Our picks for events in and around Chicago this weekend.
Arts in the Dark
Chicago excels at nighttime parades. Arts in the Dark lights up the city this weekend, with its 11th annual tribute to Halloween as an “artist’s holiday,” presented by the nonprofit LUMA8. Cultural organizations from across the city come together to stage a State Street parade in the heart of the Loop, featuring creative floats, puppets and performances.
6-8 p.m. Oct. 18 on State Street from Lake Street to Van Buren; free, more information at artsinthedark.com
Chicago International Film Festival
“One Golden Summer,” Kevin Shaw’s documentary about Chicago’s 2014 Jackie Robinson West becoming the first all-Black team to win the Little League U.S. Baseball Championship, opened the festival and you still have a couple more chances to catch a screening. It joins a packed lineup featuring films by Kelly Reichardt (who will appear in person for a retrospective of her work), Bradley Cooper, Guillermo del Toro, Gus Van Sant, Noah Baumbach, Yorgos Lanthimos, Richard Linklater and more. It culminates on Oct. 24 with “An Evening With Spike Lee,” where the visionary director will receive the festival’s Lifetime Achievement Award.
Through Oct. 26 in various locations; tickets from $17 at chicagofilmfestival.com
Open House Chicago
For the 15th year, the Chicago Architecture Center is hosting an opportunity to glimpse the interiors of more than 200 culturally significant structures across the city. From Beverly to Rogers Park and select suburbs beyond, Open House Chicago is one of the largest architecture and urban exploration festivals. New this year: the late Steve Albini’s Electrical Audio recording studio, University of Chicago Divinity School’s Swift Hall, Andersonville’s Chicago Magic Lounge, Four Star Mushrooms indoor farm in West Town, the Japanese American Service Committee in West Ridge, and Bronzeville’s South Side Sanctuary. Check out suggested itineraries to plan your weekend.
Oct. 18-19 in various locations; details on the free event at architecture.org
Brandy and Monica
Celebrating the 25th anniversary of their blockbuster R&B duet, “The Boy Is Mine,” Brandy and Monica roll into the United Center this weekend. Special guests Kelly Rowland, Muni Long and Jamal Roberts also will perform. Four Grammy winners and an American Idol, all on one stage.
8 p.m. Oct. 18 at United Center, 1901 W. Madison St.; tickets from $120.60 at unitedcenter.com
Lainey Wilson
Next month, Lainey Wilson will host the Country Music Awards for the second year — and find out if she wins any of the six for which she’s nominated. Will she take entertainer of the year again? You can judge for yourself this weekend. The Louisiana native performs live on her “Whirlwind” tour, with guests Muscadine Bloodline and Maddox Batson.
7 p.m. Oct. 17 at Allstate Arena, 6920 N. Mannheim Road, Rosemont; tickets from $173.95 at rosemont.com
Adam Sandler
You’ve got two options to catch Adam Sandler in Chicago this weekend: live or on screen. He brings his “You’re My Best Friend” tour to the United Center, promising a night of his special brand of relaxed musical comedy. Or you can also catch him in a Chicago International Film Festival screening of the new Noah Baumbach film, “Jay Kelly.” It’s generating the kind of Oscar buzz that may require Sandler to wear something snazzier than a hoodie to this year’s awards.
7:30 p.m. Oct. 20 at United Center, 1901 W. Madison St.; tickets from $50.15 at unitedcenter.com
Janeane Garofalo
Speaking of Gen X fixtures, Janeane Garofalo takes the stage at the Den Theatre this weekend. Expect the comedian, actress and former Air America Radio host to offer her signature deadpan critiques of American pop culture.
7:15 p.m. Oct. 17 at Den Theatre, 1331 N. Milwaukee Ave.; tickets from $22 (2 item minimum) at thedentheatre.com
Sweetest Day Comedy Jam
Bill Bellamy is back with another Sweetest Day Comedy Jam at Wintrust Arena. This year’s lineup features Bellamy along with Lavell Crawford, Tony Roberts, TK Kirkland, Navv Greene, Kevin Tate and Skeet Carter.
8 p.m. Oct. 18 at Wintrust Arena, 200 E. Cermak Road; tickets from $78.45 at wintrustarena.com
Nelson Algren Party
Raise a toast to Chicago literature, Nelson Algren’s “Man With the Golden Arm” marks the 75th anniversary of winning the National Book Award. Or celebrate the news that Bradley Cooper plans to make a biopic about the late author. Algren is still beloved here, so much so that a party will be held this weekend in his honor. Sing songs of protest with Zosia Holden and David Witter, hear Algren historian (and former Tribune staffer) Mary Wisniewski discuss “Chicago: City on the Make,” and watch a film by Tom Palazzolo and see actor Gary Houston perform. Plus, there’s cake.
2-5:30 p.m. Oct. 19 at Clara, 2027 W. North Ave.; $10 suggested donation (adults 21+); details at clarachicago.com
Puppy Yoga benefit for One Tail at a Time
This puppy yoga event benefits One Tail at a Time, a local pet rescue. Stretch and cuddle your way through a special 40-minute yoga class 94 floors above the city in the building formerly known as the John Hancock. The class will be followed by puppy playtime, drinks and (of course) adoption information.
7:45 -8:45 a.m. Oct. 19 at 360 Chicago, 875 N. Michigan Ave.; tickets $75 at 360chicago.com