Part of the Gay Chicago Guide — bars, events & things to do.
Saturday, October 31, 2026
The circuit parties, afterhours and official events happening across Haunted Halsted Halloween Parade in Chicago — dates, venues and tickets.
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Halloween in Chicago has a center of gravity, and it's a half-mile of North Halsted Street. The Haunted Halsted Halloween Parade is the Northalsted Business Alliance's Halloween-night street party — a costume parade straight up the spine of the city's gay village, with a contest, real prize money, and a few thousand people in the street watching. It is free, it is outdoors, and it is the reason Chicago's gay neighborhood is where you want to be on October 31.
Pro Tip
October 31, 2026 falls on a Saturday. Worth saying plainly, because some listings still carry "Friday, October 31" — that was 2025. A Saturday Halloween is the best possible draw for a street parade, and it means the bars will be at full tilt both the night of and the night before.
For the parade's 30th anniversary, the Northalsted Business Alliance has turned Halloween into an all-day affair. From 11 AM the Haunted Halsted Fest takes over North Halsted as a pedestrian-only block party, with food and drinks, local vendors, live music and street performers, a kids' zone and daytime trick-or-treating at Halsted businesses. At 6 PM the street is cleared to the sidewalks so the parade can set up.
The parade lineup so far includes the Lakeside Pride Marching Band, the Chicago Thriller Flash Mob, Chicago Spirit Brigade, the Windy City Rollers, decorated vehicles from the Windy City Jeep Club, and a pyrotechnic finale from Full Moon Jam's fire performers. Featured appearances and the live-performance lineup were still listed as "coming soon" on the organizer's page as of October 8.
The parade is short, dense and entirely about the costumes. There are no floats to speak of and no ticketed grandstand — it's a march up Halsted with the crowd pressed to both curbs, and then an awards show at the end.
The 2026 schedule, per the Northalsted Business Alliance:
The costume contest is the main event, and the prize money is not token. Five categories — Character, Creative, Scary, Youth (under 13) and Group — each paying $500 for first, $200 for second and $100 for third. That's $4,000 in total prizes. Entry is $5 and open to all ages, and contestants must be present to win.
Pro Tip
The organizer strongly encourages signing up online in advance. Day-of entries are taken from 2 PM at the costume registration tent at 3211 N. Halsted, on the east side of the street, and bib check-in closes at 6:15 PM. The parade goes on rain or snow.
One piece of fine print: the organizer's category list says Group awards only one prize, even though the headline promises three places in every category. If you're visiting without a crew, the solo categories are Character (media, pop culture, celebrity, history), Creative (originality, materials, wow factor) and Scary.
Some context for why a neighborhood parade carries this much weight.
Northalsted — still called Boystown by most people who live there — holds the distinction of being the first gay village in the United States officially recognized by a big-city government. That recognition came with money: in 1998, a $3.2 million streetscape project under Mayor Richard M. Daley erected the rainbow pylons that still line Halsted Street. Twenty-odd art-deco columns, ringed in rainbow bands, marking the district in a way no American city had done before.
Since 2012, the Legacy Project has been mounting commemorative bronze plaques on those pylons, turning the street into an outdoor museum of LGBTQ+ history. You walk past them on the parade route without necessarily noticing — but that's what the costumes are marching through.
The heart of it is North Halsted between Belmont and Grace, the stretch the pylons mark, inside the wider Lakeview East area. The business district formally adopted the Northalsted name in 2020; in practice, both names are in daily use, and nobody will blink at either.
Pro Tip
The rainbow pylons are the easiest orientation tool in the neighborhood. If you can see them, you're on the strip. The parade route runs between two of the busiest stretches — Belmont at the south end, Brompton up near Wrigleyville.
The route is under half a mile, so there's no bad stretch — but there are smarter ones.
Dress for a Chicago street after dark in late October: the parade starts at 7 PM and goes on rain or snow. Build a costume you can stand outside in for a few hours.
The contest and party wrap at 10 PM. The night does not: the organizer promises Halloween happenings in venues along Halsted all night long, and the strip is walkable end to end — this is the rare gay Halloween where you never need a car or a cab between venues.
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Sidetrack is the anchor — a sprawling multi-room video bar with a rooftop deck, open until 3 AM on Saturdays. Roscoe's Tavern is the other institution, with a dance floor. Hydrate is the late room, open until 5 AM on Saturdays: resident DJ Isis Muretech has its Halloween night, and earlier that week it hosts the Creature of the Night Pageant. Two more rooms on the route tie their night to the parade: Replay throws an all-day Multiverse of Madness parade party with its own costume contest, and Kit Kat Lounge, a few doors from the contest lot, streams the parade live to the 6 PM seating of its Villains Halloween Ball drag dinner.
Over on Broadway, a couple of blocks east of Halsted, Charlie's leans country-western and stays open until 5 AM on Saturdays, and The Closet, a small bar open since 1978, sits just north of Belmont. Progress Bar and Splash are both on the 3300 block of Halsted, and The North End, the neighborhood gay sports bar just north of Addison, is a good bet when the big rooms get impossible.
