From Haunted Rooftops to Día de los Muertos

A rainy Halloween of concerts and costumes, then a week that pivots to Día de los Muertos.

By Raj Singh · Published October 31, 2026.

SATURDAY, OCTOBER 31

Allison Russell @ The Vic Theatre

Allison Russell is spending Halloween night at the Vic Theatre, bringing The In the Hour of Chaos Tour to town to celebrate her third studio album. The Grammy-winning singer-songwriter, poet and activist has built one of the more fiercely personal live shows going, and this is a headline stop — not a festival slot.

It's an all-ages show with a 7:30 PM start and opening support from Autumn Nicholas. If you'd rather trade the haunted-house line for something that actually moves you, this is the night.

Oktoberfest at Rainbow Beach

Out on the far South Side, the Chicago Park District is throwing a free Oktoberfest at Rainbow Beach Park from 11 AM to 3 PM. It's billed as a family-friendly community afternoon, but the pieces travel: a Trunk-A-Treat, a costume contest, plus food and music.

Admission is free and it's open to all ages. Come in costume, since there's a contest, and plan around the midday window — it wraps at 3.

Nightmare on Wacker Drive: Día de los Muertos @ LondonHouse

If your Halloween runs later and higher up, LondonHouse is transforming its 21st-floor lounge and its rooftop into a Día de los Muertos–themed party. A ticket buys a premium open bar from 9 PM to 1 AM and DJs all night, and there's a costume contest at midnight.

The prize is worth the effort: the winner gets an overnight stay at LondonHouse and two tickets to the hotel's New Year's Eve event. Tickets are $150, in the heart of the Loop.

DePaul Women's Soccer: Halloween at Wish Field

For a free, daylight alternative, DePaul's women's soccer team hosts St. John's at Wish Field in Lincoln Park, leaning into the holiday with themed music and costumes encouraged. Kickoff is 1 PM and admission is free — a rare general-audience sporting afternoon that costs nothing, and an easy stop on a Halloween Saturday.

THIS WEEK

Drop-In Sketching @ the Art Institute (Thu, Nov 5)

Come Thursday, the Art Institute hosts a drop-in sketching session from noon to 2 PM, inspired by its show Beatriz González: In Series and Full Color — more than 80 works spanning the Colombian artist's six-decade career, many on view for the first time. You sketch in the European painting galleries and take cues from González's prints and drawings. No registration, no experience required; materials are first-come, so bring your own sketchbook if you've got one. It's free with museum admission.

The Bewitching Hour @ Chicago Magic Lounge (Mon–Wed)

If Monday needs a lift, the Chicago Magic Lounge runs 'The Bewitching Hour' in its Performance Bar from 8 to 10 PM, Monday through Wednesday, with specially priced cocktails, featured wines, and close-up bar magic happening right at the bar. No reservations or tickets required — just turn up in Uptown, grab a seat, and let someone fool you with a deck of cards.

ON THE HORIZON

Ofrenda Sculptures Workshop @ Marquette Park (Mon, Nov 2)

As Halloween gives way to Día de los Muertos, the holiday's quiet heart is the ofrenda — the altar that welcomes back loved ones who've passed. On Monday, November 2, artist William Estrada leads a free, hands-on workshop at Marquette Park where everyone builds a small personal sculpture that joins a collaborative community altar.

It runs 5 to 7 PM and it's open to all ages, with materials limited and handed out first-come. If you do one thing this week beyond Halloween, make it this.