Chicago Nightlife Oct 17 to Nov 1: Halloween Tickets & Galas

Two weeks separate Chicago’s opening rush from Halloween weekend, and this is the stretch to plan. A spiegeltent cabaret and North America’s No. 1 bar opened on the same Thursday and are settling into their first full weekends. Halloween falls on a Saturday this year, so the costume parties run Friday, Saturday and Sunday, and the best tickets are moving now. Behind that, November’s gala season is already taking shape, from the Soul Train Awards coming home to the Harris Theater to a black-tie night with dogs at The Drake. Here is your Chicago nightlife plan from October 17 to November 1, with the dates to lock in and a few nights worth dressing up for.

Just opened: start with the two new rooms

A Sip & Guzzle bartender garnishing a fall apple cocktail in a coupe — A bartender finishes one of Sip & Guzzle’s fall apple cocktails in New York. Photo: @sipandguzzlenyc on Instagram (photographers @by__dre and @ericmedsker).

Begin 46 floors above the Gold Coast. Sip & Guzzle Chicago has taken over the Mile High Cocktail Club at the Four Seasons Hotel Chicago, pouring Thursday to Sunday from 5 to 10 PM through March 14, 2027. Every seat is $85 and covers two cocktails, and reservations are on OpenTable. Book an early seating and you get the lake going dark from one of the highest bars in the city.

Then take a cab south to Randolph Street, where Kermess Chicago runs Premonitions Inc. inside a century-old Belgian Spiegeltent on Floor 14 of 32 W Randolph St. The show runs about 90 minutes, it is 21 and over, and seats are Classic $89, Preferred $119 or VIP $149 on kermesschicago.com, with food and drinks ordered separately. Curtain is 7:30 PM on Fridays and Saturdays, with Sunday shows earlier in the day, and there are shows on Friday, October 30, and Saturday, October 31, which makes the velvet tent an easy Halloween date for anyone skipping the costume crowds.

Saturday, October 17, is also the night of the Field Museum Gala, the season’s flagship black-tie party, in Stanley Field Hall. For a later, louder Saturday, TAO Chicago at 632 N Dearborn St hosts Gordo x Metro B2B from 10 PM to 4 AM, a back-to-back set that runs until close. It is 21 and over, the dress code is smart casual (no shorts, caps or athletic wear), and general admission starts at $22.40 with fees on TAO’s ticket page, with VIP table shares at $168.

Your rooms for the weeknights in between

The fall openings that set the tone in September are now easy weeknight plans. On the river, Carlyle Club fills the landmark Reid Murdoch Building at 316 N Clark with a steakhouse grill, a sushi counter and river windows behind the bar. For a coupe before dinner, the Champagne Room at the Ambassador pours Moët in the Gold Coast. Logan Inn turns cafe mornings into cocktail nights on a Logan Square corner, and The Lair waits under Stardust at 710 N Clark for the last drink of the night.

Planning daytime and dinner plans for the next ten days too? Our weekend and next week guide covers the film festival, Open House Chicago and the Celebrity Chef Ball. If you missed last Friday’s edition, our October 10 to 18 nightlife guide has the Field Museum Gala and the full opening-night story.

Saturday, October 24: Lil Yachty at Radius

Red Bull Setlist makes its U.S. debut at Radius Chicago, 640 W Cermak Rd, with Lil Yachty on stage for a show where the crowd helps shape the setlist. Doors are at 7 PM and it is 18 and over, so it works for a mixed-age group of friends before a Pilsen late night. Tickets are through Radius.

Halloween weekend: the tickets to book now

Two performers in matching blue dresses holding a Death By Disco sign in a hotel hallway — Death By Disco, Thank You For Dancing’s Halloween party. Photo: @thankyoufordancing on Instagram.

Halloween on a Saturday means Friday, October 30, is a real party night and Sunday, November 1, is the city’s best excuse for one more. Three tickets stand out, and each is worth buying before the week of.

