Halloween lands on a Saturday this year, and Chicago is stretching it into a full week of costumes. Two parades bookend it, one marching north on Columbus Drive this Saturday and one turning 30 on Halsted Street on Halloween night. In between, Radius dresses up for two nights of Boots Halloween, ROOF on theWit runs away with the circus 27 floors above the Loop, and a mansion off the Magnificent Mile stages three nights of magic. Here is your Chicago Halloween 2026 nightlife guide for October 24 to November 7, starting with a fashion gala and a Lil Yachty show this weekend and ending with Kaskade and Carl Cox. Last week’s Halloween tickets and November galas guide has the full story on Death By Disco, House Calls and Hallo-Queen!, so those get a quick line here.
This weekend: ivory gowns, Lil Yachty and a parade in Grant Park
Runway LatinX, Saturday, October 24, and Sunday, October 25
The best-dressed room in the city on Saturday is CineCity Studios, 2429 W 14th St, where Runway LatinX 2026 stages Glam Reimagined, its main runway show and fashion gala. The dress code is Elegant Ivory. VIP doors open at 6 PM with a reception and pop-ups, general admission doors at 7 PM, and tickets start at $44.99 on Posh. On Sunday afternoon, from 2 to 5 PM, the weekend moves to 850 N Lake Shore Dr for RLX Couture Club, Living the Bella Vita, with a “Milano in Chicago” dress code, a trunk show by designer Nena Cavalieri and a panel on beauty and longevity.
Red Bull Setlist with Lil Yachty, Saturday, October 24
Down on Cermak Road, Radius Chicago hosts Red Bull Setlist featuring Lil Yachty, the show where the crowd has a hand in the songs. Doors are at 7 PM, it is 18 and over, and tickets are on AXS through Radius.
Arts in the Dark, Saturday, October 24
Before either of those, catch the free Arts in the Dark Halloween Parade, now in its 12th year, from 6 to 8 PM. Giant puppets, floats and costumed performers step off at Balbo Drive and march north on Columbus Drive with Buckingham Fountain behind them, and food trucks line the route. Come in costume and arrive early; the north end fills first.
Getting there this weekend: the CTA closes the elevated Loop tracks from 4 AM Saturday, October 24, to 4 AM Monday, October 26. Brown, Green, Orange and Pink Line trains stop short of the Loop, with shuttle buses filling the gaps, while the Red and Blue Line subways run as usual. Roosevelt on the Red Line is the easy stop for the parade.
Halloween weekend: three new parties to book
The big three from last week are still the backbone of Halloween weekend. Death By Disco fills Recess, City Hall and Morgan MFG on October 30 and 31, House Calls brings Skream all night to the Alhambra on Friday, and Hallo-Queen! takes over Metro and Smartbar on Sunday, November 1, from 9 PM. Smartbar’s own Hot B!T@# Halloween Party on October 31 is sold out. Three newer parties now deserve a spot on the list.
Boots Halloween at Radius, Friday, October 30, and Saturday, October 31
Radius, the giant club on Cermak Road, gives both Halloween nights to Boots. Friday belongs to Swedish rapper COBRAH, who plays her Gag Ball set, with Pixel Grip on a DJ set, Chicago house figure Shaun J. Wright, Kirk and BKHQ. Saturday brings London’s Bree Runway, deBasement, a Boots DJ set and the Pageant Queens, plus Daru b2b DJ Gaybash and Cryberbully. Expect drag, club kids and serious costumes. Doors are at 10 PM both nights, it is 21 and over, and tickets for Friday and Saturday are on AXS through Radius.
Circus After Dark at ROOF on theWit, Friday, October 30, and Saturday, October 31
ROOF on theWit, the glass-walled lounge 27 stories above State and Lake, turns into a big top for two nights. Circus After Dark promises glamour, mystery and mischief, theatrical moments and premium cocktails under the retractable roof, and guests are asked to dress to impress. Both nights start at 9 PM, it is 21 and over, tickets start at $27.25 on ROOF’s Halloween page, and tables are worth reserving for a group.
Haunted Halsted Fest and the 30th Halloween Parade, Saturday, October 31
The Haunted Halsted Halloween Parade turns 30, and Northalsted is celebrating with a full day. Haunted Halsted Fest opens at 11 AM on Halsted Street between Aldine and Addison, with free admission, local vendors, food, drinks, live music and street performers. At 7 PM comes Chicago’s only Halloween night parade, with more than 300 costumed marchers, fire performers from the Chicago Full Moon Jam, the Lakeside Pride Marching Band and the Windy City Rollers. The costume contest and post-parade party follow at 8 PM, with $4,000 in cash prizes across five categories. Details and contest registration are on Northalsted’s Halloween page.
More Halloween week nights worth dressing for
For something quieter and far more polished, The Hand & The Eye opens its Monarch Theater inside the McCormick Mansion, 100 E Ontario St, for The Grand Exhibition on October 27, 28 and 29: doors at 8 PM, an hour of seated magic at 8:30 PM and a welcome fall spritz, for $135 including tax. On October 31, a hundred years after Harry Houdini’s death, the mansion becomes The Midway of Wonders, with performances throughout and food and drink tickets included, from $325. Both are 21 and over, and tickets are on The Hand & The Eye’s booking page.
Prefer a circus with table service? Kermess runs Premonitions Inc. in its Belgian Spiegeltent on Floor 14 of 32 W Randolph St, with tickets from $89. In the West Loop, Spellbound turns City Winery, 1200 W Randolph St, into a five-room, three-stage Halloween party with a magician and fortune tellers from 8 PM to 3 AM on October 31; tickets are on Eventbrite.
