Christmas Eve | Dec. 24 |
| City tree lighting | Millennium Park, stage on Washington St. | Ceremony at 6 p.m. | Tree lit through Jan. 10, 2027 |
| McCormick Tribune Ice Rink | Millennium Park | 11 a.m.–10:30 p.m. daily, free | February 2027, weather permitting |
| Holiday Square | Macy's, Floor 7 | 10 a.m.–6:30 p.m., Thursdays–Sundays per the store page | Christmas Eve, closes by 2 p.m. |
| Frango Cafe reopening | Macy's, Floor 7 | Hours not yet posted | Not yet posted |
The city's tree ceremony ends with fireworks, and the stage is set up on Washington Street. Admission to the rink is free. The city says reservation details will be posted later.
At the market, Block Club Chicago reported that Avondale's DMen Tap will sell German-style döner kebabs from a booth decorated with Krampus themes. Chiya Chai, which has locations on the Riverwalk and in the Loop, will sell food, drinks and gifts from Nepal. Choose Chicago's guide also lists Rollmops fish, pierogi, raclette and pumpkin-spice chai, along with the usual hot chocolate and cider.
For the anniversary, the market's merchandise lineup includes a pearl-white, flute-shaped 200-milliliter mug with a market scene and fireworks, a green Christmas-tree mug and an anniversary beer stein. The Mini Stein Shot Cup is new this year. There's also a snow-globe-style ornament and a Krampus stuffie with a new look for 2026.
The Eight Days Between Nov. 19 and Thanksgiving
The Nov. 20 opening is the middle of a tight run of events. Here is the order:
- Thursday, Nov. 19. "The Night Before Christkindlmarket," a ticketed preview at Daley Plaza with early access, vendor conversations and live holiday entertainment. Leila Schmidt of German American Events told Block Club Chicago that "our preview party will be extra special this year."
- Friday, Nov. 20. The market, the tree, the rink, Holiday Square and the Frango Cafe all open.
- Saturday, Nov. 21. The Wintrust Magnificent Mile Lights Festival. The parade runs on Michigan Avenue from Oak Street to Wacker Drive at 5:30 p.m., with fireworks at 7:15 p.m.
- Thursday, Nov. 26. The Chicago Thanksgiving Parade runs on State Street from Ida B. Wells Drive to Randolph Street, 7:45 to 10 a.m. The Christkindlmarket is open 11 a.m. to 4 p.m. that day.
The parade route ends at Randolph, one block north of Daley Plaza and right by Macy's. In 2025, Holiday Square opened the day before Thanksgiving. This year it will have been open almost a week by the time the parade reaches it.
Getting to Daley Plaza With State/Lake Closed
Two of the train stops closest to all this have changed since last December. The elevated State/Lake station has been closed for demolition and reconstruction since Jan. 5. Brown, Green, Orange, Pink and Purple Express trains skip it. The Chicago Loop Alliance points riders to Clark/Lake or Washington/Wabash instead. The Red Line subway station at State and Lake is still open, and State Street buses still run. For Daley Plaza, Clark/Lake is the closer of the two alternatives. For the Walnut Room and Millennium Park, Washington/Wabash is closer.
Reconstruction of the Lake Street Bridge has been disrupting Green and Pink Line service into the Loop since Oct. 13. As of Block Club Chicago's Oct. 28 report, Green Line trains were running in two sections split at Clinton and Clark/Lake, with shuttle buses between them, and Pink Line trains were not running in the Loop. The same report says another two-week Green and Pink outage is planned for spring. Check the CTA's alerts before Nov. 20 if either line is part of your route.
On Michigan Avenue, the Chicago Department of Transportation started installing a northbound bus-only lane between Roosevelt Road and Wacker Drive in late September. Block Club Chicago reported that the striping and sign work would take seven to 10 days. This will be the first holiday season with that lane on the street that leads north toward the Lights Festival route.
After the First Week, the End Dates Spread Out
The season opens on one Friday, but it closes over about three months. The Christkindlmarket and Holiday Square both end on Christmas Eve. The city tree stays lit through Jan. 10, 2027. The Walnut Room's Great Tree stays up through Jan. 17. The rink is scheduled to stay open into February, weather permitting.
For anyone who lives within a few blocks of Washington Street, that means a crowded stretch from Nov. 19 to Christmas Eve. After that, the tree, the Walnut Room and a free rink stay open into January and February, and the crowds have mostly gone.
Living a short walk from Daley Plaza in late November is part of what a Loop address is worth. When it's time to put a number on yours, Millie Rosenbloom prices Loop condos building by building, with the foot traffic and transit changes on your block factored in. Get a Free Home Valuation.