Death By Disco, October 30 and 31

Thank You For Dancing goes all in for Halloween. Death By Disco runs two nights on one ticket: Friday, October 30, at Recess and City Hall, and Saturday, October 31, at Recess, City Hall and Morgan MFG. Expect head-to-toe decor, a free tattoo and tarot card station, costumed performers roaming every room, several stages and more than 40 DJs. The three rooms sit close together in the West Loop, so plan to hop. Tickets are on the Death By Disco page; check which nights and rooms your tier covers at checkout.

House Calls Halloween Weekend Pass, October 30 to November 1

For house heads, one $75 pass on Dice gets you into all three House Calls shows. Friday, October 30, splits between Alisha at Artifact and Skream playing all night long at the Alhambra, and Saturday, October 31, returns to Artifact with a headliner still to be announced. Doors are at 9 PM and it is 21 and over. Skream’s all-nighter in the Alhambra’s grand old room is the headline.

Hallo-Queen!, Sunday, November 1

Queen!, Chicago’s beloved Sunday house party, takes over the whole building at 3730 N Clark for Hallo-Queen!, an all-building night across Metro and Smartbar with doors at 9 PM. Derrick Carter and Michael Serafini lead a lineup with house pioneer Chip E, DJ Minx, Chris Cruse and CZBoogie. Lucy Stoole and Nico host, Jaharia guest hosts, and Boxboy Rich builds the installations. It is the costume party for people who would rather dance than pose, and tickets are through Smartbar’s event page.

Soho House Chicago’s Halloween party, Skin Deep, is on Saturday, October 31, from 8 PM, for members and their guests.

November’s gala season: the nights worth dressing for

A full house inside the Harris Theater for Music and Dance in Chicago under stage lights — The Harris Theater for Music and Dance, where the Soul Train Awards tape on November 5. Photo: Punzunltd / Wikimedia Commons. CC BY-SA 4.0.

Once the costumes come off, the formalwear comes out. The first big one arrives before Halloween.

Celebrity Chef Ball, Friday, October 23

Meals on Wheels Chicago’s Celebrity Chef Ball takes over The Geraghty, 2520 S Hoyne Ave, on Friday, October 23, with more than fifty chefs cooking a six-course dinner served tableside. It is the city’s biggest food night of the fall, with tickets on the Meals on Wheels Chicago site.

Then two nights in the first half of November give Chicago its biggest dress-up moments before the holidays.

Soul Train Awards, Thursday, November 5

The Soul Train Awards are coming home. BET brings its R&B and soul awards show back to Chicago, the city where Soul Train began, and tapes it at the Harris Theater for Music and Dance, 205 E Randolph St, on Thursday, November 5. Anthony Anderson hosts, Jesse Collins Entertainment produces, and BET president Louis Carr is a Chicago native. The show airs Friday, November 27, at 8 PM on BET and CBS. Public audience tickets and after-parties have not been announced, so for now, save November 27 for the broadcast, and expect a starrier Loop the week of the taping, with artists and their crews in town.

25th PAWS Chicago Fur Ball, Friday, November 13

The PAWS Chicago Fur Ball turns 25 this year, and it remains the most charming black-tie night on the calendar. Guests and their dogs walk the red carpet at The Drake Hotel, 140 E Walton Pl, from 6 PM to midnight on Friday, November 13. The night brings silent and live auctions, a raffle, dinner buffets and dancing in the hotel’s ballrooms, plus a special buffet where the dogs eat out of crystal goblets. Nan and Wayne Kocourek are the presenting sponsors, and the evening raises money for PAWS Chicago’s lifesaving work for homeless pets. Admission starts at $1,000 for one human guest and one dog, human guests must be 21 or older, and tickets are on the Fur Ball page. This is the gala to book ahead.

