Goth Happy Hours and a Halloweekend Warm-Up

Your daily guide to what's popping in Chicago

By Raj Singh · Published October 29, 2026.

THURSDAY, OCTOBER 29

Golden Hour Featuring Philly Peroxide @ Epiphany Center for the Arts

Your happy hour just got darker. Epiphany Center for the Arts hands the decks to DJ Philly Peroxide — a fixture of Chicago's dark-alternative nightlife since 2009 and the host of the long-running Bittersweet goth night — for a free DJ set paired with food and drink specials. Expect it to lean breakbeat, dub and psychedelic, so think a goth-flavored wind-down rather than a straight dance floor.

The set starts at 5PM and it's free — a come-wind-down-from-work or start-the-night-early kind of evening, and an easy, no-cover way to kick off Halloweekend in the West Loop.

A Night with Xscape, Plies, Case, Pleasure P, and Ann Marie @ The Chicago Theatre

Five acts, one marquee: Xscape, Plies, Case, Pleasure P and Ann Marie all share the bill at The Chicago Theatre tonight. It's a multi-artist throwback night where the lineup is the whole pitch — if those names mean something to you, you already know whether you're going. Showtime is 8PM at 175 N State St in the Loop. Ticket prices weren't in our listing, so check the link before you head down.

Chicago Astronomer at Northerly Island

The Chicago Astronomer sets up professional-grade telescopes at Northerly Island for a free, guided stargazing session — the Park District calls it its premier astronomy series, pairing a short presentation on what's visible that night with hands-on telescope time. It's pitched at beginners and enthusiasts alike, it's all ages, and it's free.

Sessions run 6:30 to 8:30 PM. One honest caveat straight from the listing: these happen weather permitting, so check the forecast before you head over — tonight's reading overcast.

America@250: Now Is the Time @ Court Theatre

Court Theatre in Hyde Park anchors America@250 — Now Is the Time: Artists Go to Work, a curated run of exhibitions, performances and artist-led discussions responding to the country's 250th anniversary and Toni Morrison's charge that 'this is precisely the time when artists go to work.' It's framed around reckoning with founding ideals and the stories a nation chooses to face, and the source says all events are open to the public. The program runs daily through December 20, so tonight is one entry point rather than a one-off.

FRIDAY, OCTOBER 30

Montrose Monster Mash @ Montrose Avenue

Halloween Eve belongs to the kids and candy-hunters along Montrose Avenue. The annual Montrose Monster Mash turns the Montrose-and-Broadway stretch into a trick-or-treat route, with local shops and restaurants handing out candy for what the organizers — the Greater Ravenswood Chamber of Commerce — call a spirited night of spooky fun.

It's free and kicks off at 4PM Friday; the listing notes there's no cost but encourages registering online in advance. Easiest approach is the Red Line to Wilson.

BOGO Fridays @ Smack Dab

Smack Dab, the Edgewater brunch spot on North Clark, runs a rotating buy-one-get-one special every Friday — some weeks it's sandwiches, some weeks drinks or pastries, and they keep what's on deck under wraps (join their email list for the heads-up). The deal window runs 8 AM to 2 PM. Which items are BOGO this week isn't something our listing spells out, so go in flexible — a low-commitment way to start a Friday in Edgewater.

THIS WEEK

Hot Chocolate Run @ Millennium Park

The Hot Chocolate Run lands in the Millennium/Grant Park area downtown on Sunday — the annual race (and walk) that rewards you with a spread of chocolate at the finish. Time Out notes participants get a race-themed hoodie, a medal shaped like a cup of hot cocoa, and access to a post-race gathering where chocolate goodies are served.

Registration starts at $59, and with the race just days out it's a now-or-never sign-up. Transit's easy: the listing points to the Red Line to Monroe, or the Loop lines to Randolph.