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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Robbie S.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 the organizer's own page still carries "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.
We publish what's sourced. As of late July 2026, the Northalsted Business Alliance had posted the date and the 29th-annual billing for 2026, but not the detailed schedule — the times, registration window and contest specifics still on its page describe the 2025 running.
So everything below marked (2025) is what happened last year, and it is the best available guide to what 2026 will look like. Halloween street events of this age rarely change shape year to year, but we're monitoring the official page and will update this guide the moment the 2026 schedule posts. Nothing here is invented.
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 2025 running went like this:
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 free and open to all ages, and contestants must be present to win.
Pro Tip
The sign-up window in 2025 was **6:30–7:30 PM** — a one-hour gate that closed an hour before the awards. If you're competing, treat 7:30 as a hard deadline and get there closer to 6:30. Chicago crowds bunch fast once the street closes.
The Group category is where Northalsted regulars put in real work — coordinated builds, rehearsed bits, sometimes a dozen people deep. If you're visiting and want to compete without a crew, Character and Creative are the realistic shots.
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 neighborhood's informal boundaries run Irving Park Road to the north, Broadway east, Wellington Avenue south and Sheffield Avenue west, overlapping Lakeview East. 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 roughly half a mile, so there's no bad stretch — but there are smarter ones.
Dress for a Chicago street in late October — highs in the mid-50s Fahrenheit, and it drops once the sun goes. The costumes that win are almost always the ones built to survive standing outside for three hours.
The parade ends at 10 PM. The night does not. Every bar on the strip runs a costume night, 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.
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Sidetrack is the anchor — a multi-room video bar with a rooftop deck, and the one place that reliably absorbs a parade-night crowd without feeling like a crush. Roscoe's Tavern is the other institution, with a dance floor and a long history of taking Halloween seriously. Hydrate is the late room: it runs latest on the strip and is where the night ends for most people still standing.
For something with more edge, Charlie's leans country-western with a late license, Progress Bar is the sleek dance option, and Splash brings the pool-party energy indoors. The Closet, a small lesbian-leaning stalwart at the Broadway end, and The North End, the neighborhood sports bar, are both good bets when the big rooms get impossible.
Pro Tip
On a Saturday Halloween the strip fills by about 10 PM and stays that way. If you want a specific bar, get in before the parade ends rather than after — the queue outside Sidetrack and Hydrate on a Halloween Saturday is a real thing.
Chicago's gay nightlife isn't only Halsted, and Halloween is a good excuse to see the rest of it.
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Cell Block is the leather bar on the strip itself; the Chicago Eagle and Jackhammer sit further north in Uptown and Rogers Park and run their own Halloween programming. Up in Andersonville — the city's other gay neighborhood, about fifteen minutes north — Atmosphere, Meeting House Tavern and The SoFo Tap make a quieter, more local alternative to the Halsted crush. Dorothy in Ukrainian Village is the cocktail-forward outlier and worth the trip on a normal night, less so when the parade is on.
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. Venue and set times firm up closer to the date.
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 is the one actually in Northalsted, steps from the strip. Best Western Plus Hawthorne Terrace sits just off 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.
Pro Tip
Halloween lands on a Saturday in 2026, which means the whole city is booked, not just the gay village. Northalsted has a genuinely small hotel inventory — book well ahead or plan on staying downtown and taking the Red Line up.
Take the train. Halsted closes for the parade, street parking in Lakeview is difficult on an ordinary night and effectively impossible on Halloween.
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.
Saturday, October 31, 2026 — Halloween night — on North Halsted Street in Northalsted (Boystown), Chicago. It's billed as the 29th annual edition. In 2025 the parade stepped off at 7:30 PM after a 6:30 PM registration window; the Northalsted Business Alliance hadn't published the detailed 2026 times as of late July.
In 2025 it started at Halsted & Belmont and finished at Halsted & Brompton, with the awards show in the lot at 3514 N. Halsted. That's a walk of roughly half a mile up the middle of the gay village. The 2026 route hadn't been separately confirmed at the time of writing, but it has run this stretch consistently.
Yes. Spectator admission is free and all ages, and entering the costume contest is free and all ages too. 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. In 2025, registration ran 6:30–7:30 PM at the registration tent with online sign-up also available, and contestants had to be present at the 8:30 PM awards show to win.
Sidetrack and Roscoe's Tavern are the two Northalsted institutions and both go all-out for Halloween; Hydrate is the late-night room. Charlie's, Progress Bar, Splash, The Closet and The North End fill out the strip, 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 is the hotel actually in Northalsted, 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 fills the whole city, and Northalsted's hotel inventory is small.
Take the CTA. The Red, Brown and Purple lines all stop at Belmont, two blocks from the parade start, and the Red Line stops at Addison for the north end of the route. Halsted closes for the parade and Lakeview street parking is very difficult on Halloween night, so driving is a poor plan.