Pro Tip
Halsted is cleared to the sidewalks at 6 PM to set up the parade, so the daytime fest crowd and the parade crowd merge behind the barricades from then on. If you want a specific bar, get in before the parade ends rather than after.
Chicago's gay nightlife isn't only Halsted, and Halloween is a good excuse to see the rest of it.
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Chicago, Illinois
Cell Block is the leather bar on Halsted itself. The Chicago Eagle is further north in Uptown, and Jackhammer in Rogers Park has its Primal Halloween Howl on the night. Up in Andersonville — the city's other gay neighborhood, a couple of miles north along Clark Street — Atmosphere, Meeting House Tavern and The SoFo Tap make a quieter, more local alternative to the Halsted crush; The SoFo Tap's GRRR: A Nightbear on Clark Street lands the night before. Dorothy in Ukrainian Village bills itself as Chicago's lesbian bar and has its own Halloween Night with MobeeThicc.
One circuit option is already on the calendar for Halloween night itself: BRÜT Chicago — Halloween, the touring underground party founded in New York in 2013, with DJs Dan Darlington and Matt Suave from 9 PM to 3 AM at 619 Howard St, on the Chicago–Evanston line.
Staying in Northalsted or Lakeview means you walk home from the parade, which on Halloween night in Chicago is worth more than a nicer room downtown.
City Suites, on Belmont by the 'L' stop, is the closest to the parade start. Best Western Plus Hawthorne Terrace sits on Broadway in Lakeview and is the reliable mid-range pick. The Willows and The Majestic are the quieter Lakeview East options — residential streets, short walk to Halsted. If those are gone, Hotel Zachary and the Chicago Hotel Collection put you in Wrigleyville, one Red Line stop north of Belmont.
Pro Tip
Halloween lands on a Saturday in 2026, so expect the whole city to be busy, not just the gay village. Book early, or plan on staying downtown and taking the Red Line up to Belmont.
Take the train. Halsted is closed to traffic between Belmont and Addison from 10:30 AM on Halloween until 2 AM, and parking is banned on Halsted and the nearby side streets from 7 AM, with towing.
With Halloween on a Saturday, the sensible shape is a Friday arrival, the parade and the strip on Saturday, and a slow Sunday. Andersonville is the right call for the recovery day — brunch, bookshops and a much gentler pace than Halsted.
If you're building a longer Chicago trip, our guide to the best gay bars in Chicago maps the whole scene, and Northalsted Market Days is the same neighborhood's August blowout — the other date worth planning a trip around.
Chicago is one of twenty cities on our national list. Gay Halloween 2026: the best parties by city covers the other marquee weekends, from West Hollywood Carnaval to Spooky Bear in Provincetown.
Saturday, October 31, 2026 — Halloween night — on North Halsted Street in Northalsted (Boystown), Chicago. It's the 30th annual parade: the Haunted Halsted Fest runs from 11 AM, the parade steps off at Halsted & Belmont at 7 PM, and the costume contest and post-parade party run 8–10 PM.
It starts at Halsted & Belmont and finishes at Halsted & Brompton, with the costume contest and post-parade party in the NoHa parking lot at 3514 N. Halsted. That's a walk of under half a mile up the middle of the gay village.
Watching is free and all ages, and so is the daytime Haunted Halsted Fest. Entering the costume contest costs $5, open to all ages. The bars along the route set their own covers on Halloween night, which is where you'll actually spend money.
There are five categories — Character, Creative, Scary, Youth (under 13) and Group. Each pays $500 for first place, $200 for second and $100 for third, for $4,000 in total prizes. Entry is $5: register online in advance, or on the day from 2 PM at the registration tent at 3211 N. Halsted, with bib check-in until 6:15 PM. Finalists go on stage at the 8 PM contest at 3514 N. Halsted, and contestants must be present to win.
Sidetrack and Roscoe's Tavern are the two Northalsted institutions, and Hydrate is the late room, open until 5 AM on Saturdays. Charlie's, Progress Bar, Splash, The Closet and The North End fill out the strip and nearby Broadway, all within a walk of the parade route. For leather, Cell Block is on Halsted itself, with the Chicago Eagle and Jackhammer further north.
City Suites, on Belmont by the 'L' stop, is the closest hotel to the parade start, with Best Western Plus Hawthorne Terrace, The Willows and The Majestic nearby in Lakeview. Hotel Zachary and the Chicago Hotel Collection in Wrigleyville are one Red Line stop north. Book early — a Saturday Halloween keeps the whole city busy.
Take the CTA. The Red and Brown lines stop at Belmont, about a block and a half west of the parade start, and the Red Line stops at Addison for the north end of the route. Halsted is closed to traffic between Belmont and Addison from 10:30 AM to 2 AM, with towing on Halsted and nearby side streets, so driving is a poor plan.
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