Between parties, the city’s newer cocktail rooms make easy pre-game stops. Sip & Guzzle pours Thursday to Sunday at the Four Seasons’ Mile High Cocktail Club, Carlyle Club holds the river in the Reid Murdoch Building, the Champagne Room at the Ambassador keeps the coupes cold in the Gold Coast, Logan Inn anchors Logan Square, and The Lair waits under Stardust for the last drink. On Rush Street, Carmine’s has opened The Rush Inn, its first-floor lounge, with a daily 4 to 7 PM happy hour of martinis, spicy calamari and short rib sliders.
After the costumes: Kaskade, Carl Cox and the November calendar
Radius keeps the momentum going the next weekend. Kaskade plays Friday, November 6, and Carl Cox follows on Saturday, November 7, with Toman and Kidoo; doors are at 10 PM and both nights are 18 and over with a valid government ID. The season at Radius keeps rolling with Frost Children on November 12, Bonobo on November 25 and Ben Klock’s Photon on November 27.
The gala calendar picks up in the same stretch. BET tapes the Soul Train Awards at the Harris Theater on Thursday, November 5, and the 25th PAWS Chicago Fur Ball fills The Drake on Friday, November 13; last week’s November galas guide has the details on both.
Opening soon: three rooms on the radar
Three nightlife rooms are getting close, and none has announced an opening date. In the West Loop, A Ma Maniere is bringing a lounge with an outdoor patio to 1144 W Washington Blvd. In Fulton Market, Osaka Nikkei is preparing 1101 W Lake St with Kero Bar, a cocktail lounge with weekend DJs. And in River North, The Lake at 205 W Superior St is taking shape as a five-story private members’ club with restaurants, cocktail bars and a roof terrace.
Your Halloween week at a glance
- Sat Oct 24: Runway LatinX at CineCity Studios, VIP 6 PM, GA 7 PM, from $44.99
- Sat Oct 24: Arts in the Dark Halloween Parade, Columbus Drive, 6 to 8 PM, free
- Sat Oct 24: Red Bull Setlist with Lil Yachty, Radius, doors 7 PM, 18+
- Sun Oct 25: RLX Couture Club, 850 N Lake Shore Dr, 2 to 5 PM
- Tue Oct 27 to Thu Oct 29: The Grand Exhibition, The Hand & The Eye, 8:30 PM, $135
- Fri Oct 30: Boots Halloween with COBRAH at Radius, 10 PM, 21+; Circus After Dark at ROOF on theWit, 9 PM, from $27.25
- Sat Oct 31: Haunted Halsted Fest from 11 AM, parade at 7 PM, costume contest at 8 PM
- Sat Oct 31: Boots Halloween with Bree Runway at Radius; Circus After Dark at ROOF; Spellbound at City Winery; The Midway of Wonders, from $325
- Sun Nov 1: Hallo-Queen! at Metro and Smartbar, doors 9 PM
- Fri Nov 6: Kaskade at Radius, 10 PM, 18+
- Sat Nov 7: Carl Cox at Radius, 10 PM, 18+
Frequently asked questions
Where should I go out for Halloween in Chicago in 2026?
For a big club night, Boots Halloween at Radius runs October 30 and 31 with COBRAH and Bree Runway. Circus After Dark at ROOF on theWit offers a dressier rooftop party both nights from $27.25, and the free Haunted Halsted Fest and 30th Halloween Parade fill Halsted Street on Saturday, October 31, 2026.
What time is the 2026 Northalsted Halloween Parade in Chicago?
The 30th Haunted Halsted Halloween Parade steps off at 7 PM on Saturday, October 31, 2026, in Northalsted. Haunted Halsted Fest opens at 11 AM on Halsted Street between Aldine and Addison with free admission, and the costume contest and post-parade party start at 8 PM.
How much are tickets to Circus After Dark at ROOF on theWit?
Tickets to Circus After Dark at ROOF on theWit start at $27.25. The Halloween party runs Friday, October 30, and Saturday, October 31, 2026, from 9 PM in the rooftop lounge above the Loop, it is 21 and over, and guests are asked to dress to impress.
When is the Arts in the Dark Halloween Parade in 2026?
The 12th Arts in the Dark Halloween Parade is Saturday, October 24, 2026, from 6 to 8 PM. It is free, steps off at Balbo Drive and marches north on Columbus Drive in Grant Park. The CTA closes the elevated Loop tracks that weekend, so the Red Line to Roosevelt is the easiest ride.
Is Boots Halloween at Radius Chicago 21 and over?
Yes. Boots Halloween at Radius Chicago, 640 W Cermak Rd, is 21 and over on both nights. Friday, October 30, 2026, features COBRAH, Pixel Grip and Shaun J. Wright, and Saturday, October 31, features Bree Runway, deBasement and the Pageant Queens, with doors at 10 PM and tickets on AXS.
When do Kaskade and Carl Cox play Radius Chicago?
Kaskade plays Radius Chicago on Friday, November 6, 2026, and Carl Cox follows on Saturday, November 7, with Toman and Kidoo. Doors are at 10 PM both nights, both shows are 18 and over with a valid government ID, and tickets are on AXS through the Radius website.
Further reading
- Runway LatinX 2026 tickets on Posh
- Red Bull Setlist with Lil Yachty at Radius
- Arts in the Dark Halloween Parade
- CTA Loop and Lake junction weekend service changes
- Boots Halloween at Radius, Friday
- Boots Halloween at Radius, Saturday
- Circus After Dark at ROOF on theWit
- Haunted Halsted Halloween Fest and Parade
- The Hand & The Eye: The Grand Exhibition and The Midway of Wonders
- Spellbound at City Winery
- Kermess: Premonitions Inc. tickets
- Carmine’s Chicago and The Rush Inn
- Radius Chicago calendar
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