Halloween falls on a Saturday in 2026. That lines up with two anniversaries on Broadway. The Aragon Ballroom is in its 100th year, and the Green Mill is marking 40 years under its current owner by bringing back its after-1 a.m. sets. Put those together and Uptown's entertainment district covers October 31 from a 3 p.m. show to a set that ends at 4 a.m. Sunday. The Uptown Theatre, the largest building in the district, opened to visitors on October 17 and 18 for Open House Chicago and is closed again for Halloween.
Saturday, October 31, in order
Here is the day as the venues have posted it:
- 3 p.m. to 5 p.m.: Paper Machete at the Green Mill.
- 8 p.m.: Doors open at the Riviera Theatre for Y2K: La Era del Perreo Halloween Edition, an 18-and-over reggaeton throwback dance party with Fulanito, Victor Cardenas and Don Chezina plus V5 DJs. The show starts at 9 p.m.
- 8 p.m. to midnight: Halloween Night with the Chicago Cellar Boys at the Green Mill.
- Evening: Gods of Chaos Halloween at the Aragon Ballroom.
- 1 a.m. to 4 a.m.: The Righteous Rooster Organ Trio's late set at the Green Mill, with a $5 cover from 1 a.m. to close.
Friday is close behind. The Green Mill's Halloween Eve with The Model Citizens runs 8 p.m. to midnight on October 30. Before that, Chris Foreman plays an early set from 5 p.m. to 7:15 p.m.
Why the night now goes to 4 a.m.
The last line of that list is new this year. On June 19, 1986, Dave Jemilo opened the current version of the Green Mill. The club marked the 40th anniversary this June by bringing back late-night music on Fridays and Saturdays. On Fridays, Marquis Hill leads the Green Mill Jam Session from 1 a.m. to 3:30 a.m. On Saturdays, the Chicago organ trio Righteous Rooster plays from 1 a.m. to 4 a.m.
The club's calendar still lists both late sets through the end of October. Each late set appears under the heading of the evening before it. So the Righteous Rooster set listed for Saturday, October 31, actually starts after the Cellar Boys finish and runs into the early hours of Sunday, November 1. The same goes for Friday: the Marquis Hill jam picks up after The Model Citizens close out Halloween Eve.
That makes Halloween night 2026 one of the longest single nights on the Green Mill calendar, roughly 13 hours from the afternoon show to the last organ chord.
A ballroom in its 100th year, and a movie palace still waiting for its second act
The Aragon's Halloween party lands in its centennial year. The Chicago Sun-Times dates the ballroom's opening to July 15, 1926. A building that has hosted Uptown nights for a century will host this one too.
The Uptown Theatre is the other centenarian on Broadway, and its story is going the other way. Block Club Chicago reported that the Chicago Architecture Center added the theater at 4816 N. Broadway to this year's Open House Chicago, held October 17 and 18. The building has been closed since 1981. It turned 100 last year, and the Architecture Center calls it the largest freestanding theater in North America. Theater developers Balaban and Katz built it as a movie palace with the architects Rapp and Rapp, in the Spanish Baroque Revival style. It later became a concert venue before it closed.
Adam Rubin, senior director of public engagement at the Architecture Center, described the interior to Block Club in July:
"So you're going to have terracotta ornament, you're going to have painted frescoes, you're going to have columns and coffers on the ceiling, and really a more is more mentality."
Rubin also called the Uptown an "incredibly endangered building type," expensive to maintain and to operate. According to Block Club's July coverage, a restoration is estimated at roughly $200 million, and the theater's reopening still depends on public funding that has not been settled.
So the biggest stage in the district gets two days of open doors, and the rest of October belongs to the Aragon, the Riviera and the Green Mill, all of them running full calendars right around it.
The weekend before belongs to Clark and Argyle
The week leading up to Halloween is quieter, but it has a closing night of its own. Black Ensemble Theater at 4450 N. Clark ends the run of You Can't Fake the Funk: A Journey Through Funk Music on Sunday, October 25. The ticket page lists five shows that final weekend: Friday, October 23, at 7 p.m., plus 2 p.m. and 7 p.m. on both Saturday and Sunday. According to BroadwayWorld's announcement of the run, tickets are $69 including fees.
That same Sunday, the costumes come out early on Argyle Street. The free Lanterns and Legends AAPI Market runs 3 p.m. to 8 p.m. on October 25 at Uni Uni + Haibayo, 1132 W. Argyle. AAPI Events Chicago is the organizer, and costumes are encouraged. The Chicago Asian Network listing describes the lineup as local artists, makers and food vendors.
Garuda, an Indonesian street-food restaurant at 1046½ W. Argyle, is a few blocks west of the market. Block Club reported in July that it opened in June. At the time, its Sunday hours ran 3 p.m. to 9 p.m., nearly the same window as the market. Hours can change after a restaurant's first months, so check before you walk over.
Black Ensemble's Saturday matinee and evening shows on October 24 also overlap with the Green Mill's late set that night. Righteous Rooster starts at 1 a.m. on Broadway, a few hours after the evening funk show on Clark lets out.
TimeLine's quiet stretch, and what fills November
TimeLine Theatre is the newest venue in the mix, and it sits out Halloween for scheduling reasons. The company held its ribbon-cutting at 5035 N. Broadway on March 21. The new building has a 250-seat theater, a gallery, rehearsal space, and a first-floor bar and café. Its fall show, The Birth of the Pill, closed October 11. The next production, Home, I'm Darling, runs November 11 through December 13.
TimeLine says the bar and café are open to the public. The hours it posted covered only the period through October 11, so check the TimeLine bar and café page for the weeks between shows before planning a pre-Halloween coffee there.
The concert calendars are already full past the holiday. The Aragon has Trippie Redd on Thursday, November 5, Jessie Reyez on November 16 and Victoria Monét on November 18. The Riviera has Pouya on November 5, Vince Staples on Sunday, November 8, and the Jayhawks on November 19. Both venues have shows on Thursday, November 5.
If you'd like a neighbor's view on which blocks of Broadway and Argyle fit your weekends, or on the Uptown homes within walking distance of the Green Mill and the Aragon, Cadence Realty is glad to help. Schedule a concierge consultation, and we'll talk about the parts of Uptown you already use and the ones still on your list.