Opening soon: three rooms on the radar

Three new nightlife rooms are getting close, and none has announced an opening date yet. 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, the Lima-born Peruvian-Japanese restaurant, is preparing 1101 W Lake St with Kero Bar, a cocktail lounge with weekend DJs, built in. And in River North, The Lake at 205 W Superior St is shaping up as a five-story private members’ club with restaurants, cocktail bars, a wine cellar and a roof terrace.

Your two weeks at a glance

Thu to Sun through Mar 14, 2027: Sip & Guzzle at Mile High Cocktail Club, Four Seasons, 5 to 10 PM, $85 with two cocktails
Fridays, Saturdays and Sundays: Kermess, Premonitions Inc., 32 W Randolph St, Floor 14, $89 to $149
Sat Oct 17: Field Museum Gala, Stanley Field Hall
Sat Oct 17: Gordo x Metro B2B at TAO Chicago, 10 PM to 4 AM, 21+, from $22.40
Fri Oct 23: Celebrity Chef Ball, The Geraghty
Sat Oct 24: Red Bull Setlist with Lil Yachty, Radius, doors 7 PM, 18+
Fri Oct 30: Death By Disco at Recess and City Hall; House Calls with Alisha at Artifact and Skream at the Alhambra
Sat Oct 31: Death By Disco at Recess, City Hall and Morgan MFG; House Calls at Artifact; Kermess at 7:30 PM
Sun Nov 1: Hallo-Queen! at Metro and Smartbar, doors 9 PM
Thu Nov 5: Soul Train Awards taping, Harris Theater
Fri Nov 13: 25th PAWS Chicago Fur Ball, The Drake, 6 PM to midnight, from $1,000

Frequently asked questions

What are the best Halloween parties in Chicago in 2026?

Death By Disco runs October 30 at Recess and City Hall and October 31 at Recess, City Hall and Morgan MFG on one ticket. House Calls sells a $75 weekend pass with Skream all night at the Alhambra, and Hallo-Queen! fills Metro and Smartbar on Sunday, November 1, from 9 PM.

When is Halloween weekend in Chicago in 2026?

Halloween 2026 falls on Saturday, October 31, so Chicago’s party weekend runs Friday, October 30, through Sunday, November 1. Death By Disco and House Calls cover Friday and Saturday, Kermess has 7:30 PM shows both nights, and Hallo-Queen! at Metro and Smartbar closes the weekend on Sunday night.

How much is the House Calls Halloween Weekend Pass in Chicago?

The House Calls Halloween Weekend Pass is $75 on Dice and covers three shows: Alisha at Artifact and Skream all night long at the Alhambra on Friday, October 30, 2026, plus a Saturday, October 31, night at Artifact. Doors are at 9 PM and every show is 21 and over.

How much are tickets to Kermess Chicago?

Seats for Premonitions Inc. at Kermess Chicago are Classic $89, Preferred $119 and VIP $149, with food and drinks ordered separately. The 90-minute show plays in a Belgian Spiegeltent on Floor 14 of 32 W Randolph St in the Loop, is 21 and over, and has shows on October 30 and 31, 2026.

Can you buy tickets to the 2026 Soul Train Awards in Chicago?

Public audience tickets for the 2026 Soul Train Awards have not been announced. BET tapes the show at the Harris Theater for Music and Dance, 205 E Randolph St in Chicago, on Thursday, November 5, 2026, with Anthony Anderson hosting, and it airs November 27 at 8 PM on BET and CBS.

When is the PAWS Chicago Fur Ball in 2026?

The 25th PAWS Chicago Fur Ball is Friday, November 13, 2026, from 6 PM to midnight at The Drake Hotel in the Gold Coast. It is a pet-friendly black-tie gala, admission starts at $1,000 for one human guest and one dog, and human guests must be 21 or older.

Chicago Nightlife, Oct 17 to Nov 1: Halloween Tickets to Book Now and the November Galas Worth Dressing For

Just opened: start with the two new rooms

Your rooms for the weeknights in between

Saturday, October 24: Lil Yachty at Radius